16892-50-5Relevant academic research and scientific papers
8-THIABICYCLOOCTAN-3-ONE AS A BIOCHEMICAL TOOL IN THE STUDY OF TROPANE ALKALOID BIOSYNTHESIS
Parr, Adrian J.,Walton, Nick J.,Bensalem, Smail,McCabe, Peter H.,Routledge, William
, p. 2607 - 2609 (1991)
8-Thiabicyclooctan-3-one, the sulphur analogue (replacing the methylaza bridge) of tropinone, was fed to Datura stramonium transformed root cultures.The compound was metabolized to a large degree.Notable products included the reduction product, 8-thiabicyclooctan-3-ol, analogous to tropine, and also the derived 3-O-acetyl ester.In addition, tropane alkaloid synthesis was perturbed.Hyoscyamine levels, and in particular tropine and 3α-acetoxytropane levels, were reduced.Pseudotropine, on the other hand, was found to increase in concentration.It is concluded that 8-thiabicyclooctan-3-one may be a good biochemical tool in the study of tropane alkaloid biosynthesis.Key Word Index -Datura stramonium; Solanaceae; biosynthesis; inhibitor; tropanealkaloids; tropine; pseudotropine; 8-thiabicyclooctan-3-one
Studies on enolate chemistry of 8-thiabicyclo[3.2.1]-octan-3-one: Enantioselective deprotonation and synthesis of sulfur analogs of tropane alkaloids
Majewski, Marek,DeCaire, Marc,Nowak, Pawel,Wang, Fan
, p. 1792 - 1798 (2001)
Enantioselective deprotonation of 8-thiabicyclo[3.2.1]octan-3-one (1) with chiral lithium amides, followed by reactions with electrophiles affords sulfur analogs of tropane alkaloids of pyranotropane family. Thus, deprotonation of 1 with (S)-N-(diphenyl)m
Synthesis of 8-thiabicyclo[3.2.1]octanes and their binding affinity for the dopamine and serotonin transporters
Pham-Huu, Duy-Phong,Deschamps, Jeffrey R.,Liu, Shanghao,Madras, Bertha K.,Meltzer, Peter C.
, p. 1067 - 1082 (2007)
Cocaine is a potent stimulant of the central nervous system. Its reinforcing and stimulant properties have been associated with inhibition of the dopamine transporter (DAT) on presynaptic neurons. In the search for medications for cocaine abuse, we have p
Tropane alkaloid metabolism by Pseudomonas AT3 cell cultures: Interchange between the nortropine and norpseudotropine catabolic pathways
Kosieradzka, Katarzyna,Le Faouder, Pauline,Molinié, Roland,Gentil, Emmanuel,Lebreton, Jacques,Robins, Richard J.
, p. lxviii (2014)
Selected strains of Pseudomonas bacteria can degrade tropane alkaloids to obtain both nitrogen and carbon for growth. In order to probe the mechanisms of the catabolic enzymes involved, the metabolic process responsible for the opening of the 8-azabicyclo[3.2.1]octan-3-ol ring of nortropane alkaloids has been explored. It is found that the bacteria contain considerable flexibility in their enzyme complement and can convert (3-endo)-8-azabicyclo[3.2.1]octan-3-ol) (nortropine (2) to (3-exo)-8-azabicyclo[3.2.1]octan-3-ol) (norpseudotropine). Both of these compounds can serve as substrates for the catalytic cascade. In order to establish the proportionation between direct and indirect pathways, metabolism has been probed by competitive substrate availability and by incorporation of stable heavy labels into substrate pools. The results indicate that, while norpseudotropine is almost entirely metabolized directly, nortropine is partitioned c. 4:1 between direct and indirect catabolism.
PHOTOACID GENERATOR, CHEMICALLY AMPLIFIED RESIST COMPOSITION, AND PATTERNING PROCESS
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Paragraph 0224-0225, (2020/02/22)
A photoacid generator having formula (1a) is provided. A chemically amplified resist composition comprising the PAG forms a pattern of rectangular profile with a good balance of sensitivity and LWR when processed by photolithography using ArF excimer lase
3,5-Disubstituted-indole-7-carboxamides as IKKβ Inhibitors: Optimization of Oral Activity via the C3 Substituent
Kerns, Jeffrey K.,Busch-Petersen, Jakob,Fu, Wei,Boehm, Jeffrey C.,Nie, Hong,Muratore, Michael,Bullion, Ann,Lin, Guoliang,Li, Huijie,Davis, Roderick,Lin, Xichen,Lakdawala, Ami S.,Cousins, Rick,Field, Rita,Payne, Jeremy,Miller, David D.,Bamborough, Paul,Christopher, John A.,Baldwin, Ian,Osborn, Ruth R.,Yonchuk, John,Webb, Edward,Rumsey, William L.
supporting information, p. 1164 - 1169 (2018/11/23)
IκB kinase β (IKKβ or IKK2) is a key regulator of nuclear factor kappa B (NF-κB) and has received attention as a therapeutic target. Herein we report on the optimization of a series of 3,5-disubstituted-indole-7-carboxamides for oral activity. In doing so
INDOLE CARBOXAMIDES AS IKK2 INHIBITORS
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Page/Page column 83, (2008/12/04)
The invention is directed to novel indole carboxamide compounds. Specifically, the invention is directed to compounds according to formula (I): wherein R1, R2, R3, R4, and m are as defined herein. The compounds of the invention are inhibitors of IKK2 and can be useful in the treatment of disorders associated with inappropriate IKK2 (also known as IKKβ) activity, such as rheumatoid arthritis, asthma, rhinitis, and COPD (chronic obstructive pulmonary disease). Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting IKK2 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.
SULFIDE EXTRUSION FROM THE METHYLSULFONIUM SALTS OF 8-THIABICYCLO-OCT-2-ENES AND THE RELATED SULFONIUM SALTS BY METHYLLITHIUM
Uyehara, Tadao,Takahashi, Masayuki,Kato, Tadahiro
, p. 3999 - 4002 (2007/10/02)
The methylsulfonium salts of 2-methylene-8-thiabicyclooctane and 8-thiabicyclooct-2-enes underwent sulfide extrusion by methyllithium to give dimethyl sulfide and the hydrogen shift products (cycloheptadienes) and/or the closure products (bi
