3028-06-6Relevant articles and documents
Eco-friendly, catalyst and solvent-free, synthesis of acetanilides and N-benzothiazole-2-yl-acetamides
Cunha, Silvio,De Santana, Louren?o L. B.
, p. 1137 - 1144 (2017/05/01)
An expeditious and green synthesis of acetamides in a solvent-free simple way is described, without catalyst or additives, and in good yield by an instantaneous reaction of anilines or 2-aminothiazoles and acetic anhydride without external heating, and with simple purification. Sixteen substituted acetanilides and four N-benzothiazole-2-yl-acetamides were formed, but aliphatic amines of low molecular weight were not as effective as aromatic ones, and only cyclohexylamine and the enaminone ethyl 3-amino-2-butenoate afforded the corresponding acetamides in good yield.
Reagent-controlled regiodivergent intermolecular cyclization of 2-aminobenzothiazoles with β-ketoesters and β-ketoamides
Roslan, Irwan Iskandar,Ng, Kian-Hong,Chuah, Gaik-Khuan,Jaenicke, Stephan
, p. 2739 - 2750 (2018/01/17)
Two regiodivergent approaches to intermolecular cyclization of 2-aminobenzothiazoles with β-ketoesters and amides have been developed, controlled by the reagents employed. With the Br?nsted base KOt-Bu and CBrCl3 as radical initiator, benzo[d]imidazo[2,1-b]thiazoles are synthesized via attack at the α-carbon and keto carbon of the β-ketoester moiety. In contrast, switching to the Lewis acid catalyst, In(OTf)3, results in the regioselective nucleophilic attack at both carbonyl groups forming benzo[4,5]thiazolo[3,2-a]pyrimidin-4-ones instead.
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 (2016/11/09)
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.
Neurodegenerative Therapies
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Paragraph 0086; 0090; 0091, (2017/01/26)
The present invention provides a compound of formula (I) wherein: Y represents a C or N atom which may be substituted or form a cyclic group with R′″ but may not be a quaternary C atom; R′ is —OR1, —CONH2, —CF3, F, —OH, —NO2, —CN or —OCOR1 in which R1, is C1-3 alkyl and each may be in the beta or gamma position; R″ is C1-3 alkyl or H; and R′″ is H or a group consisting of 1-12 non-hydrogen atoms and may be linear, branched and/or incorporate one or more cyclic groups, cyclic groups may be aromatic and/or heterocyclic and 2 or more cyclic groups may be linked or fused and each may be substituted; or a salt, hydrate or solvate of a compound of formula (I) for use in the treatment or prevention of a neurodegenerative disorder by inhibiting formation of neurofibrillary (tau) tangles and/or by inhibiting Dyrk 1A. The invention further relates to non-therapeutic uses of these compounds.
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 Pd-catalyzed C(sp2)-H functionalization
Wang, Jun-Ke,Zong, Ying-Xiao,Wang, Xi-Cun,Hu, Yu-Lai,Yue, Guo-Ren
, p. 1376 - 1380 (2015/10/28)
A catalytic synthesis of N-benzothiazol-2-yl-amides from 1-acyl-3-(phenyl)thioureas was achieved in the presence of a palladium catalyst through the C(sp2)-H functionalization/C-S bond formation. This synthetic methodology can produce various N
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.
Novel solid-phase parallel synthesis of N-substituted-2-aminobenzo [d]thiazole derivatives via cyclization reactions of 2-iodophenyl thiourea intermediate resin
Kim, Seul-Gi,Jung, Se-Lin,Lee, Gee-Hyung,Gong, Young-Dae
, p. 29 - 40 (2013/03/13)
A novel solid-phase methodology has been developed for the synthesis of N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole derivatives. The key step in this procedure involves the preparation of polymer-bound 2-aminobenzo[d]thiazole resins 5 by cyclization reaction of 2-iodophenyl thiourea resin 3. The resin-bound 2-iodophenyl thiourea 3 is produced by addition of 2-iodophenyl isothiocyanate 2 to the amine-terminated linker amide resin 1. These core skeleton 2-aminobenzo[d]thiazole resins 5 undergo functionalization reactions with various electrophiles, such as alkyl halides, acid chlorides, and sulfonyl chlorides to generate N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole resins 6, 7, and 8, respectively. Finally, N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole derivatives 9, 10, and 11 are then generated in good yields and purities by cleavage of the respective resins 6, 7, and 8 using trifluoroacetic acid (TFA) in dichloromethane (DCM).
Synthesis, anticonvulsant activity and 3D-QSAR study of some prop-2-eneamido and 1-acetyl-pyrazolin derivatives of aminobenzothiazole
Amnerkar, Nikhil D.,Bhusari, Kishore P.
scheme or table, p. 149 - 159 (2010/03/30)
A series of 6-substituted-[3-substituted-prop-2-eneamido]benzothiazole 9-32 and 6-substituted-2-[(1-acetyl-5-substituted)-2-pyrazolin-3-yl]aminobenzothi azole 33-56 were synthesized using appropriate synthetic route and evaluated experimentally against ma
Synthesis of N-benzothiazol-2-yl-amides by a copper-catalyzed intramolecular cyclization process
Wang, Junke,Peng, Feng,Jiang, Ju-li,Lu, Zhi-jin,Wang, Le-yong,Bai, Junfeng,Pan, Yi
, p. 467 - 470 (2008/09/17)
Employing N-(4,5-dihydrooxazol-2-yl)benzamide as novel and efficient ligand, the copper-catalyzed intramolecular cyclization of various substituted 1-acyl-3-(2-bromophenyl)thioureas could be successfully carried out under mild conditions. A variety of N-b
