100817-90-1Relevant articles and documents
An insight into the photophysical properties of amide hydrogen bonded N-(benzo[d]thiazol-2-yl) acetamide crystals
Balijapalli, Umamahesh,Udayadasan, Sathiskumar,Panyam Muralidharan, Vivek,Sukumarapillai, Dileep Kumar,Shanmugam, Easwaramoorthi,Paduthapillai Gopal, Aravindan,Rathore, Ravindranath S.,Kulathu Iyer, Sathiyanarayanan
, p. 572 - 577 (2017)
Three distinct, hydrogen bond associated N-(benzo[d]thiazol-2-yl) acetamides were synthesized by refluxing benzothiazoles with acetic acid. The nature of the assemblies was characteristic to the substituent in the benzothiazole moiety. In N-(benzo[d]thiazol-2-yl)acetamide, water acts as a bridge for forming three hydrogen bonds, as an acceptor to amide N[sbnd]H, and donors to carbonyl of amide and thiazole nitrogen assembles of three different N-(benzo[d]thiazol-2-yl)acetamide molecules. The N-(6-methylbenzo[d]thiazol-2-yl)acetamide formed a (amide) N-H…N (thiazole) bonded R22(8) molecular dimers by two homo-intermolecular hydrogen bonding interactions. N-(6-methoxybenzo[d]thiazol-2-yl)acetamide formed (amide)N-H…O (acid) & (acid)O-H…N (thiazole) interactions with the acetic acid, forming a R22(8) hydrogen-bonded ring by two hetero-intermolecular hydrogen bonding interactions.
Probing the ATP-Binding Pocket of Protein Kinase DYRK1A with Benzothiazole Fragment Molecules
Rothweiler, Ulli,Stensen, Wenche,Brandsdal, Bj?rn Olav,Isaksson, Johan,Leeson, Frederick Alan,Engh, Richard Alan,Svendsen, John S. Mj?en
, p. 9814 - 9824 (2016/11/19)
DYRK1A has emerged as a potential target for therapies of Alzheimer's disease using small molecules. On the basis of the observation of selective DYRK1A inhibition by firefly d-luciferin, we have explored static and dynamic structural properties of fragment sized variants of the benzothiazole scaffold with respect to DYRK1A using X-ray crystallography and NMR techniques. The compounds have excellent ligand efficiencies and show a remarkable diversity of binding modes in dynamic equilibrium. Binding geometries are determined in part by interactions often considered "weak", including "orthogonal multipolar" types represented by, for example, F-CO, sulfur-aromatic, and halogen-aromatic interactions, together with hydrogen bonds that are modulated by variation of electron withdrawing groups. These studies show how the benzothiazole scaffold is highly promising for the development of therapeutic DYRK1A inhibitors. In addition, the subtleties of the binding interactions, including dynamics, show how full structural studies are required to fully interpret the essential physical determinants of binding.
Synthesis of N-benzothiazol-2-yl-amides by an iron-catalyzed oxidative C(sp2)-H functionalization
Wang, Junke,Zong, Yingxiao,Zhang, Xuexin,Gao, Yang,Li, Zhengliang,Yue, Guoren,Quan, Zhengjun,Wang, Xicun
, p. 2143 - 2148 (2014/11/08)
Catalytic synthesis of N-benzothiazol-2-yl-amides from 1-acyl-3-(phenyl) thioureas was achieved in the presence of an iron catalyst through C(sp 2)-H functionalization and C-S bond formation. Various N-benzothiazol-2-yl-amides were selectively obtained in good yields. Georg Thieme Verlag Stuttgart, New York.
