85750-08-9Relevant academic research and scientific papers
Microwave-assisted synthesis of 1,3-benzothiazol-2(3 H)-one derivatives and analysis of their antinociceptive activity
?nkol,Dündar,Yldrm,Erol,?ahin
, p. 571 - 575 (2013/02/23)
A rapid and efficient method was developed for synthesis of 6-acyl-1,3-benzothiazol-2(3H)-one derivatives under microwave irradiation (MWI) conditions. The reaction times were shortened compared to conventional heating. Additionally, we synthesized acetic acid and acetamide derivatives of 1,3-benzothiazol-2(3H)-one, 6-acyl-1,3-benzothiazol-2(3H)-one, 5-chloro-1,3-benzothiazol-2(3H)-one and 6-acyl-5-chloro-1,3-benzothiazol-2(3H)- one with the microwave-assisted method and analyzed their antinociceptive activity with the tail flick, tail clip, hot plate and writhing tests. Among the synthesized compounds, 3-[2-(4-ethylpiperazin-1-yl)-2-oxoethyl]-1,3- benzothiazol-2(3H)-one (6a), 5-chloro-3-{2-oxo-2-[4-(propan-2-yl) piperazin-1-yl]ethyl}-1,3-benzothiazol-2(3H)-one (7e) and 3-[2-(4- butylpiperazin-1-yl)-2-oxoethyl]-5-chloro-1,3-benzothiazol-2(3H)-one (8e) showed significant antinociceptive activity in the tail clip, tail flick, hot plate and writhing tests. Supporting Information available online at http://www.thieme-connect.de/ejournals/toc/amf.
Development of potent and selective small-molecule human Urotensin-II antagonists
McAtee, John J.,Dodson, Jason W.,Dowdell, Sarah E.,Girard, Gerald R.,Goodman, Krista B.,Hilfiker, Mark A.,Sehon, Clark A.,Sha, Deyou,Wang, Gren Z.,Wang, Ning,Viet, Andrew Q.,Zhang, Daohua,Aiyar, Nambi V.,Behm, David J.,Carballo, Luz H.,Evans, Christopher A.,Fries, Harvey E.,Nagilla, Rakesh,Roethke, Theresa J.,Xu, Xiaoping,Yuan, Catherine C.K.,Douglas, Stephen A.,Neeb, Michael J.
scheme or table, p. 3500 - 3503 (2009/04/16)
This work describes the development of potent and selective human Urotensin-II receptor antagonists starting from lead compound 1, (3,4-dichlorophenyl)methyl{2-oxo-2-[3-phenyl-2-(1-pyrrolidinylmethyl)-1-piperidinyl]ethyl}amine. Several problems relating to oral bioavailability, cytochrome P450 inhibition, and off-target activity at the kappa opioid receptor and cardiac sodium channel were addressed during lead development. hUT binding affinity relative to compound 1 was improved by more than 40-fold in some analogs, and a structural modification was identified which significantly attenuated both off-target activities.
Synthesis of 2-Oxo-3-benzothiazolineacetyl Chloride (7), 5-Chloro-2-oxo-3-benzothiazolineacetyl Chloride (8) and Derivatives
D'Amico, John J.,Bollinger, Frederick G.
, p. 1183 - 1190 (2007/10/02)
The reaction of 2-oxo-3-benzothiazolineacetic acid (5) and the 5-chloro analogue 6 with thionyl chloride afforded the titled compounds 7 and 8.The reaction of 7 or 8 with substituted hydrazines, amines or substituted anilines, alcohols and mercaptans furnished the hydrazides 9-14, acetamides and acetanilides 16-21, esters 26-30 and thiolesters 31-37, respectively.Alternate routes for the synthesis of hydrazide 15, acetamides and acetanilides 22-25 and thiolesters 35-36 are described.The reaction of 2-oxo-3(2H)-benzothiazolineacetonitrile with thioacetic acid under acidic conditions afforded 2-oxo-3-benzothiazolineethanethioamide (38).
Use of benzothiazoline compounds as plant growth regulants
-
, (2008/06/13)
Certain benzothiazoline compounds are found to have plant growth regulation activity on leguminous plants.
