- Molecular docking and synthesis of caffeic acid analogous and its anti-inflammatory, analgesic and ulcerogenic studies
-
A series of caffeic acid (CA) derivatives 7a-j were synthesized via etherification and coupling action and their chemical structures were elucidated spectroscopically. Motivated by the various biological activities displayed by CA derivatives such as anti-inflammatory, antiviral, anticancer and antioxidant and also based on its extensively consumption in the human diet. In the present work, the newly synthesized compounds 7a-j were evaluated for anti-inflammatory and analgesic action and most of them exerted comparable activity to the reference compound celecoxib. Further, ulcer indexes for the most active compounds were calculated and most of them showed less ulcerogenic effect than the reference drug. Among the title series 7a-j, compounds 7f and 7g with electron withdrawing bromo and chloro group respectively, at the para position of the phenoxy ring was showed good activity compared to all other compounds. Interestingly, the COX-I/COX-II activity ratio of potent compounds 7f and7g showed an almost equal inhibitory effect on both isoenzymes. Further, molecular docking studies have been performed for the potent compounds which showed statistically significant result.
- Al-Ostoot, Fares Hezam,Ara Khanum, Shaukath,Grisha, S.,Mohammed, Yasser Hussein Eissa,Vivek, H. K.,Zabiulla
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- Synthesis and characterization of biologically important quinoline incorporated triazole derivatives
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Triazoles are well recognized in literature for their significant biologically active heterocyclic compounds. Also the quinoline nucleus found in several natural products shows a varied biological activity. Keeping in the view of these observations, a novel series of 6/7/8-substtuted-2-[(5-((4-chlorophenoxy)methyl)-4H-1,2,4-triazol-3-yl)thio]quinoline-3-carbaldehydes and 6/7/8-substituted-2-[(5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio]quinoline-carbaldehydes were synthesized by the condensation of 5-(4-chloro phenoxy methyl)-2,4-dihydro-1,2,4-triazole-3-thiones and 5-(pyridin-3-yl)-4H-1,2,4-triazole-3-thiols with 6/7/8-substituted-2-chloro quinoline-3-carbaldehydes. The new series were established by Mass, NMR and IR spectroscopy and were also screened for their antimicrobial activities. A few of the novel compounds exhibited tremendous bioactivities compared to that of normal drug.
- D'Souza, Vineetha Telma,Nayak, Janardhana,D'Mello, Desmond Edward,Dayananda
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- Expedient discovery for novel antifungal leads: 1,3,4-Oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment
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Developing novel fungicide candidates are intensively promoted by the rapid emergences of resistant fungi that outbreak on agricultural production. Aiming to discovery novel antifungal leads, a series of 1,3,4-oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment were constructed for evaluating their inhibition effects against phytopathogenic fungi in vitro and in vivo. Systematically structural optimizations generated the bioactive molecule I32 that was identified as a promising inhibitor against Rhizoctonia solani with the in vivo preventative effect of 58.63% at 200 μg/mL. The observations that were captured by scanning electron microscopy and transmission electron microscopy demonstrated that the bioactive molecule I32 could induce the sprawling growth of hyphae, the local shrinkage and rupture on hyphal surfaces, the extreme swelling of vacuoles, the striking distortions on cell walls, and the reduction of mitochondria numbers. The above results provided an indispensable complement for the discovery of antifungal lead bearing a quinazolin-4(3H)-one and 1,3,4-oxadiazole fragment.
- Chai, Jianqi,Chen, Min,Jin, Fei,Kong, Xiangyi,Wang, Xiaobin,Xue, Wei,Yang, Chunlong
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-
- N-Amino-1,8-Naphthalimide is a Regenerated Protecting Group for Selective Synthesis of Mono-N-Substituted Hydrazines and Hydrazides
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A new route to synthesis of various mono-N-substituted hydrazines and hydrazides by involving in a new C?N bond formation by using N-amino-1,8-naphthalimide as a regenerated precursor was invented. Aniline and phenylhydrazines are reproduced upon reacting these individually with 1,8-naphthalic anhydride followed by hydrazinolysis. The practicality and simplicity of this C?N dihalo alkanes; developed a synthon for bond formation protocol was exemplified to various hydrazines and hydrazides. N-amino-1,8-naphthalimide is suitable synthon for transformation for selective formation of mono-substituted hydrazine and hydrazide derivatives. Those are selective mono-amidation of hydrazine with acid halides; mono-N-substituted hydrazones from aldehydes; synthesis of N-aminoazacycloalkanes from acetohydrazide scaffold and inserted to hydroxy derivatives; distinct synthesis of N,N-dibenzylhydrazines and N-benzylhydrazines from benzyl halides; synthesis of N-amino-amino acids from α-halo esters. Ecofriendly reagent N-amino-1,8-naphthalimide was regenerated with good yields by the hydrazinolysis in all procedures.
- Manoj Kumar, Mesram,Venkataramana, Parikibanda,Yadagiri Swamy, Parikibanda,Chityala, Yadaiah
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supporting information
p. 17713 - 17721
(2021/11/10)
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- Identification of a Novel Oxadiazole Inhibitor of Mammalian Target of Rapamycin
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We performed a biochemical screen against mTOR using in-house small molecule library. Two novel, structurally distinct hits were identified. Among them, a novel oxadiazole scaffold compound (2) suppressed the phosphorylation of both S6K1 and Akt1 in HeLa cells. Docking study suggested that 2 is ATP-competitive and shows a pi-pi interaction with Trp2239 and hydrogen bonds with Trp2239 and Thr2245. Through derivatization, a slightly more potent analogue (2a) was identified with IC50 of 9.6 μM. Our study provides a starting point for discovery of novel potent mTOR inhibitors.
- Lim, Sunwoo,Lee, Hyomin,Kim, Euijung,Hur, Wooyoung
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p. 296 - 303
(2020/02/04)
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- Synthesis and Insecticidal Evaluation of Novel N-pyridylpyrazole Derivatives Containing Diacylhydrazine/1,3,4-Oxadiazole Moieties
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Two series of novel N-pyridylpyrazole derivatives containing diacylhydrazine/1,3,4-oxadiazole moieties were designed and synthesized based on the structure of chlorantraniliprole and characterized via 1H-NMR, 13C-NMR, IR, MS, and elemental analysis. The preliminary bioassay indicated that some of the title compounds I and II exhibited larvicidal activities against Mythimna separata with 90–100% death rates at 500?mg/L. The further test showed that these compounds had weak insecticidal activity against Mythimna separata and Plutella xylostella at 200?mg/L and might be not suitable as insecticide lead compound for further optimization.
- Wang, Wei,Zheng, Xiao-Rui,Huang, Xiao-Ying,Mao, Ming-Zhen,Liu, Kang-Yun,Xue, Chao,Wang, Lie-Ping,Ning, Bin-Ke
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p. 1330 - 1336
(2019/01/30)
-
- Synthesis and biological evaluations of some new oxadiazole–piperidine hybrid derivatives as antioxidant agents
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A series of some new 1,3,4-oxadiazole-2-thiol derivatives (6a-h) containing cyclic secondary amine such as piperidine ring was expeditiously synthesized by alkylation of 1,3,4-oxadiazol-2-thiol derivatives with chloroethyl piperidine hydrochloride. The 1,3,4-oxadiazole-2-thiols were effectively synthesized by cyclization reaction of acid hydrazide derivatives with carbon disulfide. The target compounds 6a-h were preliminarily screened for in vitro antioxidant activities using various in vitro antioxidant assays including 2,2′-diphenyl-1-picrylhydrazyl, nitric oxide, and hydrogen peroxide methods. The results showed that the compounds exhibited promising antioxidant property in the three methods at 50, 75, and 100 μM. Among the tested compounds, the compounds 6a and 6b having chloro substituent in the benzene ring displayed greater radical scavenging activity.
- Al-Ghorbani, Mohammed M. Abdullah
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p. 379 - 384
(2018/09/29)
-
- Synthesis and luminescence properties of novel 8-hydroxyquinoline derivatives and their Eu(III) complexes
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Six novel 8-hydroxyquinoline derivatives were synthesized using 2-methyl-8-hydroxyquinoline and para-substituted phenol as the main starting materials, and were characterized by 1H nuclear magnetic resonance (NMR), mass spectrometry (MS), ultraviolet (UV) light analysis and infra-red (IR) light analysis. Their complexes with Eu(III) were also prepared and characterized by elemental analysis, molar conductivity, UV light analysis, IR light analysis, and thermogravimetric–differential thermal analysis (TG–DTA). The results showed that the ligand coordinated well with Eu(III) ions and had excellent thermal stability. The structure of the target complex was EuY1–6(NO3)3.2H2O. The luminescence properties of the target complexes were investigated, the results indicated that all target complexes had favorable luminescence properties and that the introduction of an electron-donating group could enhance the luminescence intensity of the corresponding complexes, but the addition of an electron-withdrawing group had the opposite effect. Among all the target complexes, the methoxy-substituted complex (–OCH3) had the highest fluorescence intensity and the nitro-substituted complex (–NO2) had the weakest fluorescence intensity. The results showed that 8-hydroxyquinoline derivatives had good energy transfer efficiency for the Eu(III) ion. All the target complexes had a relatively high fluorescence quantum yield. The fluorescence quantum yield of the complex EuY3(NO3)3.2H2O was highest among all target complexes and was up to 0.628. Because of excellent luminescence properties and thermal stabilities of the Eu(III) complexes, they could be used as promising candidate luminescent materials.
- Wu, Yongqiang,Guo, Tiantong,Shu, Dehua,Zhang, Wu,Luan, Fangfei,Shi, Ling,Guo, Dongcai
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p. 855 - 862
(2018/07/13)
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- A 1, 2, 4 - triazole thioether derivative and its preparation and use
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The invention discloses a 1,2,4-triazolothio-ether derivative as well as a preparation and an application thereof. The compound with the concentration being 10 mu g/mL has better inhibition property on pythium ultimum trow, and the inhibition rate is up t
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-
Paragraph 0024; 0027-0028
(2018/05/30)
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- Synthesis and larvicidal activity of 1,3,4-oxadiazole derivatives containing a 3-chloropyridin-2-yl-1H-pyrazole scaffold
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Abstract: A new series of 1,3,4-oxadiazole derivatives with a 3-chloropyridin-2-yl-1H-pyrazole moiety was designed, synthesized, and characterized. The results of bioassay against Helicoverpa armigera and Plutella xylostella indicated that some of the synthesized compounds showed remarkable larvicidal activity. In particular, the LC50 values of the most active compounds against P. xylostella were 46.5, 23.9, and 13.9?mg/dm3, and against Helicoverpa armigera were 88.3 and 69.5?mg/dm3, the latter being slightly better than commercial chlorpyrifos (LC50 103.77?mg/dm3). Preliminary SAR was also discussed. Graphical abstract: [Figure not available: see fulltext.].
- Wang, Yanyan,Lu, Xiumian,Shi, Jun,Xu, Jiahong,Wang, Fenghua,Yang, Xiao,Yu, Gang,Liu, Zhiqian,Li, Chuanhui,Dai, Ali,Zhao, Yonghui,Wu, Jian
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p. 611 - 623
(2018/01/17)
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- Tirfluoromethylpyridine oxadiazoles (ether)derivative and application thereof
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The invention discloses an application of a tirfluoromethylpyridine oxadiazole (ether)derivative in a pesticide. A structure is shown as a general formula I, a compound shown in the general formula Ihas good insecticidal activity, and can be used for controlling insects such as diamondback moth and armyworm. The compound has excellent control effect for insects such as diamondback moth and armyworm, and also has control effect for the insects having resistance to the traditional pesticides, in addition, introduction of fluorine-containing groups such as tirfluoromethylpyridine and oxadiazoleas well as heterocyclic ring can enhance a rate for forming hydrogen bond effect between a compound and a target, and the activity of the compound is increased.
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-
Paragraph 0095; 0096; 0100; 0101
(2018/07/30)
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- Synthesis, Nematicidal Activity, and 3D-QSAR of Novel 1,3,4-Oxadiazole/ Thiadiazole Thioether Derivatives
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Forty one novel 1,3,4-oxadiazole/thiadiazole thioether derivatives containing phenoxy moiety were designed and synthesized. Bioassay demonstrated that some of them showed remarkable activities against Tylenchulus semipenetrans in vitro and in vivo. Compounds 20, 21, 35 and 39 showed excellent lethal activities after treatment for 48?h in vitro, with LC50 values of 13.4?±?1.8, 11.7?±?2.5, 13.7?±?2.4 and 13.3?±?1.1?mg·L–1, respectively, which were obviously superior to fosthiazate (49.1?±?2.8?mg·L–1) and avermectin (26.6?±?2.3?mg·L–1). Compound 21 can effectively control the citrus nematode disease caused by T. semipenetrans at 200?mg·L–1 in vivo with (68?±?3)% inhibitory effect, which was even better than that of avermectin ((63?±?2)%). The CoMFA and CoMSIA models of three-dimensional quantitative structure-activity relationships (3D-QSARs) were established. The compound 33 was designed based on the 3D-QSAR models with more vigorous nematicidal activities in vitro (LC50?=?9.8?±?1.4?mg·L–1) and in vivo ((70?±?5)%). These results demonstrated that compound 33 can be considered as a potential nematicide.
- Chen, Jixiang,Gan, Xiuhai,Yi, Chongfen,Wang, Shaobo,Yang, Yuyuan,He, Fangcheng,Hu, Deyu,Song, Baoan
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p. 939 - 944
(2018/09/22)
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- Synthesis and antibacterial evaluation of new sulfone derivatives containing 2-aroxymethyl-1,3,4-oxadiazole/thiadiazole moiety
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Sulfones are one of the most important classes of agricultural fungicides. To discover new lead compounds with high antibacterial activity, a series of new sulfone derivatives were designed and synthesized by introducing the aroxymethyl moiety into the scaffold of 1,3,4-oxadiazole/thiadiazole sulfones. Antibacterial activities against three phytopathogens (Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum, Xanthomonas axonopodis pv. citri.) were assayed in vitro. As compared to the control of commercial fungicides and some reported sulfone fungicides, seven compounds 5I-1-5I-7 exerted remarkably higher activities with EC50 values ranging from 0.45-1.86 μg/mL against X. oryzae and 1.97-20.15 μg/mL against R. solanacearum. Exhilaratingly, 5I-1, 5I-2 and 5I-4 displayed significant in vivo activity against X. oryzae with protective effect of 90.4%, 77.7%, and 81.1% at 200 μg/mL, respectively, much higher than that exhibited by Bismerthiazol (25.6%) and Thiadiazole-copper (32.0%). And the differential phytotoxicity of active derivatives was preliminarily checked. The results demonstrated that derivative of 2-aroxymethyl-1,3,4-oxadiazole/thiadiazole sulfone can serve as potential alternative bactericides for the management of plant bacterial diseases.
- Su, Shihu,Zhou, Xia,Liao, Guoping,Qi, Puying,Jin, Linhong
-
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- 2,5-substituent-1,3,4-oxadiazole (thiadiazole) thioether derivatives as well as preparation method and application thereof
-
The invention discloses 2,5-substituent-1,3,4-oxadiazole (thiadiazole) thioether derivatives as well as a preparation method and an application thereof. The 2,5-substituent-1,3,4-oxadiazole (thiadiazole) thioether derivatives have the general formula (I) shown in the following specification, wherein R1 represents as 4-chlorphenyl, 4-fluorophenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-cyano-3,5-difluorophenyl, 4-trifluoromethylphenyl, 4-trifluoromethoxyphenyl, 4-t-butylphenyl, 2-fluorophenyl and other substituents; R2 represents methyl, ethyl, 4-chlorobenzyl, 2,4-dichlorobenzyl, 4-trifluoromethoxy, benzyl, 4-fluorobenzyl, 4-chlorobenzyl and other substituents; X represents O or S. The compound can be used as a pesticide for killing crop nematode and inhibiting bacterial diseases of crops.
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-
Paragraph 0056
(2017/04/03)
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- Synthesis of acylhydrazines and, symmetrical and asymmetrical diacylhydrazines from carboxylic acid via the Vilsmeier reagent mediated process
-
(Chloromethylene)dimethylammonium chloride (Vilsmeier reagent) has been used as an efficient and convenient reagent for the one-pot synthesis of acylhydrazines and symmetrical and asymmetrical diacylhydrazines from carboxylic acids. This reaction proceeded smoothly under mild conditions and it is quite practical, since the starting carboxylic acids can be easily handled and stored. Cleanliness, simplicity of the method and good to excellent yield of products are other advantages of this method.
- Zarei, Maaroof,Nakhli, Maliheh Eslami
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p. 1909 - 1918
(2017/02/15)
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- One-pot synthesis of 1,3,4-thiadiazoles using Vilsmeier reagent as a versatile cyclodehydration agent
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A simple and efficient synthetic method for the one-pot synthesis of 1,3,4-thiadiazoles utilizing Vilsmeier reagent was developed. In this method carboxylic acids and hydrazine were converted to 1,3,4-thiadiazoles in the presence of Vilsmeier reagent and Lawesson's reagent. The influence of the thionation reagent, solvent, temperature and time, in this reaction was discussed. The developed methodology for 1,3,4-thiadiazole synthesis has the advantage of simplicity, ambient reaction conditions, easy purification and good to excellent yield of products.
- Zarei, Maaroof
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p. 1867 - 1872
(2017/03/11)
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- Synthesis of oxadiazole-morpholine derivatives and manifestation of the repressed CD31 Microvessel Density (MVD) as tumoral angiogenic parameters in Dalton's Lymphoma
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A series of oxadiazole derivatives possessing morpholine 6a-l were synthesized by nucleophilic substitution reaction of key intermediates [1,3,4]-oxadiazole-2-thiol derivatives 5a-l with 4-(2-chloroethyl) morpholine. Compounds 6a-l were evaluated for their in vitro and in vivo antitumor potential in Dalton's Lymphoma Ascites (DLA) tumor cells. Among 6a-l series, compound 6a with concentration ~8.5 μM have shown extensive cytotoxicity in vitro and 85% reduction in tumor volume in vivo, attributing an excellent anti-proliferative capability towards the cancer cells. Compound 6a has extensively inhibited the Microvessel Density (MVD) or tumoral neovasculature which was evident from the CD31 immuno staining and peritoneal H&E staining. The major reason for the antiproliferative activity of compound 6a was due to the repression of tumor vasculature.
- Al-Ghorbani, Mohammed,Vigneshwaran,Ranganatha, V. Lakshmi,Prabhakar,Khanum, Shaukath Ara
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p. 136 - 146
(2015/06/02)
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- Synthesis, Characterization and Properties of Novel Coumarin Derivatives and Their Europium Complexes
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Seven novel coumarin derivatives derived from salicylaldehyde and phenol were synthesized and characterized by 1H NMR and 13C NMR spectra, mass spectra, infrared spectra and elemental analysis. Their corresponding Eu(III) complexes having general formula EuL1-7(NO3)3·2H2O were successfully prepared and characterized by elemental analysis, EDTA titrimetric, molar conductivity, UV-Vis, FT-IR and thermal performance studies. The luminescence properties, fluorescence quantum yields and the electrochemical properties of the title complexes were investigated. The results showed that the title complexes exhibited characteristic emissions of europium ions and possessed relatively good fluorescence quantum yields. The luminescence intensity of the complex with bromine-substituted group is the strongest among all the title complexes. The introduction of electron-withdrawing groups can increase the luminescence properties and fluorescence quantum yields, decrease the HOMO and LUMO energy levels of the title europium complexes, but electron-withdrawing group conversely. And these title complexes may possibly be useful for studying in luminescent materials field.
- Yan, Dong,Li, Dong,Cheng, Guang,Yang, Zehui,Shi, Ling,Guo, Dongcai
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p. 849 - 859
(2015/08/24)
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- Synthesis, Structural Analysis, and Screening of Some Novel 5-Substituted Aryl/Aralkyl-1,3,4-Oxadiazol-2-Yl 4-(Morpholin-4-Ylsulfonyl)Benzyl Sulfides As Potential Antibacterial Agents
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A series of new 5-substituted aryl/aralkyl-1,3,4-oxadiazol-2-yl 4-(morpholin-4-ylsulfonyl)benzyl sulfides 6a-k were synthesized by converting multifarious aryl/aralkyl organic acids 1a-k successively into corresponding esters 2a-k, hydrazides 3a-k, and 5-substituted aryl/aralkyl-1,3,4-oxadiazole-2-thiols 4a-k. Finally, the target compounds, 6a-k were prepared by stirring 5-substituted-1,3,4-oxadiazole-2-thiols with 4-(4-(bromomethyl)phenylsulfonyl) morpholine (5) in the presence of N,N-dimethylformamide (DMF) and sodium hydride (NaH). The structures of the newly synthesized compounds were elucidated by spectroscopic techniques. In addition, the antibacterial activity of all the synthesized compounds was investigated in vitro against Gram-positive and Gram-negative bacteria by using ciprofloxacin as reference standard drug and the results showed that some of the tested compounds possessed good antibacterial activity.
- Aziz-Ur-Rehman,Gul, Samreen,Abbasi, Muhammad Athar,Nafeesa, Khadija,Akhtar, Muhammad Nadeem,Ahmad, Irshad,Afzal, Saira
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p. 1045 - 1055
(2015/08/04)
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- Synthesis and luminescence properties of pyrazolone derivatives and their terbium complexes
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Seven novel pyrazolone derivatives were synthesized and characterized by 1H NMR and 13C NMR spectra, mass spectra, infrared spectra and elemental analysis. Their terbium complexes were prepared and characterized by elemental analysis, EDTA titrimetric analysis, UV/vis spectra, infrared spectra and molar conductivity, as well as thermal analysis. The fluorescence properties and fluorescence quantum yields of the complexes were investigated at room temperature. The results indicated that pyrazolone derivatives had good energy-transfer efficiency for the terbium ion. All the terbium complexes emitted green fluorescence characteristic of terbium ions, possessed strong fluorescence intensity, and showed relatively high fluorescence quantum yields. Cyclic voltammograms of the terbium complexes were studied and the highest occupied molecular orbital (HOMO) and lowest occupied molecular orbital (LUMO) energy levels of these complexes were estimated.
- Xiao, Haihua,Jiang, Xi,Li, Dong,Wu, Limin,Zhang, Wu,Guo, Dongcai
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p. 677 - 685
(2015/12/04)
-
- Design, synthesis, molecular docking and 3D-QSAR studies of potent inhibitors of enoyl-acyl carrier protein reductase as potential antimycobacterial agents
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In order to develop a lead antimycobacterium tuberculosis compound, a series of 52, novel pyrrole hydrazine derivatives have been synthesized and screened which target the essential enoyl-ACP reductase. The binding mode of the compounds at the active site of enoyl-ACP reductase was explored using surflex-docking method. The binding model suggests one or two hydrogen bonding interactions between pyrrole hydrazones and InhA enzyme. Highly active compound 5r (MIC 0.2 μg/mL) showed hydrogen bonding interactions with Tyr158 and NAD+ in the same manner as those of ligands PT70 and triclosan. The CoMFA and CoMSIA models generated with database alignment were the best in terms of overall statistics. The predictive ability of the CoMFA and CoMSIA models was determined using a test set of 13 compounds, which gave predictive correlation coefficients (rpred2) of 0.896 and 0.930, respectively.
- More, Uttam A.,Joshi, Shrinivas D.,Aminabhavi, Tejraj M.,Gadad, Andanappa K.,Nadagouda, Mallikarjuna N.,Kulkarni, Venkatrao H.
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p. 199 - 218
(2014/01/06)
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- Anthelmintic evaluation of some novel synthesized 1,2,4-triazole moiety clubbed with benzimidazole ring
-
A series of N-[3-{(1H-benzo[d]imidazol-2-ylthio) methyl}-5-mercapto-4H-1,2, 4-triazol-4-yl]-2-substituted phenoxy acetamide 6(a-g) were synthesized by the mixture of the compound of potassium 2-(2-(1H-benzo[d]imidazol-2-ylthio) acetyl) hydrazinecarbodithioate (4) and arytoxy acid hydrazide (5) in presence of hydrochloric acid. The predicted structures of the synthesized compounds were confirmed by different spectral analysis studies. The title compounds 6(a-g) were screened for anthelmintic activity against Pheretima posthumous. The entire compounds were exhibited good anthelmintic activity when compared with standard drugs such as Albendazole and Piperazine.
- Kumar, P. Sudhir,Sahoo
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p. 211 - 217
(2014/06/23)
-
- An electron-deficient metallocavitand with an unusual selectivity towards substituted benzene derivatives during co-crystallizations
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A double-wall-hourglass-shaped metallocavitand bearing an electron-deficient cavity was self-assembled, which exhibited an unusual selectivity to substituted benzene derivatives of different electron density during co-crystallizations.
- Huang, Chang-Cang,Liu, Jian-Jun,Chen, Yong,Lin, Mei-Jin
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supporting information
p. 11512 - 11514
(2013/12/04)
-
- Synthesis and evaluation of antibacterial and antifungal activities of some novel 2,5-disubstituted-1,3,4-oxadiazoles
-
4-Chlorophenoxy acetic acid 2 was prepared by the condensation of phenol with monochloroacetic acid. Compound 2 was refluxed with ethanol in the presence of HCI gas yielding ethyl (4-chlorophenoxy) acetate 3. Compound 3 was refluxed with hydrazine hydrate in ethanol which produced 2-(4-chlorophenoxy) acetohydrazide 4. Compound 5a was synthesized by refluxing 2-(4-chlorophenoxy) acetohydrazide 4 with carbon disulfide and KOH in the presence of ethanol. Compound 5a on condensation with pbenzoquinone yielded 2-({4-[(4-chlorophenoxy) methyl]-1,3-4-oxadiazole-2-yl} sulfanyl) benzene-1,4-diol 5b. Oxadiazoles 6a-d were prepared by reacting substituted phenoxy acetic acids with 2-(4-chlorophenoxy) acetohydrazide 4 in the presence of POCI3. Further Schiff bases were synthesized by the reaction of substituted aldehydes with 2-(4-chlorophenoxy) acetohydrazide 4 in presence of ethanol. These Schiff bases on reaction with acetic anhyd gave the corresponding 3-acetyl-2,3-dihydro 1,3,4-oxadiazoles 7ad. Synthesized compounds were characterized on the basis of spectral and analytical data. All the compounds were screened for antimicrobial activity.
- Joshi,Unale,Parkale,Nadagouda,Gadaginamath,Ashalata
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p. 319 - 322
(2013/09/24)
-
- Synthesis and antimicrobial activity of phthalazines and pyridazines
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A new series of 2,3-dihydro phthalazine-1,4-diones, Va-b and 2,3,4,5-tetrahydro pyridazine-3,6-diones Vla-b were synthesized using p-chloro phenol and p-bromo phenol, as starting materials. The final compounds were prepared by reacting corresponding hydrazides with phthalic anhydride and succinic anhydride to get Va-b, Vla-b by fusion reaction. Structures of the synthesized compounds were confirmed on the basis of physical and spectral data (IR, 1H NMR and Mass). All the synthesized compounds were screened for their antimicrobial activity. Minimum inhibitory cone for the synthesized compounds were determined by using broth micro dil method. Among the synthesized compounds, compound Vb, having bromine at para position of the aromatic ring was found to be active at the lowest cone of 0.005 μM/ml against Gram positive bacteria Bacillus subtilis as compared to standard Ciprofloxacin, Norfloxacin and compound Vb was found active at the concentration of 0.005 μM/ml against fungi Candida albicans as compared to standard Fluconazole and Griseofulvin.
- Purohit, Shriram S.,Patil, Pavan A.
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p. 269 - 272
(2013/09/24)
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- Synthesis and xanthine oxidase inhibitory activity of 7-methyl-2- (phenoxymethyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one derivatives
-
An elevated level of blood uric acid (hyperuricemia) is the underlying cause of gout. Xanthine oxidase is the key enzyme that catalyzes the oxidation of hypoxanthine to xanthine and then to uric acid. Allopurinol, a widely used xanthine oxidase inhibitor is the most commonly used drug to treat gout. However, a small but significant portion of the population suffers from adverse effects of allopurinol that includes gastrointestinal upset, skin rashes and hypersensitivity reactions. Moreover, an elevated level of uric acid is considered as an independent risk factor for cardiovascular diseases. Therefore use of allopurinol-like drugs with minimum side effects is the ideal drug of choice against gout. In this study, we report the synthesis of a series of pyrimidin-5-one analogues as effective and a new class of xanthine oxidase inhibitors. All the synthesized pyrimidin-5-one analogues are characterized by spectroscopic techniques and elemental analysis. Four (6a, 6b, 6d and 6f) out of 20 synthesized molecules in this class showed good inhibition against three different sources of xanthine oxidase, which were more potent than allopurinol based on their respective IC50 values. Molecular modeling and docking studies revealed that the molecule 6a has very good interactions with the Molybdenum-Oxygen-Sulfur (MOS) complex a key component in xanthine oxidase. These results highlight the identification of a new class of xanthine oxidase inhibitors that have potential to be more efficacious, than allopurinol, to treat gout and possibly against cardiovascular diseases.
- Sathisha,Khanum, Shaukath A.,Chandra, J.N. Narendra Sharath,Ayisha,Balaji,Marathe, Gopal K.,Gopal, Shubha,Rangappa
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experimental part
p. 211 - 220
(2011/03/17)
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- Synthesis and antimicrobial studies of 4-oxo-thiazolidine derivatives
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Ethyl (4-chlorophenoxy)acetate (1) upon condensation with hydrazine hydrate gave 2-(4-chlorophenoxy)-acetohydrazide (2) which by condensation with aromatic aldehydes gave 2-(4-chlorophenoxy)-N-(substitutedbenzylidene) acetohydrazide (3a-k). Derivatives (3
- Patel, Hitesh D.,Mistry,Desai
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experimental part
p. 287 - 292
(2010/04/05)
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- Convenient synthesis of 4H-1,2,4-triazole-3-thiols using di-2-pyridylthionocarbonate
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We report here the convenient synthesis of 4H-1,2,4-triazole-3-thiols using di-2-pyridyl-thionocarbonate as the thiocarbonyl transfer reagent. This method is suitable for microplate parallel synthesis and produces samples in screening-ready condition. It
- Deprez-Poulain, Rebecca F.,Charton, Julie,Leroux, Virginie,Deprez, Benoit P.
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p. 8157 - 8162
(2008/03/13)
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- Synthesis and antimicrobial studies on novel chloro-fluorine containing hydroxy pyrazolines
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A series of chloro-fluorine containing chalcones (3) were prepared by Claisen-Schmidt condensation. Chalcone dibromides (4) were obtained by the bromination of chalcones at room temperature. Treatment of chalcone dibromides (4) with aryloxy acid hydrazide
- Karthikeyan, Mari Sithambaram,Holla, Bantwal Shivarama,Kumari, Nalilu Suchetha
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- A rapid and high-yield synthesis of aryloxyacetyl hydrazides under microwave irradiation and with phase transfer catalysis
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A series of aryloxyacetyl hydrazides 4a-l were synthesised under microwave irradiation and phase transfer catalysis conditions. By the optimisation of the reaction conditions, a rapid, high-yield and efficient method for the preparation of aryloxyacety hydrazide was given.
- Wei, Tai-Bao,Liu, Hong,Li, Man-Lin,Zhang, You-Ming
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p. 432 - 433
(2007/10/03)
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- Synthesis of Aryloxyacetic Acids, Esters, and Hydrazides Assisted by Microwave Irradiation
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Under microwave irradiation on clay a series of transformations of a number of phenols into their aryloxyacetic acids 3 and then their methyl esters 4 and hydrazides 5 has been achieved efficiently in good yields.
- Hamid, Hamida M. Abdel,Ramadan, El Sayed,Hagar, Mohamed,El Ashry, El Sayed H.
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p. 377 - 382
(2007/10/03)
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- Synthesis and antibacterial activity of N-bridged heterocycles derived from aryloxymethyltriazoles
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Reactions of 3-aryloxymethyl-4-amino-5-mercapto-1,2,4-triazoles 1 with aromatic carboxylic acids, furoic acid, oxalic acid, monochloroacetic acid and phenacyl bromide furnish various N-bridged heterocycles viz., triazolothiadiazoles, bistriazolothiadiazoles, triazolothiadiazinones and triazolothiadiazines. The structures of these N-bridged heterocycles are characterized on the basis of elemental analyses, IR, NMR and mass spectral data. Some of these compounds are also subjected to antibacterial screening studies.
- Shivarama Holla,Shridhara,Shivananda
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p. 1257 - 1262
(2007/10/03)
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- Synthesis and quantitative structure - Activity relationships of new 2,5-disubstituted-1,3,4-oxadiazoles
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Fourteen new 2,5-disubstituted-1,3,4-oxadiazoles, namely (i) six 2-[2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropyl]-5-substituted-1,3,4-oxadia zoles and (ii) eight 2-substituted-phenoxymethyl-5-substituted-aryl-1,3,4-oxadiazoles, were synthesized and evaluated for their insect growth regulatory activity against second-instar larvae of armyworm (Pseudaletia separata Walker). Two of these compounds (7 and 8) showed good insecticidal activities, with LC50 values of 14.33 and 15.85 μg/mL, respectively. Steric parameters (e.g., the molecular length d and the ratio of the nonpolar surface area and polar surface area V1/V2) and semiempirical quantum parameters (e.g., the molecular total energy Et and the lowest unoccupied molecular orbital energy ELUMO and so on) of these compounds, as well as those of six other 2,5-disubstituted-1,3,4-oxadiazoles reported, were acquired by the molecular modeling method and the PM3-SCF-MO method, respectively. With the help of the synthons' activity contribution method based on the Free-Wilson approach in its Fujita-Ban variant, quantitative structure-activity relationships were studied by regressing half-lethal concentrations against the above parameters.
- Shi, Wei,Qian, Xuhong,Zhang, Rong,Song, Gonghua
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p. 124 - 130
(2007/10/03)
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- Synthesis and in-vitro antimicrobial activity of new 1,2,4-triazoles
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We have described the synthesis of new 1,2,4-triazoles and have evaluated their antimicrobial profile. Antitubercular activity was determined in triplicate using the Lowenstein-Jensen medium. A loopful of Mycobacterium tuberculosis suspension was inoculated on the surface of each Lowenstein-Jensen media containing the test compounds (100, 10 or 1 μg mL-1). To evaluate in-vitro antibacterial activity, compounds (50, 5 or 0.5 μg) were evaluated against B. subtilis, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Staphylococcus typhi by the disc diffusion method. To evaluate antifungal activity Sabourauds Dextrose agar medium was used. Some of the compounds (5, 0.5 or 0.05 μg mL-1) were screened for activity against Aspergillus niger 88 and Aspergillus niger 90 and others were screened for activity against T. rubrum TR1, T. rubrum R6, T. rubrum R7 and T. mentagrophyte M1, using the cup plate method. Our results show that the triazoles with a pyrazine moiety at position 3 were more active as antitubercular and antifungal agents compared with the triazoles which had a pyrazine moiety at position 4 of the molecule.
- Bhat,Bhat,Shenoy
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p. 267 - 272
(2007/10/03)
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- Synthesis and screening of certain aryloxyacetylaminoguanidines as potential antihypertensive agents
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Ethyl aryloxyacetates (2a-k) have been synthesized either by the esterification of aryloxyacetic acids (1a-j) with ethanol in the presence of concentrated sulphuric acid or by reacting potassium naphthoxides with ethyl chloroacetate in dimethylformamide. Hydrazinolysis of either 1a, b, d, f, j or 2a-k furnishes the corresponding hydrazides (3). On the other hand, the acid chlorides (4f-h) have been prepared via the reaction of 1a-f with thionyl chloride in dry benzene, which on refluxing with aminoguanidine bicarbonate in dry benzene give the target aminoguanidine hydrochlorides (5a-h). Meanwhile, the desired aminoguanidine sulphates (5a-e) have been obtained by condensing 2a-e with S-methylisothiourea sulphate in aqueous ethanol. Additionally, the new aminotriazole sulphates (6a-h) are obtained either by refluxing 2a-h with S-methylisothiourea sulphate or by fusion of 1a,b, h, j with aminoguanidine sulphate. Structures of the new compounds are based on elemental analyses and IR, 1 HNMR and mass spectral data. Pharmacological screening, indicates that some of the newly synthesized compounds exhibit significant antihypertensive activity in both normal and renal hypertensive rats. Compound 5b produces significant decrease in the heart rate of normal rats. Compounds 5f and 5g have no significant effect. Compounds 5f, g, h have inhibition effect on the isolated rabbit intestine.
- Osman,Botros,Kandeel,Khalil,Abd El-Latif
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p. 446 - 455
(2007/10/03)
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- Synthesis, Characterization, Spectral and Antifungal Properties of Some 5-Substituted-1,3,4-oxadiazole-2-thiones and Their Mannich Bases
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A series of 5-substituted aryloxymethyl-1,3,4-oxadiazole-2-thione (3a-e) and their Mannich bases 4-8 are synthesized and subjected to fungitoxic screening.The structures of these compounds are established on the basis of elemental analysis 1H-n.m.r. and mass spectral data.The mass spectral fragmentation pathways of these compounds are discussed.
- Holla, B. Shivarama,Kalluraya, Balakrishna,Nath, S. C.
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p. 549 - 557
(2007/10/02)
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