- Design and synthesis of chromone-nitrogen mustard derivatives and evaluation of anti-breast cancer activity
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Chromone has emerged as one of the most important synthetic scaffolds for antitumor activity, which promotes the development of candidate drugs with better activity. In this study, a series of nitrogen mustard derivatives of chromone were designed and syn
- Sun, Jianan,Mu, Jiahui,Wang, Shenglin,Jia, Cai,Li, Dahong,Hua, Huiming,Cao, Hao
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p. 431 - 444
(2022/01/04)
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- Synthesis of Chromeno[2,3-d]pyrimidin-5-one Derivatives from 1,3,5-Triazinanes via Two Different Reaction Pathways
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1,3,5-Triazinanes, as a kind of versatile building block, are applied in the synthesis of chromeno[2,3-d]pyrimidin-5-one derivatives via two different reaction modes, which perfectly exhibits the powerful function of 1,3,5-triazinane as a three-atom synth
- Wang, Taimin,Zhang, Biwei,Hu, Lin,Sun, Haiyan,Wang, Yan,Zhai, Hongbin,Cheng, Bin
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p. 1348 - 1356
(2022/01/27)
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- Chromone 3-position nitric oxide donor derivative as well as preparation method and application thereof
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The invention relates to the fields of natural medicines and medicinal chemistry, and relates to a preparation method of a series of chromone 3-position nitric oxide donor derivatives with antitumor activity and a new application of the chromone 3-position nitric oxide donor derivatives in preparation of antitumor medicines. The chromone 3-position nitric oxide donor derivative and the pharmaceutically acceptable salt thereof are shown as a general formula I in the specification. Wherein R and R1 are described in the claims and the specification.
- -
-
Paragraph 0024-0026
(2021/05/05)
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- Chromone 3-piperazine linked furazan derivative as well as preparation method and application thereof
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The invention relates to the fields of natural medicines and medicinal chemistry, and relates to a preparation method of a series of chromone 3-piperazine linked furazan derivatives with antitumor activity and a new application of the chromone 3-piperazine linked furazan derivatives in preparation of antitumor medicines. The chromone 3-piperazine linked furazan derivative and the pharmaceutically acceptable salt thereof disclosed by the invention are as shown in a general formula I in the specification. Wherein R is described in the claims and the specification.
- -
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Paragraph 0021-0023
(2021/05/05)
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- Chromone 2-position nitric oxide donor derivative as well as preparation method and application thereof
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The invention relates to the fields of natural medicines and medicinal chemistry, and relates to a preparation method of a series of chromone 2-position nitric oxide donor derivatives with antitumor activity and a new application of the chromone 2-position nitric oxide donor derivatives in preparation of antitumor medicines. The chromone 2-position nitric oxide donor derivative and the pharmaceutically acceptable salt thereof are shown as a general formula I in the specification. Wherein R and R1 are described in the claims and the specification.
- -
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Paragraph 0021-0023
(2021/05/05)
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- Chromone 2-piperazine linked furazan derivative as well as preparation method and application thereof
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The invention relates to the fields of natural medicines and medicinal chemistry, and relates to a preparation method of a series of chromone 2-piperazine linked furazan derivatives with antitumor activity and a new application of the chromone 2-piperazine linked furazan derivatives in preparation of antitumor medicines. The chromone 2-piperazine linked furazan derivative and the pharmaceutically acceptable salt thereof disclosed by the invention are as shown in a general formula I in the specification. Wherein R is described in the claims and the specification.
- -
-
Paragraph 0014; 0021-0023
(2021/05/05)
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- Novel chromenyl-based 2-iminothiazolidin-4-one derivatives as tubulin polymerization inhibitors: Design, synthesis, biological evaluation and molecular modelling studies
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Here-in, we present molecular design, chemical synthesis and evaluation of novel chromenyl-based 2-iminothiazolidin-4-one derivatives as tubulin polymerization inhibitors. The newly synthesized compounds were evaluated for their in vitro cytotoxicities against A549 (lung cancer), MDA-MB-231 and BT-471 (breast cancer), HepG2 (liver cancer) and HCT-116 (colon cancer) cell lines by MTT assay. Among the synthesized compounds, compound 12b showed excellent anticancer activity on MDA-MB-231 cell line with IC50 value of 0.95 ± 1.88 μM and was verified to be safe in normal human bronchial epithelial cells (Beas-2B). Apoptosis induced by the lead 12b was observed using morphological observations, AO/EB and DAPI staining procedures. Further, dose-dependent increase in the depolarization of mitochondrial membrane was also observed through JC-1 staining. Annexin V-FITC/PI assay confirmed that 12b induced early apoptosis. Additionally, cell cycle analysis indicated that the MDA-MB-231 cells were arrested at sub-G2/M phase and also inhibited tubulin polymerization with IC50 value of 3.54 ± 0.2 μM. Molecular docking simulations were employed to identify the important binding modes responsible for the tubulin inhibitory activity, thus supporting their effective anticancer potential.
- Bathini, Nagendra Babu,Godugu, Chandraiah,Guggilapu, Sravanthi Devi,Kadagathur, Manasa,Pooladanda, Venkatesh,Sigalapalli, Dilep Kumar,Tangellamudi, Neelima D.,Uppu, Jaya Lakshmi
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- NHC-Catalyzed Cascade Reaction between β-Methyl Enals and Dienones for Quick Construction of Complex Multicyclic Lactones
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A NHC-promoted cascade reaction between β-methyl enal and dienone is developed for quick access to multicyclic lactone molecules bearing quaternary chiral carbon centers. Our study constitutes the first 1,6-addition of the acylazolium vinyl enolate γ-carbon via NHC catalysis and provides rapid access to complex lactone molecules that are otherwise difficult to prepare. The structurally sophisticated lactone products bearing up to four fused ring structures are afforded in up to quantitative yields with good to excellent enantioselectivities.
- Sun, Jun,Xu, Jun,Nie, Guihua,Jin, Zhichao,Chi, Yonggui Robin
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supporting information
p. 2595 - 2599
(2020/03/30)
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- Novel p-functionalized chromen-4-on-3-yl chalcones bearing astonishing boronic acid moiety as MDM2 inhibitor: Synthesis, cytotoxic evaluation and simulation studies
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Background: Novel 4-[3-(6/7/8-Substituted 4-Oxo-4H-chromen-3-yl)acryloyl]phenyl-boronic acid derivatives (5a-h) as well as other 6/7/8-substituted-3-(3-oxo-3-(4-substituted-phenyl)prop-1-enyl)-4H-chromen-4-one derivatives (3a-u) have been designed as p53-MDM2 pathway inhibitors and reported to possess significant cytotoxic properties against several cancer cell lines. Objectives: The current project aims to frame the structure-anticancer activity relationship of chromen-4-on-3-yl chalcones (3a-u/5a-h). In addition, docking studies were performed on these chromeno-chalcones in order to have an insight into their interaction possibilities with MDM2 pro-tein. Methods: Twenty-nine chromen-4-on-3-yl chalcone derivatives (3a-u/5a-h) were prepared by utilizing silica supported-HClO4 (green route with magnificent yield) and tested against four cancer cell lines (HCT116, MCF-7, THP-1, NCIH322). Results: Among the series 3a-u, compound 3b exhibited the highest anticancer activity (with IC50 values ranging from 8.6 to 28.4 μM) overall against tested cancer cell lines. Interestingly, para-Boronic acid derivative (5b) showed selective inhibition against colon cancer cell line, HCT-116 with an IC50 value of 2.35 μM. Besides the emblematic hydrophobic interactions of MDM2 inhibi-tors, derivative 5b was found to exhibit extra hydrogen bonding with GLN59 and GLN72 residues of MDM2 in molecular dynamics (MD) simulation. All the compounds were virtually nontoxic against normal fibroblast cells. Conclusion: Novel compounds were obtained with good anticancer activity especially 6-Chlorochromen-4-one substituted boronic acid derivative 5b. The molecular docking study proposed good activity as a MDM-2 inhibitor suggesting hydrophobic as well as hydrogen bonding interactions with MDM2.
- Bhatia, Richa Kaur,Coutinho, Evans C.,Garg, Ruchika,Kancherla, Satyavathi,Kaur, Maninder,Madan, Jitender,Pissurlenkar, Raghuvir R. S.,Singh, Lakhwinder,Yadav, Manmohan
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p. 212 - 228
(2020/03/10)
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- Synthesis and biological evaluation of chromone-3-carboxamides
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The aim of our study was to synthesize novel chromone-3-carboxamides and to conduct biological evaluations in search for lead compounds for the treatment of a range of debilitating disease states. Corresponding 2-hydroxyacetophenones were subjected to Vilsmeier-Haack formylation to give chromone-3-carbaldehydes, which were subsequently oxidised to give chromone-3-carboxylic acids. Treatment of the carboxylic acids with thionyl chloride resulted in the in situ formation of the corresponding acid chlorides, which were reacted with various amines in the presence of triethylamine to give the corresponding novel chromone-3-carboxamides in good yields. Selected chromone derivatives were then evaluated for their anti-inflammatory, anti-tryponosomal and cytotoxic properties.
- Gordon, Allen T.,Ramaite, Isaiah D.I.,Mnyakeni-Moleele, Simon S.
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p. 148 - 160
(2021/01/20)
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- Antiproliferative chromone derivatives induce K562 cell death through endogenous and exogenous pathways
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A series of furoxan derivatives of chromone were prepared. The antiproliferative activities were tested against five cancer cell lines HepG2, MCF-7, HCT-116, B16, and K562, and two normal human cell lines L-02 and PBMCs. Among them, compound 15a exhibited the most potent antiproliferative activity. It was also found 15a produced more than 8 μM of NO at the peak time of 45 min by Griess assay. Generally, antiproliferative activity is positively related to NO release to some extent. Further in-depth studies on apoptosis-related mechanisms showed that 15a caused S-phase cell cycle arrest in a concentration-dependent manner and induced apoptosis significantly through mitochondria-related pathways. Human apoptosis protein array assay also demonstrated 15a increased the expression levels of pro-apoptotic Bax, Bad, HtrA2 and Trail R2/DR5. The expression of catalase and cell cycle blocker claspin were similarly up-regulated. In balance, 15a induced K562 cells death through both endogenous and exogenous pathways.
- Cao, Hao,Hua, Huiming,Huang, Xiaofang,Jiao, Runwei,Li, Dahong,Li, Haonan,Li, Zhanlin,Liu, Weiwei,Xu, Fanxing,Zang, Linghe
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p. 759 - 772
(2020/04/01)
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- Chromone and donepezil hybrids as new multipotent cholinesterase and monoamine oxidase inhibitors for the potential treatment of Alzheimer's disease
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A series of chromone and donepezil hybrids were designed, synthesized, and evaluated as multipotent cholinesterase (ChE) and monoamine oxidase (MAO) inhibitors for the potential therapy of Alzheimer's disease (AD). In vitro studies showed that the great majority of these compounds exhibited potent inhibitory activity toward BuChE and AChE and clearly selective inhibition for hMAO-B. In particular, compound 5c presented the most balanced potential for ChE inhibition (BuChE: IC50 = 5.24 μM; AChE: IC50 = 0.37 μM) and hMAO-B selectivity (IC50 = 0.272 μM, SI = 247). Molecular modeling and kinetic studies suggested that 5c was a mixed-type inhibitor, binding simultaneously to peripheral and active sites of AChE. It was also a competitive inhibitor, which occupied the substrate and entrance cavities of MAO-B. Moreover, compound 5c could penetrate the blood-brain barrier (BBB) and showed low toxicity to rat pheochromocytoma (PC12) cells. Altogether, these results indicated that compound 5c might be a hopeful multitarget drug candidate with possible impact on Alzheimer's disease therapy.
- Huang, Ming,Jiang, Neng,Kong, Ling-Yi,Lan, Jin-Shuai,Wang, Xiao-Bing,Yin, Fu-Cheng
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p. 225 - 233
(2020/04/22)
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- One pot and metal-free approach to 3-(2-Hydroxybenzoyl)-1-aza-anthraquinones
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Herein, a direct strategy to synthesize 3-(2-hydroxybenzoyl)-1-aza-anthraquinones with excellent efficiency,mild conditions, and benign functional group compatibilitywas reported. Avariety of 3-formylchromone compounds were employed as compatible substrates and this protocol gave the 3-(2-hydroxybenzoyl)-1-aza-anthraquinone derivatives in good to excellent yields without inert gas and expensive transition metal catalysts. Some compounds displayed good anti-proliferative activities.
- Yuan, Jiaqi,He, Qian,Song, Shanshan,Zhang, Xiaofei,Miao, Zehong,Yang, Chunhao
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supporting information
(2019/08/30)
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- Synthesis and Antimicrobial Activity of (Z)-3-{[3-Oxobenzofuran-2(3H)-ylidene]methyl}-4H-chromen-4-one Derivatives
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A series of (Z)-3-{[3-oxobenzofuran-2(3H)-ylidene]methyl}-4H-chromen-4-one derivatives have been synthesized from 2-hydroxyl acetophenones by the Vilesmeier–Haack reaction, Claisen–Schmidt reaction and mercury(II) acetate/cupric bromide. All the synthesized compounds were characterized by IR, 1H and 13C NMR, and mass spectral data and elemental analysis. The products were tested for their in vitro antimicrobial activity.
- Pervaram,Ashok,Reddy,Sarasija,Rao
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p. 566 - 572
(2018/04/23)
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- Synthesis, characterization and antibacterial activity of nanocrystalline Ni(II)-6-methyl-4-oxo-4H-chromene-3-carbaldehyde complex
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The methyl substituted 3-formyl chromones was synthesized by Vilsmeier-Haack reaction. Nickel(II) complex was synthesized by refluxing the mixture of ligand solution taken into ethanol:acetic acid as 1:1 ratio and Ni(II) salt solution. The nature of bonding and geometry of the Ni(II) complex have been characterized from elemental analysis, FTIR, UV-visible spectral studies, thermal methods like TGA, the magnetic susceptibility, XRD, SEM, ESI-MS and molar conductance measurement, etc. Nickel(II) chloride is forming 1:2 (M:L) complex. The FTIR spectrum shows characteristic frequency band at 1614 cm-1 and 1695 cm-1, which belongs to carbonyl of pyron ring and neighboring aldehyde carbonyl in ligand respectively. The Ni(II)-ligand complex shows characteristic frequency of M-O- bonding in 545-466 cm-1 region. The electronic spectrum shows three absorption bands and confirmed complex has octahedral geometry. The formation of nanocrystalline complex and their bird feather like morphology was identified by powder XRD and SEM. Finally, NiO residue was obtained in thermogravimetric study of the complex. The ligand and its Ni(II) complex were screened for antimicrobial activities by the agar well diffusion technique.
- Kolhe,Jadhav,Takate,Aware,Athare
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p. 119 - 123
(2016/12/22)
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- A novel synthesis of chromone based unnatural α -amino acid derivatives
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An efficient method for the preparation of chromone based α -amino acid derivatives by alkylation of glycinate schiff base with 3-bromomethyl chromone as well as 2-bromomethyl chromone has been described. Using this method, 2-amino-3-(4-oxo-2-chromenyl)propanoic acid and 2-amino-3-(4-oxo-3-chromenyl)propanoic acid, two novel chromone-amino acid conjugates have been prepared. Furthermore, the separation of chromone amino acid enantiomers by chiral column chromatography was accomplished. Graphical Abstract?: Synopsis: An efficient method for the preparation of chromone based α -amino acid derivatives by alkylation of glycinate schiff base with 3-bromomethyl chromone as well as 2-bromomethyl chromone has been described. These conjugates can be considered as analogues of phenyl alanine where phenyl group has been replaced by chromone moiety.[Figure not available: see fulltext.].
- Kandula, Venu,Gudipati, Ramakrishna,Chatterjee, Anindita,Kaliyaperumala, Muralidaran,Yennam, Satyanarayana,Behera, Manoranjan
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p. 1233 - 1245
(2017/08/26)
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- Coumarin versus Chromone Monoamine Oxidase B Inhibitors: Quo Vadis?
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Because of the lack of significant disease-modifying drugs for neurodegenerative disorders, a pressing need for new chemical entities endowed with IMAO-B still exists. Within this framework, and for the first time, a study was performed to compare coumari
- Fonseca, André,Reis, Joana,Silva, Tiago,Matos, Maria Jo?o,Bagetta, Donatella,Ortuso, Francesco,Alcaro, Stefano,Uriarte, Eugenio,Borges, Fernanda
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supporting information
p. 7206 - 7212
(2017/09/07)
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- Direct construction of xanthene and benzophenone derivatives via Br?nsted acid controlled Diels-Alder reaction of 3-vinylchromones and arynes
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A Br?nsted acid controlled Diels-Alder reaction of 3-vinylchromones with arynes has been developed. By employing different kinds and amounts of acid, 9-aryl-9H-xanthen-9-ols or ortho-hydroxybenzophenones could be controllably furnished in good yields in an atom- and step-economic manner.
- Huang, Xu-Jiao,Tao, Yuan,Li, Yue-Kun,Wu, Xin-Yan,Sha, Feng
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supporting information
p. 8565 - 8577
(2016/12/09)
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- Design, synthesis and docking studies of novel thienopyrimidine derivatives bearing chromone moiety as mTOR/PI3Kα inhibitors
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Two series of thienopyrimidine derivatives (10a-k, 16a-j) bearing chromone moiety were designed and synthesized. All the compounds were evaluated for inhibitory activity against mTOR kinase at a concentration of 10uM. Four selected compounds were further evaluated for the IC50 values against mTOR kinase, PI3Kα kinase and two cancer cell lines. Some of the target compounds exhibited moderate to excellent mTOR/PI3Kα kinase inhibitory activity and cytotoxicity. The most promising compound 16i showed good inhibitory activity against mTOR/PI3Kα kinase and good antitumor potency for H460 and PC-3 cell lines with IC50 values of 0.16 ± 0.03 μM, 2.35 ± 0.19 μM, 1.20 ± 0.23 μM and 0.85 ± 0.04 μM, which were 8.6, >5, 7.9 and 19.1 times more active than compound I (1.37 ± 0.07 μM, >10 μM, 9.52 ± 0.29 μM, 16.27 ± 0.54 μM), respectively. Structure-activity relationships (SARs) and docking studies indicated that the chromone moiety is necessary for the potent antitumor activity and cytotoxicity of these compounds. Substitution of the chromone moiety at the 6-position has a significant impact to the inhibitory activity, in particular a carboxylic acid group, produced the best potency.
- Zhu, Wufu,Chen, Chen,Sun, Chengyu,Xu, Shan,Wu, Chunjiang,Lei, Fei,Xia, Hui,Tu, Qidong,Zheng, Pengwu
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- Thiazolidine-2,4-diones derivatives as PPAR-γ agonists: Synthesis, molecular docking, in vitro and in vivo antidiabetic activity with hepatotoxicity risk evaluation and effect on PPAR-γ gene expression
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A library of conjugates of chromones and 2,4-thiazolidinedione has been synthesized by Knoevenagel condensation followed by reduction using hydrogen gas and Pd/C as a catalyst. Compounds 5c and 5e were most effective in lowering the blood glucose level comparable to standard drug pioglitazone. Compound 5e exhibited potent PPAR-γ transactivation of 48.72% in comparison to pioglitazone (62.48%). All the molecules showed good glide score against the PPAR-γ target in molecular docking study. PPAR-γ gene expression was significantly increased by compound 5e (2.56-fold) in comparison to standard drug pioglitazone. Compounds 5e and 5c did not cause any damage to the liver and may be considered as promising candidates for the development of new antidiabetic agents.
- Nazreen, Syed,Alam, Mohammad Sarwar,Hamid, Hinna,Yar, Mohammad Shahar,Dhulap, Abhijeet,Alam, Perwez,Pasha,Bano, Sameena,Alam, Mohammad Mahboob,Haider, Saqlain,Kharbanda, Chetna,Ali, Yakub,Pillai
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p. 3034 - 3042
(2014/06/24)
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- Design and syntheses of novel N′-((4-oxo-4H-chromen-3-yl)methylene) benzohydrazide as inhibitors of cyanobacterial fructose-1,6-/sedoheptulose-1,7- bisphosphatase
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Cyanobacterial fructose-1,6-/sedoheptulose-1,7-bisphoshatase (Cy-FBP/SBPase) is an important target enzyme for finding inhibitors to solve harmful algal bloom (HAB). In this study, as potential inhibitors of Cy-FBP/SBPase, a series of novel chromone-connecting benzohydrazone compounds (Novel N′-((4-oxo-4H-chromen-3-yl)methylene)benzohydrazide) were designed and synthesized. Their inhibitory activities against Cy-FBP/SBPase were further examined in vitro. Some of these compounds, such as f6-f8, f11, f12 and f16, exhibit higher inhibitory activities (IC50 = 11.2-16.1 μM), especially, the compound f7 was identified as the most potent inhibitor with IC50 value of 11.2 μM. The probable binding-mode of compound f7 was further analyzed carefully by molecular docking methods. These results indicate that compound f7 could be used as a lead compound for further optimization and might have potential to be developed as a new algicide.
- Tu, Qi-Dong,Li, Ding,Sun, Yao,Han, Xin-Ya,Yi, Fan,Sha, Yibamu,Ren, Yan-Liang,Ding, Ming-Wu,Feng, Ling-Ling,Wan, Jian
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p. 2826 - 2831
(2013/06/27)
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- 3-Formylchromone based topoisomerase IIα inhibitors: Discovery of potent leads
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Substituted 3-formylchromones were synthesized and evaluated as inhibitors of the human DNA topoisomerase IIα (hTopo-IIα) enzyme. The results of the decatenation, relaxation and DNA intercalation assays revealed that the compounds (11b, 12a, 12b, 12d, 12e, 13a and 13b) exhibited potent inhibitory activity against the hTopo-IIα enzyme, and are nonintercalating agents. These compounds also possess significant in vitro cytotoxicity (LC50 ranges from 0.5-8.6 μM) against prostate (PC-3) cancerous cell line as seen in comparison to the standard drug etoposide. To further probe the plausible mode of action of 3-formylchromone derivatives, molecular docking studies have also been carried out, which showed that the compounds under investigation fitted well in the ATP binding pocket of hTopo-IIα enzyme with good docking scores and form nonbonding interactions with the crucial residues of the catalytic site. The Royal Society of Chemistry.
- Singh, Satyajit,Baviskar, Ashish Triambak,Jain, Vaibhav,Mishra, Nidhi,Chand Banerjee, Uttam,Bharatam, Prasad V.,Tikoo, Kulbhushan,Singh Ishar, Mohan Paul
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p. 1257 - 1266
(2013/09/12)
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- Novel benzofuran-chromone and -coumarin derivatives: Synthesis and biological activity in K562 human leukemia cells
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Not widely distributed in nature, aurones, (Z)-2-benzylidene-benzofuran- 3(2H)-ones, are one of the less common and lesser-known representatives of a flavonoid subclass. Nevertheless, they exhibit a strong and broad variety of biological activities. We have combined the benzofuranone part of a classical aurone with either a chromone or a coumarin scaffold which proved to feature interesting biological activities including antimicrobial, antiviral, anticancer, anti-inflammatory and antioxidant properties. Herein we present a series of 26 novel benzofuran derivatives with the first biological results in K562 human leukemia cells showing that compounds 21b, 29b and 29c are able to induce around 24% apoptosis.
- Zwergel, Clemens,Valente, Sergio,Salvato, Angela,Xu, Zhanjie,Talhi, Oualid,Mai, Antonello,Silva, Artur,Altucci, Lucia,Kirsch, Gilbert
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supporting information
p. 1571 - 1579
(2013/12/04)
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- One-pot syntheses of novel pyrazole-containing bisphosphonate esters at room temperature
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An efficient general synthetic approach has been developed to synthesize pyrazole-containing bisphosphonate (N-BPs) esters from chromenone derivatives via a sequential two-step reaction in one pot at ambient temperature in good to excellent yields. This protocol provides a new convenient method to prepare lipophilic bisphosphonate precursors with potential activities. The Royal Society of Chemistry 2012.
- Xiang, Haoyue,Qi, Xueyu,Xie, Yuyuan,Xu, Guangyu,Yang, Chunhao
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supporting information
p. 7730 - 7738
(2013/04/23)
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- Synthesis, structure-activity relationship of novel substituted 4H-chromen-1,2,3,4-tetrahydropyrimidine-5-carboxylates as potential anti-mycobacterial and anticancer agents
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Series of 4H-chromen-1,2,3,4-tetrahydropyrimidine-5-carboxylate derivatives 7a-7zb, 8a-8d and 9a-9d were synthesized and screened for their in vitro anti-mycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB) and cytotoxicity against three human cancer cell lines including A549, SK-N-SH and HeLa. The results indicate that six compounds are more potent and 7za is most effective anti-mycobacterial derivative compared to the standard drugs Ethambutol and Ciprofloxacin. However, 12 compounds exhibited cytotoxicity against human neuroblastoma cell line; amongst them the compound 7v is most effective compared to the standard drug Doxorubicin. This is the first report assigning in vitro anti-mycobacterial, anticancer and structure-activity relationship for this new class of 4H-chromen-1,2,3,4-tetrahydropyrimidine-5- carboxylates.
- China Raju,Nageswara Rao,Suman,Yogeeswari,Sriram,Shaik, Thokhir Basha,Kalivendi, Shasi Vardhan
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p. 2855 - 2859
(2011/06/24)
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- Synthesis of 3-[3-(benzothiazol-2-yl)-4-oxo-thiazolidin-2-yl]chromones as Antifungal agents
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Antifungal activities associated with chromones and thiazolidones prompted us to synthesize 3-[3-(benzothiazol-2-yl)-4-oxo-thiazolidin-2-yl]chromones through the intermediacy of Schiff bases. Structures of new compounds have been assigned by the interpretation of their IR and PMR spectral data and are supported by elemental analysis. One of the Schiff base adduct has shown high antifungal activity (90.93 % inhibition of growth) against Aspergillus niger i.e., the fungus responsible for food poisoning and aspergillosis. It is worth mentioning as the isolation and purification of Schiff bases was not easy due to 1,4-adduct formation. Hence, a one pot synthesis of title compounds was designed by refluxing a mixture of 3-formylchromone, 2-aminobenzothiazole and thioglycollic acid (TGA) in benzene in presence of zinc chloride instead of reacting Schiff base with thioglycollic acid.
- Sharma, Vinay Prabha,Kumar, Praveen,Sharma, Meenakshi
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p. 4616 - 4620
(2012/02/04)
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- Synthesis and characterization and anti-inflammatory and antibacterial evaluation of 3-arylidene-7-methoxychroman-4-ones
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3-Arylidene-7-methoxychroman-4-ones 3a-k have been prepared from 7-methoxy-chroman-4-one 1 and heterocyclic aldehydes 2 and have been evaluated for anti-inflammatory and antibacterial activities. All of them have registered moderate anti-inflammatory and antibacterial activities.
- Shankar,Gandhidasan,Venkataraman
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experimental part
p. 1202 - 1207
(2011/10/13)
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- Synthesis and reactivity of 3-(1-hydroxy-3-buten-1-yl)chromone
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Zn-induced allylation of chromone-3-carbaldehyde 1 produces 3-(1-hydroxy-3-butene-1-yl)chromone 2, which gives back 1 on treatment with formalin under acidic conditions, and reacts differently towards nitrogenous nucleophiles.
- Karmakar, Partha,Ghosh, Tarun,Chakrabarty, Debasish,Maiti, Sourav,Bandyopadhyay, Chandrakanta
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experimental part
p. 208 - 211
(2009/08/07)
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- Microwave-induced synthesis and regio- and stereoselective epoxidation of 3-styrylchromones
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The microwave-assisted solvent-free synthesis of (E)-3-styrylchromones from 3-formylchromones and phenylmalonic acid on sodium acetate support has been developed; the method affords the styryl derivatives in moderate to good yields and with complete diastereoselectivity. Protocols for the highly regioselective epoxidation of (E)- and (Z)-3-styrylchromones have been elaborated. Treatment of the alkenes with dimethyldioxirane led to the exclusive formation of 3-(3-aryloxiran-2-yl)chromones with complete diastereoselectivity, whereas treatment with hydrogen peroxide under alkaline conditions afforded the corresponding 2,3-epoxy-3-styrylchromanones as the only products. Epoxidation performed in the presence of chiral, nonracemic cinchona-alkaloid-based quaternary ammonium salts allowed the synthesis of enantiomerically enriched 2,3-epoxy-3-styrylchromanones, but with only moderate ee values. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Patonay, Tamas,Kiss-Szikszai, Attila,Silva, Vera M. L.,Silva, Artur M. S.,Pinto, Diana C. G. A.,Cavaleiro, Jose A. S.,Jeko, Jozsef
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body text
p. 1937 - 1946
(2009/04/04)
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- Synthesis and insecticidal activity of chromanone and chromone analogues of diacylhydrazines
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Diacylhydrazine derivatives have been identified as one of the most important insect growth regulators. A variety of diacylhydrazine derivatives were designed and synthesized in recent years due to their unique action mechanism, simple structure, and environmental benign character. This paper describes the molecular design, synthesis, and insecticidal activities of a series of chromanone and chromone analogues of diacylhydrazine derivatives. The preliminary bioassay showed that some of the chromanone analogues exhibited good insecticidal activity against Mythima separata at the dosage of 500 mg L-1. The present work demonstrated that replacement of the chroman ring of ANS-118, a commercial insecticide, with chromanone moiety could result in new compounds with high potent insecticidal activity.
- Zhao, Pei-Liang,Li, Jing,Yang, Guang-Fu
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p. 1888 - 1895
(2007/10/03)
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- Ceric ammonium nitrate catalyzed efficient and chemoselective method for protection and deprotection of 4-oxo-4H-1-benzopyran-3-carbaldehydes
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A chemoselective, solvent-free, mild and efficient method for the synthesis of acylals and their deprotection to 4-oxo-4H-1-benzopyran-3-carbaldehydes catalyzed by ceric ammonium nitrate (CAN) are carried out in good yields and all compounds 2a-h are characterized by IR, 1H NMR and 13C NMR spectral data.
- Shindalkar,Madje,Hangarge,Shingare
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p. 2409 - 2411
(2007/10/03)
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- Synthesis of 3-(3-alkyl-5-thioxo-1H-4,5-dihydro-1,2,4-triazol-4-yl) aminocarbonylchromones
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A series of 3-(3-alkyl-5-thioxo-1H-4,5-dihydro-1,2,4-triazol-4-yl) aminocarbonylchromones has been prepared by oxidation of 3-formylchromone with Jones' reagent followed by reaction with 3-alkyl-4-amino-4,5-dihydro-1,2,4- triazole-5(1H)-thione in the presence of POCl3. The structures of the compounds were confirmed by IR, LC-MS, and 1H NMR spectra and elemental analyses.
- Cao, Linghua,Zhang, Lin,Cui, Pengyuan
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p. 635 - 640
(2007/10/03)
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- Diels-Alder reactions of chromone-3-carboxaldehydes with ortho-benzoquinodimethane. New synthesis of benzo[b]xanthones
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An efficient new route to the benzo[b]xanthone system has been developed and applied to the synthesis of several new derivatives. The cycloaddition reactions of chromone-3-carboxaldehydes 12, reacting as dienophiles, with ortho-benzoquinodimethane 7 gave a diastereomeric mixture of cycloadducts 8 and 9. The formation of these compounds results from the Diels-Alder reactions of 12 and 7 followed by the in situ deformylation. The oxidation of adducts 8 and 9 with dimethyl sulfoxide in the presence of iodine gave the novel benzo[b]xanthones 11 in good yields.
- Sandulache, Angela,Silva, Artur M.S,Cavaleiro, José A.S
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p. 105 - 114
(2007/10/03)
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- 3-Formylchromones
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Novel 3-formylchromone derivatives are disclosed, substituted on the 5,6,7, or 8 positions by one or more of the following substituents: halogen, hydroxy, lower alkyl, lower alkoxy, lower acyl, lower acyloxy, or methylenedioxy. The corresponding 3-acetal or 3-hydrazone derivatives of the carboxaldehyde group are also disclosed. These compounds, and pharmaceutical compositions containing these compounds are useful for the treatment of allergic conditions and for the treatment of hyperacidity.
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- Substituted-3-formylchromone derivatives
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Novel 3-formylchromone derivatives are disclosed, substituted on the 5,6,7, or 8 positions by one or more of the following substituents: halogen, hydroxy, lower alkyl, lower alkoxy, lower acyl, lower acyloxy, or methylenedioxy. The corresponding 3-acetal or 3-hydrazone derivatives of the carboxaldehyde group are also disclosed. These compoounds, and pharmaceutical compositions containing these compounds are useful for the treatment of allergic conditions and for the treatment of hyperacidity.
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- Chromonealdehyde compounds and process for the production thereof
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There are provided compounds of the general formula SPC1 Wherein R is a hydroxy, alkyl, acyloxy, halogen, nitro, substituted or unsubstituted amino, alkoxy, carboxy or a group derived from a carboxy group and m is 0, 1 or 2 except where m is 2, the two R groups are both hydroxy groups. The present invention is also concerned with a process for preparing the chromonealdehyde compounds. The chromonealdehyde compounds are characterized by antiallergic properties and are therefore useful as prophylactic and therapeutic agents for allergic asthma, allergic dermatitis and other allergic diseases and also are valuable as intermediates for the synthesis of other pharmaceutical compounds having the chromone nucleus.
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