127876-36-2Relevant academic research and scientific papers
Synthesis of benzotriazoles derivatives and their dual potential as α-amylase and α-glucosidase inhibitors in vitro: Structure-activity relationship, molecular docking, and kinetic studies
Hameed, Shehryar,Kanwal,Seraj, Faiza,Rafique, Rafaila,Chigurupati, Sridevi,Wadood, Abdul,Rehman, Ashfaq Ur,Venugopal, Vijayan,Salar, Uzma,Taha, Muhammad,Khan, Khalid Mohammed
, (2019/09/10)
Benzotriazoles (4–6) were synthesized which were further reacted with different substituted benzoic acids and phenacyl bromides to synthesize benzotriazole derivatives (7–40). The synthetic compounds (7–40) were characterized via different spectroscopic techniques including EI-MS, HREI-MS, 1H-, and 13C NMR. These molecules were examined for their anti-hyperglycemic potential hence were evaluated for α-glucosidase and α-amylase inhibitory activities. All benzotriazoles displayed moderate to good inhibitory activity in the range of IC50 values of 2.00–5.6 and 2.04–5.72 μM against α-glucosidase and α-amylase enzymes, respectively. The synthetic compounds were divided into two categories “A” and “B”, in order to understand the structure-activity relationship. Compounds 25 (IC50 = 2.41 ± 1.31 μM), (IC50 = 2.5 ± 1.21 μM), 36 (IC50 = 2.12 ± 1.35 μM), (IC50 = 2.21 ± 1.08 μM), and 37 (IC50 = 2.00 ± 1.22 μM), (IC50 = 2.04 ± 1.4 μM) with chloro substitution/s at aryl ring were found to be most active against α-glucosidase and α-amylase enzymes. Molecular docking studies on all compounds were performed which revealed that chloro substitutions are playing a pivotal role in the binding interactions. The enzyme inhibition mode was also studied and the kinetic studies revealed that the synthetic molecules have shown competitive mode of inhibition against α-amylase and non-competitive mode of inhibition against α-glucosidase enzyme.
α-N-Heteroarylation and α-Azidation of Ketones via Enolonium Species
More, Atul A.,Pathe, Gulab K.,Parida, Keshaba N.,Maksymenko, Shimon,Lipisa, Yuriy B.,Szpilman, Alex M.
, p. 2442 - 2447 (2018/02/23)
Enolonium species, resulting from the umpolung of ketone enolates by Koser's hypervalent iodine reagents activated by boron trifluoride, react with a variety of nitrogen heterocycles to form α-aminated ketones. The reactions are mild and complete in 4-5 h. Additionally, α-azidation of the enolonium species takes place using trimethylsilyl azide as a convenient source of azide nucleophile.
A METAL FREE PROCESS FOR THE PREPARATION OF ALPHA-SUBSTITUTED CARBONYL COMPOUNDS FROM ALKENES
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Page/Page column 20-21, (2017/06/19)
The present invention discloses a novel metal free process for the regioselective synthesis of α-substituted carbonyl compounds of formula I from alkene, X is selected from the following compounds (A, B).
Regioselective oxo-amination of alkenes and enol ethers with N-bromosuccinimide-dimethyl sulfoxide combination: A facile synthesis of α-amino-ketones and esters
Prasad, Pragati K.,Reddi, Rambabu N.,Sudalai, Arumugam
supporting information, p. 500 - 503 (2016/02/18)
An unprecedented conversion of alkenes and enol ethers to the corresponding α-imido carbonyl compounds with excellent regioselectivity and yields has been developed. This oxo-amination process employs readily available N-bromosuccinimide (NBS) and secondary amines as N-sources and dimethyl sulfoxide (DMSO) as the oxidant and also leads to the production of amino alcohols in a single step on reduction, thus broadening the scope of this operationally simple reaction. For the first time, the formation of reactive Me2S+-O-Br species generated by the interaction of NBS with DMSO has been proven.
Design, synthesis, and biological evaluation of 3-(1-aryl-1 h -indol-5-yl)propanoic acids as new indole-based cytosolic phospholipase a2α inhibitors
Tomoo, Toshiyuki,Nakatsuka, Takashi,Katayama, Toyoko,Hayashi, Yasuhiro,Fujieda, Yusuke,Terakawa, Maki,Nagahira, Kazuhiro
, p. 7244 - 7262 (2015/01/30)
This article describes the design, synthesis, and biological evaluation of new indole-based cytosolic phospholipase A2α (cPLA2α, a group IVA phospholipase A2) inhibitors. A screening-hit compound from our library, (E)-3-{4-[(4-chlorophenyl)thio]-3-nitrophenyl}acrylic acid (5), was used to design a class of 3-(1-aryl-1H-indol-5-yl)propanoic acids as new small molecule inhibitors. The resultant structure-activity relationships studied using the isolated enzyme and by cell-based assays revealed that the 1-(p-O-substituted)phenyl, 3-phenylethyl, and 5-propanoic acid groups on the indole core are essential for good inhibitory activity against cPLA2α. Optimization of the p-substituents on the N1 phenyl group led to the discovery of 56n (ASB14780), which was shown to be a potent inhibitor of cPLA2α via enzyme assay, cell-based assay, and guinea pig and human whole-blood assays. It displayed oral efficacy toward mice tetradecanoyl phorbol acetate-induced ear edema and guinea pig ovalbumin-induced asthma models.
A facile protocol for N-alkylation of azoles using KOtBu as base under NBS-promoted conditions
Chen, Wen-Lin,Li, Ji-Hui,Meng, Xu,Tang, Dong,Guo, Shuai-Bo,Chen, Bao-Hua
supporting information, p. 295 - 299 (2013/02/25)
A mild, transition metal-free, and environmentally benign NBS-promoted C-N bond formation of N-heterocycles is successfully demonstrated. A series of heterocyclic derivatives are readily prepared under mild conditions in moderate to good yields.
Iodine-induced regioselective direct alkylation of azoles via in situ formed alkyliodide
Chen, Wenlin,Yan, Rulong,Tang, Dong,Guo, Shuaibo,Meng, Xu,Chen, Baohua
supporting information; experimental part, p. 7956 - 7959 (2012/09/21)
We have developed an efficient, metal-free, convenient and relatively cheap method for iodine-induced direct alkylation of azoles via in situ formed alkyliodide. A series of heterocyclic derivatives are readily prepared under mild conditions in moderate t
Green and efficient protocol for N-alkylation of benzotriazole using basic ionic liquid [Bmim]OH as catalyst under solvent-free conditions
Le, Zhang-Gao,Zhong, Tao,Xie, Zong-Bo,Lue, Xue-Xia,Cao, Xia
experimental part, p. 2525 - 2530 (2010/09/14)
N-Alkylation of benzotriazole bearing an acidic hydrogen atom attached to nitrogen with alkyl halides is accomplished in basic ionic liquid [Bmim]OH (1-butyl-3-methylimidazolium hydroxide) under solvent-free conditions. The procedure is convenient and efficient and generally affords the N-alkylated product. Taylor & Francis Group, LLC.
Design and synthesis of some novel oxiconazole-like carboacyclic nucleoside analogues, as potential chemotherapeutic agents
Rad, Mohammad Navid Soltani,Khalafi-Nezhad, Ali,Behrouz, Somayeh
experimental part, p. 1760 - 1774 (2009/12/06)
The syntheses of some novel carboacyclic nucleosides, 17a-17o, containing oxiconazole-like scaffolds, are described (Schemes 1-3). In this series of carboacyclic nucleosides, pyrimidine as well as purine and other imidazole derivatives were employed as an imidazole successor in oxiconazole. These compounds could be prepared in good yields by using two different strategies (Schemes 1 and 2). Due to Scheme 1, the N-coupling of nucleobases with 2-bromoacetophenones was attained for 18a-18e, and their subsequent oximation affording 19a-19e and finally O-alkylation with diverse alkylating sources resulted in the products 17a-17g, 17n, and 17o. In Scheme 2, use of 2-bromoacetophenone oximes 20, followed by N-coupling of nucleobases, provided 19f-19j whose final O-alkylation produced 17h-17m (Scheme 2). For the rational interpretation of the dominant formation of (E)-oxime ethers rather than (Z)-oxime isomers, PM3 semiempirical quantum-mechanic calculations were discussed and the calculations indicated a lower heat of formation for (E)-isomers.
Organic reactions in ionic liquids: A simple highly regioselective or regiospecific substitutions of benzotriazole
Le, Zhang-Gao,Chen, Zhen-Chu,Hu, Yi,Zheng, Qin-Guo
, p. 1077 - 1081 (2007/10/03)
In the absence of any added base in ionic liquids [Bmim][BF4], benzotriazole replaces the halogen atom of an α-halogenated ketone or α-halogenated carboxylic ester to give the corresponding N-1-substituted benzotriazole as the only isomer, and
