- 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
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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.
- Hameed, Shehryar,Kanwal,Seraj, Faiza,Rafique, Rafaila,Chigurupati, Sridevi,Wadood, Abdul,Rehman, Ashfaq Ur,Venugopal, Vijayan,Salar, Uzma,Taha, Muhammad,Khan, Khalid Mohammed
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- Trichloroisocyanuric Acid Mediated High-Yielding Synthesis of N -Acylbenzotriazoles under Mild Reaction Conditions
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N -Acylbenzotriazoles are achieved in good yields from the corresponding carboxylic acids by using only 0.35 equivalent of trichloroisocyanuric acid and 1.2 equivalents of PPh 3. The salient features of the developed reaction path include an ec
- Singh, Mala,Singh, Anoop S.,Mishra, Nidhi,Agrahari, Anand K.,Tiwari, Vinod K.
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p. 2183 - 2190
(2019/05/10)
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- Visible-Light-Induced C(sp2)-P Bond Formation by Denitrogenative Coupling of Benzotriazoles with Phosphites
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A visible-light-induced denitrogenative phosphorylation of benzotriazoles is presented, in which diverse substituted aryl phosphonates could be obtained in good to excellent yields. This efficient protocol exhibits good tolerance with various functional g
- Jian, Yong,Chen, Ming,Huang, Binbin,Jia, Wei,Yang, Chao,Xia, Wujiong
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supporting information
p. 5370 - 5374
(2018/09/13)
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- A new methodology for the synthesis of N-acylbenzotriazoles
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A facile and economic path for an easy access of diverse N-acylbenzotriazoles from carboxylic acid has been devised using NBS/PPh3 in anhydrous dichloromethane. High yield of product was obtained at room temperature in one hour reaction time under mild reaction conditions.
- Singh, Anoop S.,Agrahari, Anand K.,Singh, Mala,Mishra, Nidhi,Tiwari, Vinod K.
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- A Biocatalytic Route to Highly Enantioenriched β-Hydroxydioxinones
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A novel biocatalytic system to access a wide variety of β-hydroxydioxinones from β-ketodioxinones employing commercial engineered ketoreductases has been developed. This practical system provides a remarkably straightforward solution to limitations in acc
- Betori, Rick C.,Miller, Eric R.,Scheidt, Karl A.
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supporting information
p. 1131 - 1137
(2017/04/11)
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- An efficient one-pot synthesis of: N, N ′-disubstituted ureas and carbamates from N -acylbenzotriazoles
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A facile and high-yielding one-pot synthesis of carbamates and N,N′-disubstituted symmetrical ureas from N-acylbenzotriazoles has been devised. It is believed that, the intermediate acyl-azide undergo Curtius rearrangement and in different solvents gives different products i.e. carbamates in alcohols and N,N′-disubstituted symmetrical urea in THF.
- Singh, Anoop S.,Kumar, Dhananjay,Mishra, Nidhi,Tiwari, Vinod K.
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p. 84512 - 84522
(2016/10/12)
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- Identification of a novel class of quinoline-oxadiazole hybrids as anti-tuberculosis agents
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A series of novel quinoline-oxadiazole hybrid compounds was designed based on stepwise rational modification of the lead molecules reported previously, in order to enhance bioactivity and improve druglikeness. The hybrid compounds synthesized were screened for biological activity against Mycobacterium tuberculosis H37Rv and for cytotoxicity in HepG2 cell line. Several of the hits exhibited good to excellent anti-tuberculosis activity and selectivity, especially compounds 12m, 12o and 12p, showed minimum inhibitory concentration values 500. The results of this study open up a promising avenue that may lead to the discovery of a new class of anti-tuberculosis agents.
- Jain, Puneet P.,Degani, Mariam S.,Raju, Archana,Anantram, Aarti,Seervi, Madhav,Sathaye, Sadhana,Ray, Muktikanta,Rajan
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p. 645 - 649
(2016/01/09)
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- Solid-phase preparation of amides using N-acylbenzotriazoles
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Wang resin linked amines were efficiently converted into amides using acylbenzotriazoles. Cleavage of resins gave the desired amides 7Aa-Gf in 30-99% yields with good to excellent purities.
- Katritzky, Alan R,Rogovoy, Boris V,Kirichenko, Nataliya,Vvedensky, Vladimir
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p. 1809 - 1811
(2007/10/03)
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