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Bioisosterism: Interchange of 4-OH to 4-NH2 in Vanillin or Homovanillin Ring of Capsaicinoids
Cho, Sung-Ju,Jung, Young-Sik,Seong, Churl-Min,Park, Woo-Kyu,Kong, Jae-Yang,Park, No-Sang The Pharmaceutical Society of Korea 1999 Archives of Pharmacal Research Vol.22 No.2
A series of 4-amino Capsaincin anallogs 15, 17 and 19 were prepared to investigate the bioisosteric effect of 4-amino group, and all these compounds exhibited moderate or weak potency from their analgesic test. From our previous results and others, 4-hydroxyl group as well as 3-methoxy substituent could be crucial for high analgesic activity. This biological results also shows that the activity is sensitive to alkyl chain length in hydrophobic region and the phenylacetic amides 19 are more active than the corresponding urea derivatives 17.
Hwang, Ki-Jun,Lee, Tae-Suk,Kim, Ki-Won,Kim, Beam-Tae,Lee, Chul-Min,Park, Eun-Young,Woo, Ran-Sook The Pharmaceutical Society of Korea 2001 Archives of Pharmacal Research Vol.24 No.4
Bioisostere approach has been shown to be useful to augment potency or to modify certain physiological properties of a lead compound. Based upon well documented bioisosterism, an isosteric replacement of benzene ring of 4-hydroxy-2-quinolone compound (L-695902) with a thiophene moiety was carried out to prepare the title compounds, 4-hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b] pyrimidines 15. The resulting bioisosteric compounds 15 were evaluated for their antagonistic activity (birding assay) for NMDA receptor glycine site.
ELSEVIER : Synthesis of novel 5-oxaprotoberberines as bioisosteres of protoberberines
( Yi Feng Jin ),( Daulat Bikram Khadka ),( Su Hui Yang ),( Chao Zhao ),( Won Jea Cho ) 전남대학교 약품개발연구소 2014 약품개발연구지 Vol.23 No.-
5-0xaprotoberberinones and 5-oxaprotoberberinium were synthesized as bioisosteres of protoberberines. 5-0xaprotoberberinones were prepared by linking phenol with the isoquinolone ring of 3-phenoIisoquinoIones by methyleneoxy bridge, while the quaternary 5-oxaprotoberberinium salt was synthesized by reduction and oxidation of the lactam moiety of 5-oxaprotoberberinone. ⓒ 2014 Elsevier Ltd. All rights reserved.
Park, Seol Rin,Kim, Juhyun,Lee, Sun Young,Park, Young-Ho,Kim, Hee-Doo Elsevier 2018 Bioorganic & medicinal chemistry letters Vol.28 No.11
<P><B>Abstract</B></P> <P>In order to replace thiourea group with the more drug-like moiety for 1,3-dibenzylthioureas having TRPV1 antagonist activity, we introduced a set of functional groups between the two aromatic rings based on bioisosteric replacement. The synthesized bioisosteres of 1,3-dibenzylthioureas were tested for their antagonist activities on TRPV1 by <SUP>45</SUP>Ca<SUP>2+</SUP>-influx assay using neonatal rat cultured spinal sensory neurons. Among the tested 14 kinds of bioisosters, 2-methylacrylamide group was the best candidate to replace thiourea group. Compound <B>7c</B>, 2-methylacrylamide analog of ATC-120, showed as potent as ATC-120 in its antagonist activity. In addition, 2-methylacrylamide analog <B>7e</B> having vinyl moiety showed the most potent activity with 0.022 μM of IC<SUB>50</SUB> value, indicating that thiourea group of 1,3-dibenzylthioureas could be replaced to 2-methylacrylamide without loss of their potencies.</P> <P><B>Highlights</B></P> <P> <UL> <LI> 1,3-Dibenzylthioureas having methanesulfonylamide are potent TRPV1 antagonists. </LI> <LI> Thiourea moiety of 1,3-dibenzylthioureas could be replaced to 2-methylacrylamide. </LI> <LI> This replacement enable us to design the more druggable TRPV1 related antagonists. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>
Synthesis and Antiviral Activity of $2^1$-Fluorohexopyranosyl Nucleosides
Jeong, Lak-Shin,Lee, Jong-Eun,Kim, Hea-Ok,Chun, Moon-Woo The Pharmaceutical Society of Korea 1998 Archives of Pharmacal Research Vol.21 No.3
$2^1$-Fluorohexopyranosyl nucleosides 1a and 1b which contained a bioisosteric double bond and a fluorine were synthesized in 12 steps, starting from D-galactose. During diethylaminosulfur trifluoride (DAST) fluorination, retention of stereochemistry was observed through the participation of methoxy or chloro group at the 6-posiition of the purine base. The final nucleosides 1a and 1b were found to be inactive against HIV-1 and HSV-1,2.
정원영(Won Young Jung),마은숙(Eun Sook Ma) 대한약학회 2003 약학회지 Vol.47 No.1
In order to search the new serotonin bioisoster, 2-(5,6-dimethoxy-1-indenyl)ethyl amine(1) was synthesized. 3,4- Dimethoxybenzaldehyde , as starting material, was condensed with masonic acid in the pre sense of pyridine and piperidine to form 3,4- dimethoxycinnamic acid(2). Compound 2 was performed catalytic hydrogenation with 17% Pd-C to give propanoic acid derivative 3, which was cyclized by Friedel-Crafts acylation to afford 5,6-dimethoxyindan-1-one(4). Compound 4 was reduced with NaBH4 in ethanol to obtain 1-indanol 5, and it was dehydrated to give 5,6-dimethoxy-1- indene(6). This compound was lithiate d with 2.5M n-butyllithium and reacted with 1,2-dibromoe thane to give 2- (5,6-dimethoxy-1-indenyl)ethyl bromide(7), and which was treated with anhydrous ammonia to synthesize compound 1.
( Radha Karki ),( Chan Mi Park ),( Kyu Yeon Jun ),( Tara Man Kadayat ),( Eung Seok Lee ),( Young Joo Kwon ) 영남대학교 약품개발연구소 2015 영남대학교 약품개발연구소 연구업적집 Vol.25 No.-
Dihydroxylated 2,4-diphenyl-6-aryl pyridine derivatives were simply achieved using Claisen-Schmidt condensation reaction and mdifiled Krohnke pyridine synthetic method. Total forty-five compounds were designed and synthesized which contain hydroxyl groups at ortho, meta or para position of 2- and 4-phrnyl rings attached to the central pyridine. They were evaluated for topoisomerase I and II inhibitory activity, and cytotoxicity against several human cancer cell lines for the development of novel antitumor agents. Most of the prepared compounds exhibited dignificant antiproliferative activity on human cancer cell lines, HCT15 and K562, as well as potent topo II inhibitory activity comparable to or stronger than etoposide. The structure-activity relationship demonstrated that compounds with hydroxyl group at meta or para position of 2-phenyl ring in combination with htdroxyl at ottho, meta or para position of 4-phenyl ring displayed the most potent topoisomerase II inhibitory activity and cytotoxicity. Posirice correlation between topoisomerase II inhibition and cytotoxicity was obtained for several compounds (30, 35, 36, 40-45, 49, 54, 56). Compound 56 showed the most potent topoisomerase II inhibitory activity at low concentrartion and functioned as a topoisomerase poison like the mode of action of etoposide. ⓒ2014 Elsevier Masson SAS. All rights reserved.