@article {46429, title = {Efficient and convenient route for the synthesis of thiophene-2-carboxamidines as potential inhibitors of nitric oxide synthase (NOS)}, journal = {Tetrahedron Letters}, volume = {60}, year = {2019}, month = {NOV}, pages = {151254}, type = {Article}, abstract = {

A mild and efficient synthesis of substituted thiophene-2-carboxamidines which are potent inhibitors of nitric oxide synthase (NOS) is reported herein. The key step involves reaction of a BOC-protected imidazolyl thiophene-2-carboxamidine reactive intermediate with various primary amines to form BOC-thio-phene-2-carboxamidines which could be readily deprotected using TFA to furnish free carboxamidines. The method is very mild and tolerates diverse substituents including sensitive peptide and amino acid fragments. This new methodology represents a substantial improvement to the literature method owing to its simplicity and hassle-free purification procedures. (C) 2019 Elsevier Ltd. All rights reserved.

}, keywords = {Amidines, Nitric oxide synthase (NOS), Nitric oxide synthase inhibitors, Thiophene-2-carboxamidines}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2019.151254}, author = {Rashid, P. P. and Singh, Dharmendra and Sanjayan, Gangadhar J.} } @article {46894, title = {Novel cilengitide-based cyclic RGD peptides as alpha nu beta(3) integrin inhibitors}, journal = {Bioorganic \& Medicinal Chemistry Letters}, volume = {30}, year = {2020}, month = {APR}, pages = {127039}, type = {Article}, abstract = {

In this letter, we report a series of five new RGD-containing cyclic peptides as potent inhibitors to alpha nu beta(3) integrin protein. We have incorporated various unnatural lipophilic amino acids into the cyclic RGD framework of cilengitide, which is selective for alpha nu beta(3) integrin. All the newly synthesized cyclic peptides were evaluated in vitro solid phase binding assay and investigated for their binding behaviour towards integrin subtypes. All the cyclic peptides were synthesized in excellent yield following solution-phase coupling strategy. The cyclic RGD peptides 1a-e exhibited IC50 of 9.9, 5.5, 72, 11 and 3.3 nM, respectively, towards a alpha nu beta(3) integrin protein. This finding offers further opportunities for the introduction unusual amino acids into the cyclic peptide framework of cilengitide.

}, keywords = {Anticancer drugs, Cilengitide, Integrins, RGD cyclicpeptides}, issn = {0960-894X}, doi = {10.1016/j.bmcl.2020.127039}, author = {Meena, Chhuttan L. and Singh, Dharmendra and Weinmueller, Michael and Reichart, Florian and Dangi, Abha and Marelli, Udaya Kiran and Zahler, Stefan and Sanjayan, Gangadhar J.} } @article {47064, title = {Triazine-based janus G-C nucleobase as a building block for self-assembly, peptide nucleic acids, and smart polymers}, journal = {Journal of Organic Chemistry}, volume = {86}, year = {2021}, month = {FEB }, pages = {3186-3195}, type = {Article}, abstract = {

This communication reports on the utility of a triazine-based self-assembling system, reminiscent of a Janus G-C nucleobase, as a building block for developing (1) supramolecular polymers, (2) peptide nucleic acids (PNAs), and (3) smart polymers. The strategically positioned self-complementary triple H-bonding arrays DDA and AAD facilitate efficient self-assembly, leading to a linear supramolecular polymer.

}, issn = {0022-3263}, doi = {10.1021/acs.joc.0c02530}, author = {Meena, Chhuttan L. and Singh, Dharmendra and Kizhakeetil, Bhavya and Prasad, Manasa and George, Malini and Tothadi, Srinu and Sanjayan, Gangadhar J.} }