- Design, synthesis and evaluation of thiazole based amides for their antitubercular and PknG inhibitory activity
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A series of thiazole based amides have been designed and synthesized by solution-phase amide coupling of 2-aminothiazole and its derivatives with naturally occurring aromatic and heteroaromatic acids in excellent yield via DIC/HOBt protocol All the compounds have been evaluated for their antitubercular activity against M. tuberculosis virulent strain M. tuberculosis H37Rv and PknG inhibitory activity in the presence and absence of the inhibitors The compounds display moderate to significant PknG inhibitory activity (9.1-15.6% inhibition at 100 μM) as compared to the standard inhibitors and very moderate in vitro antitubercular activities against M. tuberculosis virulent strain M. tuberculosis H37Rv.
- Sharma, Anindra
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p. 624 - 632
(2021/09/28)
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- Synthesis of a series of benzothiazole amide derivatives and their biological evaluation as potent hemostatic agents
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A series of benzothiazole amide derivatives were synthesized through a facile and efficient method via a nucleophilic acyl substitution reaction between 2-aminobenzothiazole and various cinnamic acid compounds. The obtained products exhibited good thermal stabilities. All compounds were evaluated for their in vitro hemostatic activities using the commercially available standard drug etamsylate as a positive control. The results showed that compound Q2 had a significant partial coagulation activity, reduced capillary permeability at 5, 10 and 50 μmol L-1, activated thrombin activity, and a more potent platelet aggregation activity than the positive control group (etamsylate, up to 1283.9 times in the nanomole range). A molecular modeling study revealed that compound Q2 was a competitive thrombin activator. Therefore, Q2 may be a potential lead for further biological screening and for the generation of drug molecules. Moreover, the structure-activity relationship of the prepared compounds is also discussed herein.
- Nong, Wenqian,Zhao, Anran,Wei, Jinrui,Cheng, Hui,Luo, Xuan,Lin, Cuiwu
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p. 6231 - 6241
(2018/02/19)
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- Access to Amide from Aldimine via Aerobic Oxidative Carbene Catalysis and LiCl as Cooperative Lewis Acid
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Herein, an efficient route to amides from aldimines via aza-Breslow intermediates through aerobic oxidative carbene catalysis with LiCl as a cooperative Lewis acid is described. Many of the obtained N-heteroarylamides feature biological activity. Ambient
- Wang, Guanjie,Fu, Zhenqian,Huang, Wei
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supporting information
p. 3362 - 3365
(2017/07/13)
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- Facile synthesis of N-acyl 2-aminobenzothiazoles by NHC-catalyzed direct oxidative amidation of aldehydes
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A mild, general, and high yielding synthesis of N-acyl 2-aminobenzothiazoles has been demonstrated by N-heterocyclic carbene (NHC)-organocatalyzed direct amidation of aldehydes with 2-aminobenzothiazoles proceeding via acyl azolium intermediates. The carbene generated from the triazolium salt under oxidative conditions was the key for the success of this reaction. The method was subsequently applied to the synthesis of various biologically important N-acyl 2-aminobenzothiazoles.
- Premaletha, Sethulekshmy,Ghosh, Arghya,Joseph, Sumi,Yetra, Santhivardhana Reddy,Biju, Akkattu T.
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supporting information
p. 1478 - 1481
(2017/02/05)
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- Synthesis and Antioxidant Activity of Amido-Linked Benzoxazolyl/Benzothiazolyl/Benzimidazolyl-Pyrazoles and Isoxazoles
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A new class of amido-linked bis heterocycles-benzoxazolyl/benzothiazolyl/benzimidazolyl-pyrazoles and isoxazoles were prepared from benzoxazolyl /benzothiazolyl/benzimidazolyl-cinnamamides and tested for antioxidant activity.
- Durgamma, Suram,Reddy, Putta Ramachandra,Padmavathi, Venkatapuram,Padmaja, Adivireddy
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p. 738 - 747
(2016/05/19)
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- Aerobic Copper-Mediated Domino Three-Component Approach to 2-Aminobenzothiazole Derivatives
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An unprecedented three-component reaction involving a 2,2′-diaminodiaryl disulfide, copper cyanide, and an electrophile is described. This transformation is based on an oxidative copper-mediated S-cyanation as a key step and involves a cyanation/cyclization/acylation domino sequence enabling a rapid and efficient synthesis of diversely substituted 2-aminobenzothiazole derivatives. Notably, this reaction proceeds via an original mechanism involving an intermolecular migration of the acyl group.
- Castanheiro, Thomas,Suffert, Jean,Gulea, Mihaela,Donnard, Morgan
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supporting information
p. 2588 - 2591
(2016/06/15)
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- Imidazolium-supported benzotriazole: an efficient and recoverable activating reagent for amide, ester and thioester bond formation in water
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An efficient and recyclable imidazolium-supported benzotriazole reagent (Im-CH2-BtH) as a novel synthetic auxiliary has been synthesized and its utility as a carboxyl group activating reagent via the formation of stable imidazolium-supported acyl benzotriazoles was explored for the synthesis of amides, esters and thioesters in water under microwave conditions. The reagent was reused five times without any noticeable loss in activity. It is moisture insensitive and highly stable under thermal and aerobic conditions. The application of imidazolium-supported N-acetyl benzotriazole leads to synthesis of paracetamol on the gram scale under greener conditions in 93% yield.
- Shakoor, S.M. Abdul,Choudhary, Sunita,Bajaj, Kiran,Muthyala, Manoj Kumar,Kumar, Anil,Sakhuja, Rajeev
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p. 82199 - 82207
(2015/10/12)
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- Synthesis and antioxidant activity of amido-linked benzoxazolyl/ benzothiazolyl/benzimidazolyl-pyrroles and pyrazoles
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The amido-linked benzoxazolyl/benzothiazolyl/benzimidazolyl-pyrroles and benzoxazolyl/benzothiazolyl/benzimidazolyl-pyrazoles were prepared from the synthetic intermediates (E)-N-(benzoxazol-2-yl)cinnamamide/(E)-N-(benzothiazol- 2-yl)cinnamamide/(E)-N-(1H
- Durgamma, Suram,Muralikrishna, Akkarapalli,Padmavathi, Venkatapuram,Padmaja, Adivireddy
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p. 2916 - 2929
(2014/05/06)
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- Synthesis of novel cinnamoyl amides using a solvent-free microwave-assisted method
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A novel series of potential biologically active new cinnamoyl amides were synthesized in good yield and short reaction times. We have studied the one-pot, solvent-free reaction of cinnamic acid derivatives with aromatic amines using 1,3-dicyclohexylcarbodiimide under microwave irradiation in the presence of small quantities of dimethylformamide to improve energy transfer.
- Pellon, Rolando F.,Docampo, Maite L.
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p. 537 - 552
(2013/01/15)
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- CORRELATION OF STRUCTURAL PARAMETERS WITH ANTITUBERCULOTIC ACTIVITY IN A GROUP OF 2-BENZAMIDOBENZOTHIAZOLES
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Fourteen 2-benzamidobenzothiazole derivatives substituted in the benzoyl group and 2-cinnamamidobenzothiazole have been synthetized.The prediction of active structures by the method by Topliss gives incorrect results but, as shown on the basis of the Hans
- Waisser, Karel,Kunes, Jiri,Odlerova, Zelmira
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p. 2978 - 2985
(2007/10/02)
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- New Synthesis of Dimethyl-cinnamoylimino-dithiocarboxylate and Reactions with Nucleophiles
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A new general synthesis of dimethyl-cinnamoylimino-dithiocarboxylate 1d is possible by reaction of 4-nitro-cinnamoylamide with carbon disulfide in the presence of sodium hydride and following alkylation.With the unsubstituted dimethyl-cinnamoylimino-dithi
- Richter, M.,Herrmann, C.,Augustin, M.
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p. 434 - 444
(2007/10/02)
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