- Thallium(III) p-tosylate-mediated oxidative [1,2] rearrangement of 2-naphthyl and 2-heteroarylchromanones
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A practical and effective approach towards the synthesis of 3-heteroaryl-4H-chromen-4-ones by the oxidative [1,2] rearrangement of the respective 2-heteroaryl chroman-4-ones using thallium(III) p-tosylate is presented. The oxidative rearrangement of α- an
- Kurapati, Chidvilas,Muthukrishnan, Murugan,Singh, Om V.,Gundla, Rambabu
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supporting information
p. 172 - 177
(2021/10/29)
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- Design, synthesis and structural confirmation of a series of 2-(thiophen-2-yl)- 4h-chromen-3-yl-sulfonate derivatives and preliminary investigation of their antioxidant and anticancer potentials
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A series of novel 2-(thiophen-2-yl)-4H-chromen-3-yl-sulfonate derivatives (4a-4n) were synthesized and investigated for their in vitro free radical scavenging potential as well as cytotoxic efficacies against selected cancer cell lines. The cytotoxicity of the 4H-chromene derivatives (4a-4n) was evaluated according to three human cancer cell lines (HepG2, A549, HeLa) by utilizing a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Accordingly, part of the results exhibited better cytotoxic activities than that of the positive controls (4H-chromen-4-one and apigenin). Among them, compounds 4c-4g exhibited better training to the positive control against the three human cancer cell lines (half maximal inhibitory concentration (IC50) = 3.87 ± 0.12 to 21.38 ± 0.52 μM). Moreover, the extract of the 4H-chromene derivatives (4a-4n) showed better activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis-3-ethylbenzothiazoline- 6-sulfonic acid (ABTS) in antioxidant assays compared to that of the positive control ascorbic acid (IC50 = 12.72 ± 0.27, 5.09 ± 0.21 μg mL-1). Thus, it can be confirmed from the bioassay results that the overall structural design, as well as proper substitution, is crucial in delivering anticipated biological effects. In this regard, spectroscopic techniques such as 1H nuclear magnetic resonance (NMR), 13C NMR, and high-resolution mass spectrometry (HRMS) were also carried out to confirm the final structures.
- Bu, Ming,Han, Lu,Lv, Zhen,Yang, Jifang,Zang, Jialin
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p. 1780 - 1788
(2021/08/05)
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- Convenient synthesis of flavanone derivatives via oxa-Michael addition using catalytic amount of aqueous cesium fluoride
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A total of 36 flavanones, which included polycyclic aromatic and heterocyclic rings, were readily synthesized via oxa-Michael addition from the corresponding hydroxychalcones with a catalytic amount of aqueous cesium fluoride solution under mild conditions. This method could be applied to the scalable synthesis of eriodictyol as a known potent inhibitor of the SARS-CoV-2 spike protein.
- Miura, Motofumi,Shigematsu, Karin,Toriyama, Masaharu,Motohashi, Shigeyasu
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supporting information
(2021/10/25)
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- Structural and spectroscopic analysis and evaluation of cytotoxic activity of 2-hydroxychalcones against human cancer cell lines
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Chalcones and their derivatives exhibit a broad spectrum of pharmacological activities, including antiproliferative activities. Accordingly, they are deemed robust anticancer candidates for cytotoxicity assays. Herein, we synthesized and characterized fou
- Almeida-Neto, Francisco W. Q.,Bandeira, Paulo N.,Barreto, Ant?nio C. H.,Barros-Nepomuceno, Francisco W. A.,Juli?o, Murilo S. S.,Leal, Antonio L. A. B.,Marinho, Emmanuel S.,Pessoa, Claudia,Pinheiro, Daniel P.,Teixeira, Alexandre M. R.,da Silva, Priscila T.,de Lima-Neto, Pedro,de Paiva, Aldeneide S.,dos Santos, Hélcio S.
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- Antischistosomal properties of aurone derivatives against juvenile and adult worms of Schistosoma mansoni
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Schistosomiasis is a neglected disease caused by helminth flatworms of the genus Schistosoma, affecting over 240 million people in more than 70 countries. The treatment relies on a single drug, praziquantel, making urgent the discovery of new compounds. A
- Pereira, Vinicius R.D.,da Silveira, Lígia S.,Mengarda, Ana C.,Alves Júnior, Ismael J.,da Silva, Ohana Oliveira Zuza,Miguel, Fábio Balbino,Silva, Marcos P.,Almeida, Ayla das C.,Torres, Daniel da Silva,Pinto, Priscila de F.,Coimbra, Elaine S.,de Moraes, Josué,Couri, Mara R.C.,da Silva Filho, Ademar A.
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- A novel one-pot synthesis of flavones
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In this paper, a one-pot facile route for the BiCl3/RuCl3-mediated synthesis of functionalized flavones is described, including: (i) intermolecularortho-acylation of substituted phenols with cinnamoyl chlorides, and (ii) intramolecular cyclodehydrogenation of the resultingo-hydroxychalcones. The reaction conditions are discussed herein.
- Chang, Meng-Yang,Tsai, Min-Chen,Lin, Chun-Yi
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p. 11655 - 11662
(2021/03/31)
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- Exploring 3-hydroxyflavone scaffolds as mushroom tyrosinase inhibitors: synthesis, X-ray crystallography, antimicrobial, fluorescence behaviour, structure-activity relationship and molecular modelling studies
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To explore new scaffolds as tyrosinase enzyme inhibitors remain an interesting goal in the drug discovery and development. In due course and our approach to synthesize bioactive compounds, a series of varyingly substituted 3-hydroxyflavone derivatives (1-23) were synthesized in one-pot reaction and screened for in?vitro against mushroom tyrosinase enzyme. The structures of newly synthesized compounds were unambiguously corroborated by usual spectroscopic techniques (FTIR, UV-Vis, 1H-, 13C-NMR) and mass spectrometry (EI-MS). The structure of compound 15 was also characterized by X-ray diffraction analysis. Furthermore, the synthesized compounds (1-23) were evaluated for their antimicrobial potential. Biological studies exhibit pretty good activity against most of the bacterial-fungal strains and their activity is comparable to those of commercially available antibiotics i.e. Cefixime and Clotrimazole. Amongst the series, the compounds 2, 4, 5, 6, 7, 10, 11, 14 and 22 exhibited excellent inhibitory activity against tyrosinase, even better than standard compound. Remarkably, the compound 2 (IC50 = 0.280 ± 0.010 μg/ml) was found almost sixfold and derivative 5 (IC50 = 0.230 ± 0.020 μg/ml) about sevenfold more active as compared to standard Kojic acid (IC50 =1.79 ± 0.6 μg/ml). Moreover, these synthetic compounds (1-23) displayed good to moderate activities against tested bacterial and fungal strains. Their emission behavior was also investigated in order to know their potential as fluorescent probes. The molecular modelling simulations were also performed to explore their binding interactions with active sites of the tyrosinase enzyme. Limited structure-activity relationship was established to design and develop new tyrosinase inhibitors by employing 2-arylchromone as a structural core in the future. Communicated by Ramaswamy H. Sarma.
- Ashraf, Jamshaid,Mughal, Ehsan Ullah,Sadiq, Amina,Bibi, Maryam,Naeem, Nafeesa,Ali, Anser,Massadaq, Anam,Fatima, Nighat,Javid, Asif,Zafar, Muhammad Naveed,Khan, Bilal Ahmad,Nazar, Muhammad Faizan,Mumtaz, Amara,Tahir, Muhammad Nawaz,Mirzaei, Masoud
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p. 7107 - 7122
(2020/08/21)
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- Substituent-Controlled Divergent Cascade Cycloaddition Reactions of Chalcones and Arylalkynols: Access to Spiroketals and Oxa-Bridged Fused Heterocycles
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Herein, we report substituent-controlled divergent cascade cycloaddition reactions of chalcones and arylalkynols in the presence of PtI2. Depending on the substituent on the chalcone, either spiroketals or oxa-bridged fused heterocycles could be obtained in the ranges of 86–97% and 87–95% yields under identical reaction conditions. Control experiments were carried out to elucidate the origin of the high chemoselectivity. These provide a method for the synthesis of a diverse array of structurally complex oxygen-containing heterocycles. (Figure presented.).
- Chang, Weixing,Kong, Jingyang,Li, Jing,Liu, Lingyan,Wang, Hongkai,Zeng, Tianlong
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supporting information
p. 4024 - 4032
(2021/07/12)
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- Glycolytic inhibition and antidiabetic activity on synthesized flavanone scaffolds with computer aided drug designing tools
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Background: Diabetes mellitus is a challengeable metabolic disorder that leads to a group of complications when the HbA1c level is not maintained. Most of the existing drugs avail-able in the market in long-term use may lead to serious adverse effects. He
- Kiruthiga, Natarajan,Saravanan, Govindaraj,Selvinthanuja, Chellappa,Sivakumar, Thangavel,Srinivasan, Kulandaivel
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p. 574 - 592
(2021/09/30)
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- Synthesis and antibacterial activity of chalcone derivatives containing thioether triazole
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The infection of Xanthomonas oryzae pv. Oryzae (Xoo), Ralstonia solanacearum (Rs), and Xanthomonas axonopodis pv. Citri (Xac) has become a major problem in agricultural production. In this study, a series of novel chalcone derivatives containing thioether triazoles were designed and synthesized. The structures of the novel compounds were systematically characterized via 1H-NMR, 13C-NMR, and HRMS. Moreover, the antibacterial activity results showed that E10, E11, E15, and E16 have adequate antibacterial activities against Xoo, Rs, and Xac. Among the different compounds, E15 exhibited remarkable inhibitory effect against Xac with an EC50 of 9.1 μg.mL-1, which was better than that of commercial agent bismerthiazol (54.9 μg.mL-1). In addition, the possible antibacterial mechanism of the target compound E15 against Xac was studied via scanning electron microscopy (SEM).
- Chen, Mei,Chen, Ying,He, Jun,He, Ming,Li, Pu,Su, Shijun,Wang, Hua,Xue, Wei
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- Chiral Hydroxytetraphenylene-Boron Complex Catalyzed Asymmetric Diels-Alder Cycloaddition of 2′-Hydroxychalcones
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(S)-2,15-Cl2-DHTP-boron complex catalyst for the asymmetric Diels-Alder cycloaddition of 2′-hydroxychalcones and dienes was developed and tested. The resulting cyclohexenes with three chiral centers were obtained in high yields (up to 98%) with excellent stereoselectivities (up to >20:1 endo/exo, >99% ee). This catalytic system features high efficiency, broad substrate scopes, and mild reaction conditions. In addition, a DFT study was performed to explain the stereochemical course of the asymmetric induction.
- Chai, Guo-Li,Qiao, Yan,Zhang, Ping,Guo, Rong,Wang, Juan,Chang, Junbiao
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supporting information
p. 8023 - 8027
(2020/11/02)
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- Novel chalcone and flavone derivatives as selective and dual inhibitors of the transport proteins ABCB1 and ABCG2
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During cancer chemotherapy, certain cancers may become cross-resistant to structurally diverse antineoplastic agents. This so-called multidrug resistance (MDR) is highly associated with the overexpression of ATP-binding cassette (ABC) transport proteins. These membrane-bound efflux pumps export a broad range of structurally diverse endo- and xenobiotics, including chemically unrelated anticancer agents. This translocation of drugs from the inside to the outside of cancer cells is mediated at the expense of ATP. In the last 40 years, three ABC transporters – ABCB1 (P-gp), ABCC1 (MRP1), and ABCG2 (BCRP) – have mainly been attributed to the occurrence of MDR in cancer cells. One of the strategies to overcome MDR is to inhibit the efflux transporter function by small-molecule inhibitors. In this work, we investigated new chalcone- and flavone-based compounds for selective as well as broad-spectrum inhibition of the stated transport proteins. These include substituted chalcones with variations at rings A and B, and flavones with acetamido linker at position 3. The synthesized molecules were evaluated for their inhibitory potential against ABCB1, ABCC1, and ABCG2 in calcein AM and pheophorbide A assays. In further investigations with the most promising candidates from each class, we proved that ABCB1- and ABCG2-mediated MDR could be reversed by the compounds. Moreover, their intrinsic toxicity was found to be negligible in most cases. Altogether, our findings contribute to the understanding of ABC transport proteins and reveal new compounds for ongoing evaluation in the field of ABC transporter-mediated MDR.
- Silbermann, Katja,Shah, Chetan P.,Sahu, Niteshkumar U.,Juvale, Kapil,Stefan, Sven Marcel,Kharkar, Prashant S.,Wiese, Michael
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p. 193 - 213
(2019/01/03)
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- Design, synthesis, and biological evaluation of Helicobacter pylori inosine 5′-monophosphate dehydrogenase (HpIMPDH) inhibitors
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Inosine 5′-monophosphate dehydrogenase (IMPDH) catalyzes a crucial step in the biosynthesis of guanine nucleotides. Being a validated target for immunosuppressive, antiviral, and anticancer drug development, lately it has been exploited as a promising target for antimicrobial therapy. Extending our previous work on Mycobacterium tuberculosis IMPDH, GuaB2, inhibitor development, we screened a set of 23 new chemical entities (NCEs) with substituted flavone (Series 1) and 1,2,3-triazole (Series 2) core structures for their in vitro Helicobacter pylori IMPDH (HpIMPDH) and human IMPDH2 (hIMPDH2) inhibitory activities. All the NCEs possessed acceptable molecular, physicochemical, and toxicity property profiles. The ranges for HpIMPDH and hIMPDH2 inhibition were 9–99.9% and 16–57%, respectively, at 10 μM concentration. The most potent HpIMPDH inhibitor, 25c, exhibited IC50 value of 1.27 μM with no hIMPDH2 inhibitory activity. The moderately potent, structurally novel hit molecule, 25c, may serve as a lead for further design and development of highly potent HpIMPDH inhibitors.
- Sahu, Niteshkumar U.,Purushothaman, Gayathri,Thiruvenkatam, Vijay,Kharkar, Prashant S.
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p. 125 - 132
(2018/11/06)
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- Novel chalcone derivatives containing a 1,2,4-triazine moiety: Design, synthesis, antibacterial and antiviral activities
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A series of novel chalcone derivatives containing the 1,2,4-triazine moiety were synthesized and their structures were confirmed by 1H NMR, 13C NMR and elemental analyses. Antiviral bioassays revealed that most of the compounds exhibited good antiviral activity against tobacco mosaic virus (TMV) at a concentration of 500 μg mL-1. The designated compound 4l was 50% effective in terms of curative and protective activities against TMV with 50% effective concentrations (EC50) of 10.9 and 79.4 μg mL-1, which were better than those of ningnanmycin (81.4 and 82.2 μg mL-1). Microscale thermophoresis (MST) also showed that the binding of compound 4l to coat protein (TMV-CP) yielded a Kd value of 0.275 ± 0.160 μmol L-1, which was better than that of ningnanmycin (0.523 ± 0.250 μmol L-1). At the same time, molecular docking studies for 4l with TMV-CP (PDB code:1EI7) showed that the compound was embedded well in the pocket between the two subunits of TMV-CP. Meanwhile, compound 4a demonstrated excellent antibacterial activities against Ralstonia solanacearum (R. solanacearum), with an EC50 value of 0.1 μg mL-1, which was better than that of thiodiazole-copper (36.1 μg mL-1) and bismerthiazol (49.5 μg mL-1). The compounds act by causing folding and deformation of the bacterial cell membrane as observed using scanning electron microscopy (SEM). The chalcone derivatives thus synthesized could become potential alternative templates for novel antiviral and antibacterial agents.
- Tang, Xu,Su, Shijun,Chen, Mei,He, Jun,Xia, Rongjiao,Guo, Tao,Chen, Ying,Zhang, Cheng,Wang, Jun,Xue, Wei
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p. 6011 - 6020
(2019/03/12)
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- Effective Hydrogenation of 3-(2”-furyl)- And 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-prop-2-en-1-one in Selected Yeast Cultures
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Biotransformations were performed on eight selected yeast strains, all of which were able to selectively hydrogenate the chalcone derivatives 3-(2”-furyl)-(1) and 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-prop-2-en-1-one (3) into 3-(2”-furyl)- (2) and 3-(2”-thi
- ?u zny, Mateusz,Krzywda, Martyna,Koz?owska, Ewa,Kostrzewa-Sus?ow, Edyta,Janeczko, Tomasz
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- Synthesis of 3-HCF2S-Chromones through Tandem Oxa-Michael Addition and Oxidative Difluoromethylthiolation
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A simple protocol for the synthesis of difluoromethylthiolated chromen-4-ones using elemental sulfur and ClCF2CO2Na as the difluoromethylthiolating agent is described. Three-component reactions of 2′-hydroxychalcones, ClCF2CO2Na, and sulfur under basic conditions using TEMPO as the oxidant afforded HCF2S-containing 4H-chromen-4-one and 9H-thieno[3,2-b]chromen-9-one derivatives in good yield. The protocol is practical and efficient, and the starting materials are cheap and readily available.
- Zhang, Pingshun,Chen, Wanzhi,Liu, Miaochang,Wu, Huayue
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supporting information
p. 9326 - 9329
(2019/12/24)
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- From Carbamate to Chalcone: Consecutive Anionic Fries Rearrangement, Anionic Si → C Alkyl Rearrangement, and Claisen-Schmidt Condensation
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A highly efficient one-pot procedure was developed for the synthesis of various 2′-hydroxychalcones from phenyl diethylcarbamate, featuring consecutive Snieckus-Fries rearrangement, anionic Si a?' C alkyl rearrangement, and Claisen-Schmidt condensation in a single operation. The applicability of this protocol was demonstrated by the highly efficient synthesis of the anti-inflammatory natural product lonchocarpin. The mechanism insight is also provided.
- Kumar, Singam Naveen,Bavikar, Suhas Ravindra,Pavan Kumar, Chebolu Naga Sesha Sai,Yu, Isaac Furay,Chein, Rong-Jie
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p. 5362 - 5366
(2018/09/12)
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- Synthesis of a series of chalcones and related flavones and evaluation of their antibacterial and antifungal activities
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Background: A series of chalcones and flavones were synthesized from 2’-hydroxyacetophenone and substituted aromatic aldehydes via Simmons-Schmidt condensation followed by oxidative cyclization. Methods: Characterization of the obtained structures was established on the basis of their spectroscopic data. The synthesized compounds were screened for their antimicrobial activities against five bacterial strains (Citrobacter freundii, Staphylococcus aureus, Listeria monocytogenes, Salmonella braenderup, Escherichia coli.) and two fungal strains (Candida albicans, Candida krusei). Results: The in vitro bioassay results indicated that some target compounds displayed moderate (4d, 4e) to high (4a) antifungal activity against the pathogenic fungi C. albicans and C. krusei. Conclusion: For the antibacterial activity, only products 3d and 4d showed a weak antibacterial activity. These compounds can lead to the design of new drugs with specific antifungal activity.
- Benouda, Hind,Bouchal, Btissam,Challioui, Allal,Oulmidi, Abdelkader,Harit, Tarik,Malek, Fouad,Riahi, Abdelkhalek,Bellaoui, Mohammed,Bouammali, Boufelja
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- Substituted chromene alcohol ester compound and application thereof to preparation of anti-cancer medicines
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The invention relates to a substituted chromene alcohol ester compound and application thereof to preparation of anti-cancer medicines, and belongs to the technical field of synthesis of new medicines. 3-hydroxyflavone is subjected to structural transformation according to the structural characteristic of flavone compounds, a benzene ring at the position of a B ring is replaced by thiophene, the sulfonyl is further introduced into a 3 position to form ester, and a novel (thiophene-2-yl)-4H-chromene-3-sulfonate substituted chromene alcohol ester compound is synthesized. The synthesize (thiophene-2-yl)-4H-chromene-3-sulfonate is subjected to screening and evaluation of three human cancer cell in vitro anti-tumor activities by using an MTT method, and the result indicates that the compound can be used for preparing medicines for inhibiting the growth of tumor cells and inducing tumor cell apoptosis. The tumor cells are human cervical cancer cells HeLa, human liver cancer cells HepG2 and human lung cancer cells A549.
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-
Paragraph 0061; 0062
(2018/11/03)
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- Synthesis, structure-activity relationship and molecular docking studies of 3-O-flavonol glycosides as cholinesterase inhibitors
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The prime objective of this research work is to prepare readily soluble synthetic analogues of naturally occurring 3-O-flavonol glycosides and then investigate the influence of various substituents on biological properties of synthetic compounds. In this context, a series of varyingly substituted 3-O-flavonol glycosides have been designed, synthesized and characterized efficiently. The structures of synthetic molecules were unambiguously corroborated by IR, 1H, 13C NMR and ESI-MS spectroscopic techniques. The structure of compound 22 was also analyzed by X-ray diffraction analysis. All the synthetic compounds (21–30) were evaluated for in vitro inhibitory potential against cholinesterase enzymes. The results displayed that most of the derivatives were potent inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) with varying degree of IC50 values. The experimental results were further encouraged by molecular docking studies in order to explore their binding behavior with the active pocket of AChE and BChE enzymes. The experimental and theoretical results are in parallel with one another.
- Mughal, Ehsan Ullah,Javid, Asif,Sadiq, Amina,Murtaza, Shahzad,Zafar, Muhammad Naveed,Khan, Bilal Ahmad,Sumra, Sajjad Hussain,Tahir, Muhammad Nawaz,Kanwal,Khan, Khalid Mohammed
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p. 3696 - 3706
(2018/06/19)
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- Design, synthesis and MAO inhibitory activity of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives
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A series of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives (aurones, 1–20) were synthesized and screened for their inhibitory activity against hMAO. Seventeen compounds (1–5, 7–17, 19) were found to be selective towards hMAO-B, while two w
- Badavath, Vishnu Nayak,Nath, Chandrani,Ganta, Narayana Murthy,Ucar, Gulberk,Sinha, Barij Nayan,Jayaprakash, Venkatesan
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p. 1528 - 1532
(2017/07/17)
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- Photoreactions of 2-(furan-2-yl)-3-hydroxy-4H-chromen-4-one and 3-hydroxy-2-(thiophene-2-yl)-4 H -chromen-4-one using cyclohexane and acetonitrile as solvents
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Photolysis of the titled chromenones was carried out at their longest absorption band (~360 nm) using cyclohexane (CH) and acetonitrile (ACN) as solvents, in both aerated and de-aerated solutions. Different dimeric photoproducts were formed with both chromenones in aerated solutions. On photolysing 2-(furan-2-yl)-3-hydroxy-4H-chromen-4-one (FHC) in aerated cyclohexane, 2-(furan-2-yl)-2-{[2-(furan-2yl)-4-oxo-4H-chromen-3-yl]oxy}-2H-chromene-3,4-dione (a dehydrodimer) was formed, and on photolysing 3-hydroxy-2-(thiophene-2-yl)-4H-chromen-4-one (THC) in aerated ACN, a different dimeric product was isolated and identified. The corresponding 3-aryl-3-hydroxy-1,2-indandiones were also detected with FHC in ACN and with THC in CH, in addition to the dimeric products in both cases. On the other hand, in the de-aerated solutions, only the corresponding 1,2-indandiones were detected. 3-(Furan-2-yl)isobenzofuran-1(3H)-one as a secondary product was also detected with FHC in both solvents. An attempt was made to isolate the spectra of the photoproducts in situ. Excited State Intramolecular Proton Transfer (ESIPT) and Excited State Intramolecular Charge Transfer (ESICT) processes complicate the photodynamics of the reaction, making it difficult to predict the mechanisms of the photoreactions. However, tentative mechanisms have been proposed for the formation of the photoproducts.
- Kaur, Kulvir,Kaur, Ranbir,Tomar, Jyoti,Bansal, Manisha
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p. 1311 - 1319
(2017/08/16)
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- The synthesis and synergistic antifungal effects of chalcones against drug resistant Candida albicans
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To identify effective and low toxicity synergistic antifungal compounds, 24 derivatives of chalcone were synthesized to restore the effectiveness of fluconazole against fluconazole-resistant Candida albicans. The minimal inhibitory concentration (MIC80) and the fractional inhibitory concentration index (FICI) of the antifungal synergist fluconazole were measured against fluconazole-resistant Candida albicans. This was done via methods established by the clinical and laboratory standards institute (CLSI). Of the synthesized compounds, 2′-hydroxy-4′-methoxychalcone (8) exhibited the most potent in vitro (FICI = 0.007) effects. The structure activity relationship of the compounds are then discussed.
- Wang, Yuan-Hua,Dong, Huai-Huai,Zhao, Fei,Wang, Jie,Yan, Fang,Jiang, Yuan-Ying,Jin, Yong-Sheng
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supporting information
p. 3098 - 3102
(2016/06/13)
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- Extended Aromatic and Heteroaromatic Ring Systems in the Chalcone-Flavanone Molecular Switch Scaffold
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Previous work on the o-hydroxychalcone/flavanone molecular switching scaffold showed that simple substitutions alter the pH range in which rapid interconversion occurs. Herein, more impactful structural modifications were performed via alteration of the characteristic phenyl rings to alternative aromatic systems. It was determined that the scaffold was still viable after these changes and that the range of accessible midpoint pH values was markedly increased. To further explore the switch's scope, scaffolds able to have multiple switching events were also investigated.
- Muller, Brian M.,Litberg, Theodore J.,Yocum, Reid A.,Pniewski, Chanté A.,Adler, Marc J.
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p. 5775 - 5781
(2016/07/13)
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- Excited-state intramolecular proton-transfer reaction demonstrating anti-Kasha behavior
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We report unusual photophysical properties observed on two newly designed 3-hydroxychromone derivatives exhibiting the excited-state intramolecular proton transfer (ESIPT) reaction. The efficiency of ESIPT reaction is greatly enhanced upon excitation with
- Tseng, Huan-Wei,Shen, Jiun-Yi,Kuo, Ting-Yi,Tu, Ting-Syun,Chen, Yi-An,Demchenko, Alexander P.,Chou, Pi-Tai
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p. 655 - 665
(2015/12/30)
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- A new series of 2-phenol-4-aryl-6-chlorophenyl pyridine derivatives as dual topoisomerase I/II inhibitors: Synthesis, biological evaluation and 3D-QSAR study
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As a continuous effort to develop novel antitumor agents, a new series of forty-five 2-phenol-4-aryl-6-chlorophenyl pyridine compounds were synthesized and evaluated for cytotoxicity against four different human cancer cell lines (DU145, HCT15, T47D, and HeLa), and topoisomerase I and II inhibitory activity. Several compounds (10-15, 20, 22, 24, 28, 42, and 49) displayed strong to moderate dual topoisomerase I and II inhibitory activity at 100 μM. It was observed that hydroxyl and chlorine moiety at meta or para position of phenyl ring is favorable for dual topoisomerase inhibitory activity and cytotoxicity. Most of the compounds displayed stronger cytotoxicities than those of all positive controls against the HCT15 and T47D cell lines. For investigation of the structure-activity relationships, a 3D-QSAR analysis using the method of comparative molecular field analysis (CoMFA) was performed. The generated 3D contour maps can be used for further rational design of novel terpyridine derivatives as highly selective and potent cytotoxic agents.
- Karki, Radha,Jun, Kyu-Yeon,Kadayat, Tara Man,Shin, Somin,Thapa Magar, Til Bahadur,Bist, Ganesh,Shrestha, Aarajana,Na, Younghwa,Kwon, Youngjoo,Lee, Eung-Seok
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p. 228 - 245
(2016/03/08)
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- Synthesis and antiviral activity of 2-aryl-4H-chromen-4-one derivatives against Chikungunya virus
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A series of nineteen 2-aryl-4H-chromen-4-one derivatives 2a-2s were synthesized and evaluated for their antiviral activity against Chikungunya virus (LR2006-OPY1) in Vero cell culture by CPE reduction assay. Three compounds 2a, 2b and 2g, were found to be active at concentration of (IC50) 0.44 μM, 0.45 μM and 2.02 μM, respectively. Compounds having heterocyclic ring 2a and 2b at the 2nd position of the chromenone were found to be potent inhibitor of ChikV. Cytotoxicity studies were performed using Vero cell culture, compounds 2a and 2b exhibited SI of ≥100. Molecular docking simulation has been carried out to understand the possible mechanism of action.
- Badavath, Vishnu N.,Jadav, Surender S.,Pastorino, Boris,De Lamballerie, Xavier,Sinha, Barij N.,Jayaprakash, Venkatesan
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p. 1019 - 1024
(2016/11/25)
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- Topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship study of dihydroxylated 2,6-diphenyl-4-aryl pyridines
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Abstract A new series of thirty-six dihydroxylated 2,6-diphenyl-4-aryl pyridines containing hydroxyl groups at the ortho, meta, or para position of 2- and 6-phenyl rings attached to the central pyridine were designed and synthesized. They were evaluated f
- Karki, Radha,Song, Chanju,Kadayat, Tara Man,Magar, Til Bahadur Thapa,Bist, Ganesh,Shrestha, Aarajana,Na, Younghwa,Kwon, Youngjoo,Lee, Eung-Seok
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p. 3638 - 3654
(2015/08/03)
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- Monoamine oxidase inhibitory activity of 2-aryl-4H-chromen-4-ones
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A series of twenty 2-aryl-4H-chromen-4-one (flavones) derivatives (3a-3s) were synthesized and tested for hMAO inhibitory activity. Fifteen compounds (3a, 3c, 3e-3h, 3j-3p, 3r, 3s) were found to be selective towards MAO-B, while 3d was selective towards MAO-A, and 3b, 3i and 3q were non-selective. Experimental Selectivity Index for MAO-B ranges from 2.0 (3g, 3p) to 30.0 (3j). Compound 3j, which is carrying 3,4-di-OMeC6H3 groups at R position on the molecule, was found to be potent MAO-B inhibitor amongst the fifteen with Ki value for MAO-B of 0.16 ± 0.01 lM comparable to that of standard drug, Selegiline (Ki for MAO-B is 0.16 ± 0.01 μM). Compound 3j also appeared as the most selective MAO-B inhibitor according to its best selectivity index (30.0), which is comparable to that of Selegiline (SIMAO-B = 35.0). Molecular docking and molecular dynamics simulation studies were carried out using Autodock-4.0 and Amber12 to understand the molecular level interaction and energy relation of MAO isoforms with selective inhibitors (3d and 3j). Simulation results are in good agreement with the experimental results. Leads identified may further be explored to develop potent isoform specific inhibitors of MAO.
- Nayak, Badavath Vishnu,Ciftci-Yabanoglu,Bhakat, Soumendranath,Timiri, Ajay Kumar,Sinha, Barij N.,Ucar,Soliman, Mahmoud E. S.,Jayaprakash, Venkatesan
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- Monoamine oxidase inhibitory activity of 2-aryl-4H-chromen-4-ones
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A series of twenty 2-aryl-4H-chromen-4-one (flavones) derivatives (3a-3s) were synthesized and tested for hMAO inhibitory activity. Fifteen compounds (3a, 3c, 3e-3h, 3j-3p, 3r, 3s) were found to be selective towards MAO-B, while 3d was selective towards MAO-A, and 3b, 3i and 3q were non-selective. Experimental Selectivity Index for MAO-B ranges from 2.0 (3g, 3p) to 30.0 (3j). Compound 3j, which is carrying 3,4-di-OMeC6H3 groups at R position on the molecule, was found to be potent MAO-B inhibitor amongst the fifteen with Ki value for MAO-B of 0.16 ± 0.01 μM comparable to that of standard drug, Selegiline (Ki for MAO-B is 0.16 ± 0.01 μM). Compound 3j also appeared as the most selective MAO-B inhibitor according to its best selectivity index (30.0), which is comparable to that of Selegiline (SIMAO-B = 35.0). Molecular docking and molecular dynamics simulation studies were carried out using Autodock-4.0 and Amber12 to understand the molecular level interaction and energy relation of MAO isoforms with selective inhibitors (3d and 3j). Simulation results are in good agreement with the experimental results. Leads identified may further be explored to develop potent isoform specific inhibitors of MAO.
- Badavath, Vishnu Nayak,Ciftci-Yabanoglu,Bhakat, Soumendranath,Timiri, Ajay Kumar,Sinha, Barij N.,Ucar,Soliman, Mahmoud E.S.,Jayaprakash, Venkatesan
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- Synthesis and biological evaluation of novel 1,3,5-trisubstituted pyrazolines
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A new series of chalcones (1a-j) was prepared by reacting 2-thiophene carbaldehyde and substituted ketones in alcohol medium in presence of NaOH. The chalcones undergoes selective cyclization with 4-hydroxybenzohydrazide (2) in gl acetic acid medium to yield the title compounds 1,3,5-trisubstituted pyrazolines (3a-j). All the newly synthesized compounds were evaluated for their in-vitro antibacterial and antifungal activities. The structures of the new compounds were assigned on the basis of elemental analysis, 1H NMR, IR and Mass spectral data.
- Revanasiddappa,Jisha,Varghese, Saira Susan,Kalsi, Jasmine,Jose, Neethu
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- Synthesis and cdc25B inhibitory activity evaluation of chalcones
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A library of sixty-five chalcones was prepared for screening against the protein phosphatase, cdc25B. From this library, thirteen compounds were found having good inhibitory activity. Two compounds have excellent activity and can be used for the design of
- Zhao, Fei,Zhao, Qing-Jie,Zhao, Jing-Xia,Zhang, Da-Zhi,Wu, Qiu-Ye,Jin, Yong-Sheng
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p. 206 - 214
(2013/07/26)
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- Intramolecular cyclisation of photolabile thienylchromenones: Synthesis of angular tetracyclic compounds
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Photo-irradiation of 3-alkoxy-2-(thiophen-2-yl)-4H-chromen-4-ones in methanol with Pyrex filtered UV-light lead to the formation of interesting angular tetracyclic compounds. In the present study, we demonstrate the formation and distribution of the photoproducts which depends upon the stability of in situ generated 1,4-biradicals (through type-II process).
- Kamboj, Ramesh C.,Pratibha,Kumar, Dinesh,Sharma, Geeta,Arora, Rita,Kumar, Parvin,Kumar, Suresh,Kumar, Ramesh,Kamal, Raj
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p. 481 - 487
(2013/11/06)
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- Synthesis and characterization of Ru(II)-DMSO-Cl-chalcone complexes: DNA binding, nuclease, and topoisomerase II inhibitory activity
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The complexes of type cis-[Ru(S-DMSO)3(R-CO-CH-CH-R′)Cl] (R = 2-hydroxyphenyl for all, R′ = phenyl 1, naphthyl 2, anthracenyl 3, thiophene 4, 3-methyl thiophene 5) are synthesized and characterized using spectroscopic (IR, 1H and su
- Gaur, Ruchi,Mishra, Lallan
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scheme or table
p. 3059 - 3070
(2012/04/23)
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- Synthesis and screening antimicrobial activities of novel 1,3-diaryl-3-(phenylthio)propan-1-one derivatives
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In this study, a series of novel β-mercapto carbonyl derivatives (3a-j) was prepared by addition of thiophenol (2) to chalcones (1a-j) in the presence of catalytic amount of iodine (10 mol%) in CH2Cl 2. Antibacterial and antifungal in vitro properties of the synthesized compounds were tested against some human pathogenic microorganisms by employing the disk diffusion technique. For the most active compounds, also minimum inhibitory concentrations (MICs) were determined. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
- Karaman, Isa,Gezegen, Hayreddin,Ceylan, Mustafa,Dilma, Merve
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experimental part
p. 580 - 586
(2012/06/01)
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- An unexpected rearrangement-hydration reaction sequence of 2H-chromenes to dihydrochalcones under catalysis of HAuCl4
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2-Aryl-2H-chromenes in aqueous DCM medium under catalysis of HAuCl 4 are converted into 3-(2-hydroxyaryl)-1-arylpropan-1-ones through hydration-rearrangement reaction sequence in very good yield. The key step probably involves the [1,5] hydride shift followed by the hydrolysis under the reaction condition. The notable advantages of this method are operational simplicity and ease of isolation of products and also provide a pathway to convert the chalcone into DHCs with the transposition of carbonyl group. 2012 Elsevier Ltd. All rights reserved.
- Maiti, Gourhari,Kayal, Utpal,Karmakar, Rajiv,Bhattacharya, Rudraksha N.
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p. 6321 - 6325,5
(2012/12/12)
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- Synthesis and anti-bacterial activity of some heterocyclic chalcone derivatives bearing thiofuran, furan, and quinoline moieties
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36 Novel heterocyclic chalcone derivatives were synthesized and tested for their anti-bacterial activity. Some compounds presented good anti-microbial activities against Gram-positive bacteria (including the multidrug-resistant clinical isolates). This cl
- Zheng, Chang-Ji,Jiang, Sheng-Ming,Chen, Zhen-Hua,Ye, Bai-Jun,Piao, Hu-Ri
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experimental part
p. 689 - 695
(2012/06/01)
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- Ionic liquid mediated Cu-catalyzed cascade oxa-Michael-oxidation: Efficient synthesis of flavones under mild reaction conditions
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Flavonoids are a class of natural products, found in a wide range of vascular plants and dietary components. Their low toxicity and extensive biological activities, including anti-cancer and anti-bacterial, have made them attractive candidates to serve as therapeutic agents for many diseases. Herein, we disclose a highly efficient synthetic method of CuI-catalyzed cascade oxa-Michael-oxidation, using chalcones as substrates, mediated by the ionic liquid [bmim][NTf2] at a low temperature. This efficient synthetic method has demonstrated high synthetic utility and can afford flavones in good to high yields (up to 98%).
- Du, Zhiyun,Ng, Huifen,Zhang, Kun,Zeng, Huaqiang,Wang, Jian
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supporting information; experimental part
p. 6930 - 6933
(2011/11/04)
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- Screening of biological activities of a series of chalcone derivatives against human pathogenic microorganisms
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In an effort to develop new antimicrobial agents, a series of chalcone derivatives, 3-60, were prepared by Claisen-Schmidt condensation of appropriate acetophenones and 2-furyl methyl ketones with appropriate aromatic aldehydes, furfural, and thiophene-2-carbaldehyde in an aqueous solution of NaOH and EtOH at room temperature. The synthesized compounds were characterized by means of their IR- and NMR-spectral data, and elemental analysis. All compounds were tested for their antibacterial and antifungal activities by the disc diffusion method. For the most active compounds, also minimum inhibitory concentrations (MICs) were determined.
- Karaman, Isa,Gezegen, Hayreddin,Guerdere, M. Burcu,Dingil, Alparslan,Ceylan, Mustafa
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experimental part
p. 400 - 408
(2010/09/04)
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- Identification of chalcones as in vivo liver monofunctional phase II enzymes inducers
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Cancer preventive agents (CPA) are drugs able to suppress the carcinogen metabolic activation or block the formation of ultimate carcinogens. CPA could act through various molecular mechanisms, for example by interfering with the action of procarcinogen. This could be attained by increasing the phase II enzymes levels of quinone reductase (QR) and glutathione S-transferase (GST). New flavonoids, especially chalcones, have been identified as in vivo monofunctional phase II enzymes inducers. Oral administration of chalcone, 4, and both p-methoxy-substituted chalcones, 6 and 14, increased hepatic QR activity with concomitant decrease in CYP1A1 activity, a member of the most important group of phase I enzymes cytochrome P450. Among them, 4 also increased GST activity. While p-bromo-substituted chalcone 8 was the best inducer of QR it decreased hepatic GST expression and cytochrome P450, being the most effective decreasing cytochrome P450-expression. Thienyl-chalcone 20 being the bioisostere of chalcone 4 did not display the same in vivo profile in the phase I level modification. As chalcone 4 its bioisostere, chalcone 20, displayed low DNA strand breakage and absence of mutagenicity. Also, in our preliminary in vivo tumourigenesis/chemopreventive and acute-toxicity studies, chalcones 4, 6 and 8 showed the best behaviours as CPA justifying additional studies that are ongoing.
- Cabrera, Mauricio,Lavaggi, Maria Laura,Croce, Fiorela,Celano, Laura,Thomson, Leonor,Fernandez, Marcelo,Pintos, Cristina,Raymondo, Stella,Bollati, Mariela,Monge, Antonio,Lopez De Cerain, Adela,Piro, Oscar E.,Cerecetto, Hugo,Gonzalez, Mercedes
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scheme or table
p. 5391 - 5399
(2010/09/11)
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- Small molecules with structural similarities to siderophores as novel antimicrobials against Mycobacterium tuberculosis and Yersinia pestis
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Drugs inhibiting the iron scarcity-induced, siderophore-mediated iron-scavenging systems of Mycobacterium tuberculosis (Mtb) and Yersinia pestis (Yp) may provide new therapeutic lines of defense. Compounds with structural similarities to siderophores were synthesized and evaluated as antimicrobials against Mtb and Yp under iron-limiting conditions, which mimic the iron scarcity these pathogens encounter and must adapt to in the host, and under standard iron-rich conditions for comparison. New antimicrobials were identified, some of which warrant exploration as initial leads against potentially novel targets and small-molecule tools to assist in the elucidation of targets specific to iron-scarcity adapted Mtb and Yp.
- Stirrett, Karen L.,Ferreras, Julian A.,Jayaprakash, Venkatesan,Sinha, Barij N.,Ren, Tao,Quadri, Luis E.N.
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p. 2662 - 2668
(2008/12/21)
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- Pyrazoline-based mycobactin analogues as MAO-inhibitors
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3,5-Diaryl carbothioamide pyrazolines designed as mycobactin analogs (mycobacterial siderophore) were reported to be potent antitubercular agents under iron limiting condition in our earlier study. Clinical complications of newly introduced antibiotic Linezolid, due its MAO inhibitory activity, prompted us to evaluate our compounds for their MAO-inhibitory activity against rat liver MAO-A and MAO-B as pyrazolines were reported to be antidepressants and MAO inhibitors. The present study carried out with this pilot library of 32 compounds will provide us with necessary information for designing antitubercular molecules with reduced MAO-inhibitory activity and also help us in identifying a selective MAO-B inhibitor which has potential clinical utility in neurodegenerative disorders. Thirty-two compounds analyzed has shown spectrum of activity from selective to nonselective against two isoforms of rat liver MAO-A and MAO-B and also as competitive, reversible to non-competitive, irreversible. It is also interesting to note that anti-tubercular compound 11, 14 and 16 were also found to be selective inhibitors of rat liver MAO-B. Docking studies with human MAO shows that compound 11 interacts with the catalytic site of both the isoforms, suggesting compound 11 as nonselective inhibitor of human MAO isoforms.
- Jayaprakash, Venkatesan,Sinha, Barij N.,Ucar, Gulberk,Ercan, Ayse
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scheme or table
p. 6362 - 6368
(2009/09/30)
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- Synthetic chalcones as potential anti-inflammatory and cancer chemopreventive agents
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In an effort to develop potent anti-inflammatory and cancer chemopreventive agents, a series of chalcones were prepared by Claisen-Schmidt condensation of appropriate acetophenones with suitable aromatic aldehyde or prepared with appropriate dihydrochalco
- Won, Shen-Jeu,Liu, Cheng-Tsung,Tsao, Lo-Ti,Weng, Jing-Ru,Ko, Horng-Huey,Wang, Jih-Pyang,Lin, Chun-Nan
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p. 103 - 112
(2007/10/03)
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- Development of novel pesticides based on phytoalexins: Part 2. Quantitative structure-activity relationships of 2-heteroaryl-4-chromanone derivatives
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Phytoalexins are low-molecular-weight chemicals that immune systems of plants produce and accumulate in response to infections, especially those of fungal origin. Although their content is not high in plants, yet they have shown unique fungicidal activity
- Yang, Guangfu,Jiang, Xiaohua,Yang, Huazheng
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p. 1063 - 1067
(2007/10/03)
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- A concerted synthesis of hydroxychalcones, flavanones and benzo[b]furans through palladium-catalysed reactions
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A convenient palladium-catalysed procedure for the synthesis of o-hydroxychalcones, flavanones and benzo[b]furans is described where o-iodophenyl acetate was used as a common precursor.
- De, Mahuya,Majumdar, Dyuti P.,Kundu, Nitya G.
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p. 665 - 674
(2007/10/03)
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- Aminopropanol derivatives of substituted 2-hydroxy-propiophenones, and therapeutic agents containing these compounds
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Aminopropanol derivatives of the formula: STR1 where R1 and R2 are identical or different and are each hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl or hydroxyalkyl, each of not more than 6 carbon atoms, alkoxyalkyl, alkylthioalkyl o
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- Thienyl acrylamides and thienyl pyrazolines as potential schistosomicidal agents
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α Thienyl N substituted acrylamides that possess analogous structures to known schistosomicidal agents were synthesized. Two chalcones were prepared by condensing α thiophenealdehyde and acetophenone or its o hydroxy derivative. Cyclization of the chalcon
- El Kerdawy,Samour,El Agamey
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