- Synthesis and screening of some novel substituted indoles contained 1,3,4-oxadiazole and 1,2,4-triazole moiety
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A series of novel 3-[5-(1H-indol-3-yl-methyl)-2-oxo-[1,3,4]oxadiazol-3-yl] propionitrile (5), 3-[4-amino-3-(1H-indol-3-yl-methyl)-5-oxo-4,5-dihydro-[1,2,4] triazol-1-yl]propionitrile (6), 3-[5-(1H-indol-3-yl-methyl)-2-thioxo-[1,3,4] oxadiazol-3-yl]propionitrile (7) and 3-[4-amino-3-(1H-indol-3-yl-methyl)-5- thioxo-4,5-dihydro-[1,2,4]triazol-1-yl]propionitrile (8) were synthesized in good yields from the intermediate (1H-indol-3-yl)-acetic acid N′-(2-cyanoethyl)hydrazide (4). The chemical structures of the newly synthesized compounds were elucidated by their IR, 1H NMR and MS. Further, all the compounds were screened for their antimicrobial activity against Gram-positive, Gram-negative bacteria and also tested their ability toward anti-inflammatory activity.
- Gadegoni, Hemalatha,Manda, Sarangapani
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- A new CDK2 inhibitor with 3-hydrazonoindolin-2-one scaffold endowed with anti-breast cancer activity: Design, synthesis, biological evaluation, and in silico insights
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Background: Cyclin-dependent kinases (CDKs) regulate mammalian cell cycle progression and RNA transcription. Based on the structural analysis of previously reported CDK2 inhibitors, a new compound with 3-hydrazonoindolin-2-one scaffold (HI 5) was well designed, synthesized, and biologically evaluated as a promising anti-breast cancer hit compound. Methods: The potential anti-cancerous effect of HI 5 was evaluated using cytotoxicity assay, flow cytometric analysis of apoptosis and cell cycle distribution, ELISA immunoassay, in vitro CDK2/cyclin A2 activity, and molecular operating environment (MOE) virtual docking studies. Results: The results revealed that HI 5 exhibits pronounced CDK2 inhibitory activity and cytotoxicity in human breast cancer MCF-7 cell line. The cytotoxicity of HI 5 was found to be intrinsically mediated apoptosis, which in turn, is associated with low Bcl-2 expression and high activation of caspase 3 and p53. Besides, HI 5 blocked the proliferation of the MCF-7 cell line and arrested the cell cycle at the G2/M phase. The docking studies did not confirm which one of geometric isomers (syn and anti) is responsible for binding affinity and intrinsic activity of HI 5. However, the molecular dynamic studies have confirmed that the syn-isomer has more favorable binding interaction and thus is responsible for CDK2 inhibitory activity. Discussion: These findings displayed a substantial basis of synthesizing further derivatives based on the 3-hydrazonoindolin-2-one scaffold for favorable targeting of breast cancer.
- Al-Sanea, Mohammad M.,Obaidullah, Ahmad J.,Shaker, Mohamed E.,Chilingaryan, Garri,Alanazi, Mohammed M.,Alsaif, Nawaf A.,Alkahtani, Hamad M.,Alsubaie, Sultan A.,Abdelgawad, Mohamed A.
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- Diversity-oriented synthesis and antifungal activities of novel pimprinine derivative bearing a 1,3,4-oxadiazole-5-thioether moiety
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Abstract: Based on the strategy of diversity-oriented synthesis and the structures of natural product pimprinine and streptochlorin, two series of novel pimprinine derivatives containing 1,3,4-oxadiazole-5-thioether moieties were efficiently synthesized under the optimized reaction conditions. Biological assays conducted at Syngenta showed the designed derivatives displayed an altered pattern of biological activity, of which 5h was identified as the most promising compound with strong activity against Pythium dissimile and also a broad antifungal spectrum in primary screening. Further structural optimization of pimprinine and streptochlorin derivatives is well under way, aiming to discover synthetic analogues with improved antifungal activity. Graphic abstract: Two series of novel pimprinine derivatives containing 1,3,4-oxadiazole-5-thioether moieties wereefficiently synthesized through diversity-oriented synthesis strategy under the optimizedconditions. Biological assays showed the designed derivatives exhibited potential activity.[Figure not available: see fulltext.].
- Song, Zi-Long,Zhu, Yun,Liu, Jing-Rui,Guo, Shu-Ke,Gu, Yu-Cheng,Han, Xinya,Dong, Hong-Qiang,Sun, Qi,Zhang, Wei-Hua,Zhang, Ming-Zhi
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p. 205 - 221
(2020/02/18)
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- Synthesis, Pharmacological Evaluation and Molecular Docking Studies of N-[2-(1H-indol-3-yl)Acetyl]Arylsulfonohydrazides
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Synthesis of heterocyclic compounds encompassing multiple functionalities and their biological screening is the most adapted strategy in the world for pharmacological evaluation of future drug candidates. The undertaken research was initiated by esterification 2-(1H-indol-3-yl)acetic acid (1) with catalytic amount of sulfuric acid in ethanol to ethyl 2-(1H-indol-3-yl)acetate (2), which was then reacted with hydrazine hydrate in methanol to achieve 2-(1H-indol-3-yl)acetohydrazide (3). The corresponding hydrazide 3 was reacted with a variety of arylsulfonyl chlorides (4a-j) in sodium carbonate solution (pH 9-10) to afford N-[2-(1H-indol-3-yl)acetyl]arylsulfonohydrazides (5a-j). The structural characterization of synthesized compounds was done by 1H-NMR, 13C-NMR, IR and EI-MS spectral data. Moreover, these derivatives were evaluated for anti-bacterial potentials along with their % age hemolytic and enzyme inhibitory activities. It was found that compounds 5a, 5b, 5d and 5h revealed good anti-bacterial against all the bacterial strains used in this study, while 5d, 5g and 5h exhibited good enzyme inhibition potentials against BChE which were close to the reference standard eserine. These compounds also revealed low values of % hemolytic activity. Results of computational docking were also found in agreement with the enzyme inhibition data.
- Abbasi, M. A.,Ahmad, I.,Ashraf, M.,Aziz-ur-Rehman,Fatima, Hina,Khan, F. A.,Lodhi, M. A.,Qurat-ul-Ain,Rubab, K.,Shah, S. A. A.,Shahid, M.,Siddiqui, S. Z.
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p. 665 - 678
(2021/10/30)
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- Investigation of indole functionalized pyrazoles and oxadiazoles as anti-inflammatory agents: Synthesis, in-vivo, in-vitro and in-silico analysis
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There are several potential side and adverse effects are found to be associated with the anti-inflammatory drugs in clinical practice. The long-term use of these clinical agents highly unsafe. It encouraged the development of novel heterocyclic compounds with potential anti-inflammatory activity and low to no toxicity. In present investigation, a total of 12 indole functionalized pyrazole and oxadiazole derivatives were designed, synthesized and evaluated for the in-vivo anti-inflammatory and analgesic potential. These compounds displayed comparable anti-inflammatory and analgesic potential to the reference drugs. Finally, molecular docking analysis was performed considering different anti-inflammatory targets to determine the mechanistic target of the designed molecules. Detailed analysis suggested that the molecules inhibit COX-2, preferably over other anti-inflammatory targets. The results suggested that two compounds (15c and 15f) were found promising candidates for the development of novel anti-inflammatory agents.
- Kalra, Sourav,Kumar, Bhupinder,Kumar, Devendra,Kumar, Ravi Ranjan,Pathania, Shelly,Singh, Pankaj Kumar
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- Synthesis of 5-[(1H-indol-3-yl)methyl]-1,3,4-oxadiazole-2(3H)-thiones and their protective activity against oxidative stress
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A small library of 2-[(1H-indol-3-yl)methyl]-5-(alkylthio)-1,3,4-oxadiazoles was prepared, starting from indole-3-acetic acid methyl ester and its 5-methyl-substituted derivative. The synthetic route involved the formation of intermediate hydrazides, their condensation with carbon disulfide, and intramolecular cyclization to corresponding 5-[(1H-indol-3-yl)methyl]-1,3,4-oxadiazole-2(3H)-thiones. The latter were then S-alkylated, and in case of ester derivatives, they were further hydrolyzed into corresponding carboxylic acids. All 5-[(1H-indol-3-yl)methyl]-1,3,4-oxadiazole-2(3H)-thiones and their S-alkylated derivatives were then screened for their protective effects in vitro and in vivo. Methyl substitution on the indole ring and propyl, butyl, or benzyl substitution on sulfhydryl group-possessing compounds were revealed to protect Friedreich's ataxia fibroblasts against the effects of glutathione depletion induced by the γ-glutamylcysteine synthetase inhibitor, buthionine sulfoximine. Two of the active compounds also reproducibly increased the survival of Caenorhabditis elegans exposed to juglone-induced oxidative stress.
- I?kauskien?, Monika,Kadlecová, Alena,Voller, Ji?í,Janovská, Lucie,Malinauskien?, Vida,?ukauskait?, Asta,?a?kus, Algirdas
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- Synthesis of new urease enzyme inhibitors as antiulcer drug and computational study
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In search of potent urease inhibitor indole analogues (1–22) were synthesized and evaluated for their urease inhibitory potential. All analogues (1–22) showed a variable degree of inhibitory interaction potential having IC50 value ranging between 0.60 ± 0.05 to 30.90 ± 0.90 μM when compared with standard thiourea having IC50 value 21.86 ± 0.90 μM. Among the synthesized analogues, the compounds 1, 2, 3, 5, 6, 8, 12, 14, 18, 20 and 22 having IC50 value 3.10 ± 0.10, 1.20 ± 0.10, 4.60 ± 0.10, 0.60 ± 0.05, 5.30 ± 0.20, 2.50 ± 0.10, 7.50 ± 0.20, 3.90 ± 0.10, 3.90 ± 0.10, 2.30 ± 0.05 and 0.90 ± 0.05 μM respectively were found many fold better than the standard thiourea. All other analogues showed better urease interaction inhibition. Structure activity relationship (SAR) has been established for all analogues containing different substituents on the phenyl ring. To understand the binding interaction of most active analogues with enzyme active site docking study were performed. Communicated by Ramaswamy H. Sarma.
- Taha, Muhammad,Ismail, Sukinah,Imran, Syahrul,Almandil, Noor Barak,Alomari, Munther,Rahim, Fazal,Uddin, Nizam,Hayat, Shawkat,Zaman, Khalid,Ibrahim, Mohamad,Alghanem, Bandar,Islam, Imadul,Farooq, Rai Khalid,Boudjelal, Mohamed,Khan, Khalid Mohammed
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- Marine-inspired bis-indoles possessing antiproliferative activity against breast cancer; design, synthesis, and biological evaluation
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Diverse indoles and bis-indoles extracted from marine sources have been identified as promising anticancer leads. Herein, we designed and synthesized novel bis-indole series 7a-f and 9a-h as Topsentin and Nortopsentin analogs. Our design is based on replacing the heterocyclic spacer in the natural leads by a more flexible hydrazide linker while sparing the two peripheral indole rings. All the synthesized bis-indoles were examined for their antiproliferative action against human breast cancer (MCF-7 and MDA-MB-231) cell lines. The most potent congeners 7e and 9a against MCF-7 cells (IC50 = 0.44 ± 0.01 and 1.28 ± 0.04 μM, respectively) induced apoptosis in MCF-7 cells (23.7-, and 16.8-fold increase in the total apoptosis percentage) as evident by the externalization of plasma membrane phosphatidylserine detected by Annexin V-FITC/PI assay. This evidence was supported by the Bax/Bcl-2 ratio augmentation (18.65- and 11.1-fold compared to control) with a concomitant increase in the level of caspase-3 (11.7- and 9.5-fold) and p53 (15.4- and 11.75-fold). Both compounds arrested the cell cycle mainly in the G2/M phase. Furthermore, 7e and 9a displayed good selectivity toward tumor cells (S.I. = 38.7 and 18.3), upon testing of their cytotoxicity toward non-tumorigenic breast MCF-10A cells. Finally, compounds 7a, 7b, 7d, 7e, and 9a were examined for their plausible CDK2 inhibitory action. The obtained results (% inhibition range: 16%-58%) unveiled incompetence of the target bis-indoles to inhibit CDK2 significantly. Collectively, these results suggested that herein reported bis-indoles are good lead compounds for further optimization and development as potential efficient anti-breast cancer drugs.
- Eldehna, Wagdy M.,Hassan, Ghada S.,Al-Rashood, Sara T.,Alkahtani, Hamad M.,Almehizia, Abdulrahman A.,Al-Ansary, Ghada H.
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- A double-indole hydrazone compound and use thereof
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The invention provides a bisindole acylhydrazone compound shown as the formula I or salt, hydrate or crystals, accepted in the pharmacy, of the bisindole acylhydrazone compound. According to the bisindole acylhydrazone compound, R does not exist or is selected from alkylene of C1-5. The bisindole acylhydrazone compound has a certain antibacterial activity, and can serve as potential antibiotics or a daily chemical product. What is beyond the expectation is that compounds 4e-4h and compounds 4a-4c are quite similar in structure, the antibacterial activity of the compounds 4e-4h and the antibacterial activity of the compounds 4a-4c are obviously better than that of other compounds, particularly, the activity of the compound 4h is best and is remarkably better than that of compounds 4e-4g. The formula I is shown in the specification.
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Paragraph 0036; 0041
(2017/10/06)
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- Indole hydrazone compounds
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The invention provides a compound of the formula I as shown in the description. In the formula, R is connected with the carbon atom at the 2nd or 3rd site of indolyl and is selected from none or C1-3 alkylene. Molecular tweezers of bisindole acylhydrazone have a good recognition cooperation function on inspected malic acid, tartaric acid, ascorbic acid and tryptophan, and have no recognition cooperation function on other inspected organic acids such as lactic acid, oxalic acid, tyrosine, histidine and serine. Therefore, due to the selective recognition property of a molecular tweezers receptor has the potential to be applied to fields such as analysis and separation of relevant organic acids in biological medicines, and transportation of organic acid medicines.
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Paragraph 0039; 0040; 0043; 0044; 0047
(2017/11/17)
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- N'-(2-(1H-indole-3-yl)acetyl)arylhydrazide compound and preparation method and application thereof
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The invention provides a N'-(2-(1H-indole-3-yl)acetyl)arylhydrazide compound and a preparation method and application thereof.The N'-(2-(1H-indole-3-yl)acetyl)arylhydrazide compound has a structure shown as a formula I (please see the formula in the description) and has the obvious inhibiting effect on an HCV virus, the anti-HCV virus treatment index is higher than that of existing clinical drugs including alpha-1b(IFNalpha-1b) interferon and ribavirin, and the N'-(2-(1H-indole-3-yl)acetyl)arylhydrazide compound can serve as an anti-HCV drug candidate; in addition, the preparation method is simple, high in yield and suitable for industrial production.
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- Tryptophan and thiosemicarbazide derivatives: Design, synthesis, and biological evaluation as potential β-D-galactosidase and β-D-glucosidase inhibitors
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Glycosidases, including β-D-galactosidase and β-D-glucosidase, are involved in a range of metabolic disorders, such as cancer, viral or bacterial infections, and diabetes. Previously, we scanned the pharmacophoric space of these enzymes and had a self-consistent and predictive quantitative structure-activity relationship that was used to identify several β-D-galactosidase and β-D-glucosidase inhibitors via in silico search of structural databases. Guided by the preceding modeling efforts, synthesis of a series of tryptophan and thiosemicarbazide derivatives as β-D-galactosidase and β-D-glucosidase inhibitors that match the generated pharmacophores followed by in vitro bioassay was carried out. Synthesized compounds 3c (37 % inhibition at 100 μM) and 4d (49 % inhibition at 100 μM) exhibited the best inhibitory bioactivities against β-D-galactosidase and β-D-glucosidase, respectively. They can serve as a promising lead compounds for the development of potential glycosidase inhibitors.
- Abu Khalaf, Reema,Abdula, Ahmed Mutanabbi,Mubarak, Mohammad S.,Taha, Mutasem O.
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p. 2529 - 2550
(2015/06/22)
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- Synthesis of 3-hydroxyindanones via potassium salt of amino acid catalyzed regioselective intramolecular aldolization of ortho-diacylbenzenes
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First organocatalytic intramolecular aldolization of ortho-diacylbenzenes to construct highly functionalized 3-hydroxyindanones is described. In this transformation a high trans-selectivity is achieved by the use of metal salt of amino acid. This method allows an easy access to the strained spirocyclic 3-hydroxyindanones related to a number of natural product frameworks. Synthesis of a new class of indole skeleton substituted by 3-hydroxyindanones added an extra essence to this new protocol.
- Chanda, Tanmoy,Chowdhury, Sushobhan,Anand, Namrata,Koley, Suvajit,Gupta, Ashutosh,Singh, Maya Shankar
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supporting information
p. 981 - 985
(2015/03/04)
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- Microwave-assisted synthesis and molecular recognition properties of novel indole acylhydrazone receptors
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Indole acylhydrazones were synthesised in high yields under microwave irradiation By using indole carboxylic acid and 1,4-benzenedialdehyde as starting materials. Their structures were characterised by 1H NMR, IR, MS spectra and elemental analysis. Selective recognition properties of these receptors have been investigated by UV-Vis spectra titration indicating that these receptors can form 1:1 supramolecular complexes with malic acid, tartaric acid, ascorbic acid and tryptophan.
- Ye, Ying,Suo, Yourui,Yang, Fang,Yang, Yongjing,Han, Lijuan
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p. 296 - 299
(2015/06/02)
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- Synthesis, in vitro lipoxygenase inhibition, docking study and thermal stability analyses of novel indole derivatives: Non-isothermal kinetic study of potent LOX inhibitor N'-(diphenylmethylene)-2-(1H-indole-3-yl) acetohydrazide
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A series of indole derivatives has been synthesized and biologically evaluated to identify potent new lipoxygenase (LOX) inhibitors. All selected indole derivatives were screened for their LOX inhibition studies. Most of compounds showed good in vitro LOX inhibition properties exhibiting IC 50 values in the range of 53.61 ± 0.14 to 198.61 ± 0.11 μM (mean ± SEM), as compared to the standard inhibitor baicalein with IC50 value 22.4 ± 1.3 μM. Structure activity relationship has been discussed and docking stimulation of most active compound 4f has also performed. Thermal stability and melting point of indole derivatives have been performed by thermal gravimetric analysis and differential scanning calorimetry analysis under nitrogen atmosphere at heating rate of 20 C min-1. Compound 4f bearing bis-phenyl moiety has been found to be the most potent (IC50 53.61 ± 0.14 μM) and thermally most stable among the tested compounds. Imine (C=N) was found to be the key moiety for increasing the thermal stabilities of indole derivatives. FT-IR, NMR and elemental analysis techniques were performed for structural characterization.
- Yar, Muhammad,Sidra, Lala Rukh,Pontiki, Eleni,Mushtaq, Nafeesa,Ashraf, Muhammad,Nasar, Rumana,Khan, Islam Ullah,Mahmood, Nasir,Naqvi, Syed Ali Raza,Khan, Zulfiqar Ali,Shahzad, Sohail Anjum
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p. 369 - 378
(2014/04/03)
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- Design and synthesis of new dual binding site cholinesterase inhibitors: In vitro inhibition studies with in silico docking
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Cholinesterases (ChEs) play a vital role in the regulation of cholinergic transmission. The inhibition of ChEs is considered to be involved in increasing acetylcholine level in the brain and thus has been implicated in the treatment of Alzheimer's disease. We have designed and synthesized a series of novel indole derivatives and screened them for inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Most of the tested compounds exhibited inhibitory activity against AChE and BChE. Among them 4f and 6e showed the highest AChE inhibitory activity with IC50 91.21±0.06 and 68.52±0.04 μM, respectively. However compound 5a exhibited the highest inhibitory activity against BChE (IC50 55.21±0.12 μM).
- Yar, Muhammad,Bajda, Marek,Mehmood, Rana Atif,Sidra, Lala Rukh,Ullah, Nisar,Shahzadi, Lubna,Ashraf, Muhammad,Ismail, Tayaba,Shahzad, Sohail Anjum,Khan, Zulfiqar Ali,Naqvi, Syed Ali Raza,Mahmood, Nasir
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p. 331 - 338
(2014/03/21)
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- DI-AND TRI-HETEROARYL DERIVATIVES AS INHIBITORS OF PROTEIN AGGREGATION
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The present invention relates to certain di- and tri-heteroaryl derivatives, pharmaceutical compositions containing them, and methods of using them, including methods for preventing, reversing, slowing, or inhibiting protein aggregation, and methods of treating diseases that are associated with protein aggregation, including neurodegenerative diseases such as Parkinson's disease, Alzheimer's disease, Lewy body disease, and multiple system atrophy.
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Paragraph 0115
(2014/02/15)
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- Synthesis and antifungal activity of 3-(1,3,4-oxadiazol-5-yl)-indoles and 3-(1,3,4-oxadiazol-5-yl)methyl-indoles
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On the basis of the principle of combination of active structural moieties, a modified and efficient synthetic method for three series of novel indole-based 1,3,4-oxadiazoles is described. Bioassays conducted at Syngenta showed that several of the synthesized compounds exhibit higher antifungal activity than pimprinine, the natural product which inspired this synthesis. Two main structural alterations were found to broaden the spectrum of biological activity in most cases. Compounds 3g, 6c, 6e, 6h, 9d, 9e, 9h and 9m (Fig. 1) were identified as the most active on the biological assays, and will be studied further.
- Zhang, Ming-Zhi,Mulholland, Nick,Beattie, David,Irwin, Dianne,Gu, Yu-Cheng,Chen, Qiong,Yang, Guang-Fu,Clough, John
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- A series of 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles as potent cytotoxic agents
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A series of 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles 6a-v were prepared and studied for their anticancer activity against selected human cancer cell lines. The reaction of indolylhydrazides 3a-h with a variety of aryl isothiocyanates 4 afforded the key intermediate thiosemicarbazides 5a-v, which upon treatment with acetyl chloride produced the 2-arylamino-5-(indolyl)-1,3,4- thiadiazoles 6a-v in good yields. Most of the synthesized compounds showed selective cytotoxicity towards human breast cancer cell line (MDA-MB-231). Of the synthesized 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles, compound 6f is the most potent towards tested cancer cell lines (IC50 = 0.15-1.18 μM).
- Kumar, Dalip,Kumar, N. Maruthi,Noel, Brett,Shah, Kavita
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p. 432 - 438
(2012/11/07)
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- Synthesis and pharmacological in vitro and in vivo evaluations of novel triazole derivatives as ligands of the ghrelin receptor. 1
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A new series of growth hormone secretagogue (GHS) analogues based on the 1,2,4-triazole structure were synthesized and evaluated for their in vitro binding and their ability to stimulate intracellular calcium release to the cloned hGHS-1a ghrelin receptor expressed in LLC PK-1 cells. We have synthesized potent ligands of this receptor, some of them behaving as agonists, partial agonists, or antagonists. Some compounds among the most potent, i.e., agonist 29c (JMV2873), partial agonists including 21b (JMV2810), antagonists 19b (JMV2866) and 19c (JMV2844), were evaluated for their in vivo activity on food intake, after sc injection in rodents. Some compounds were found to stimulate food intake like hexarelin; some others were identified as potent hexarelin antagonists in this assay. Among the tested compounds, 21b was identified as an in vitro ghrelin receptor partial agonist, as well as a potent in vivo antagonist of hexarelin-stimulated food intake in rodents. Compound 21b was without effect on GH release from rat. However, in this series of compounds, it was not possible to find a clear correlation between in vitro and in vivo results.
- Demange, Luc,Boeglin, Damien,Moulin, Aline,Mousseaux, Delphine,Ryan, Joanne,Bergé, Gilbert,Gagne, Didier,Heitz, Annie,Perrissoud, Daniel,Locatelli, Vittorio,Torsello, Antonio,Galleyrand, Jean-Claude,Fehrentz, Jean-Alain,Martinez, Jean
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p. 1939 - 1957
(2008/02/02)
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- Synthesis and biological screening of 2-substituted 5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitriles and of their intermediates
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To evaluate the effect of substituents on biological activities of electron-rich N-containing heterocycles, the variably 2-substituted 5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitriles 26-33 were synthesized and evaluated for antibacterial, antifungal, and enzyme-inhibition activities. The target compounds were obtained from alkyl 4- or 3-hydroxy benzoates 1 and 2, respectively, and from methyl indoleacetate 3. The phenolic OH group of benzoates 1 and 2 were substituted with p-toluenesulfonyl (→ 4 and 5), benzoyl (→ 6 and 7), and benzyl groups (→ 8 and 9) and then converted to 5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitriles. To establish structure-activity relationships (SAR), a pharmacological screening of the intervening intermediates was also conducted, which revealed that the intermediate hydrazide 11 possesses significant antimicrobial and MAO-A inhibiting properties and intermediates 12, 24, 28, and 29 appreciable antifungal activities. Compound 7 inhibits α-chymotrypsin.
- Khan, Khalid Mohammed,Rahat, Shagufta,Choudhary, Muhammad Iqbal,Atta-ur-Rahman,Ghani, Usman,Perveen, Shahnaz,Khatoon, Shagufta,Dar, Ahsana,Malik, Abdul
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p. 559 - 570
(2007/10/03)
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- The Application of Levulinic Acid and 5-Nitro-2-furylmethylene Diacetate in the Total Synthesis of Some Novel Biologically Active (5-Nitro-2-furyl)azomethines
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The syntheses and in vitro antibacterial and antifungal evaluation of certain (5-nitro-2-furyl)azomethines with different heterocyclic nuclei are described.
- Vlaovic, Djordje,Cetkovic, Gordana,Juranic, Ivan,Balaz, Jelica,Lajsic, Stevan,Djokovic, Dejan
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p. 931 - 939
(2007/10/02)
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- Synthesis and properties of azoles and their derivatives. 33. Synthesis of 1,3,4-oxadiazoles that contain an indolyl group
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2,5-Disubstituted oxadiazoles with indole residues were synthesized by condensation of the hydrochlorides of the corresponding imido esters with hydrazines, as well as by cyclization of hydrazides by the action of POCl3. 2-Substituted oxadiazoles of the same series were obtained by condensation of the corresponding hydrazides with ethyl orthoformate.
- Kelarev,Shvekhgeimer
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p. 258 - 261
(2007/10/02)
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