DNA-Compatible Cyclization Reaction to Access 1,3,4-Oxadiazoles and 1,2,4-Triazoles

被引：1

作者：

Wang, Gaonan ^{[1
]}

Tan, Yu ^{[1
]}

Zou, Hanzhi ^{[1
]}

Sui, Xihang ^{[1
]}

Wang, Zhanlong ^{[1
]}

Satz, Alexander L. ^{[2
]}

Kuai, Letian ^{[3
]}

Su, Wenji ^{[1
]}

Zhang, Qi ^{[1
]}

机构：

[1] WuXi AppTec, Shanghai 200131, Peoples R China

[2] WuXi AppTec, D-82152 Martinsried, Germany

[3] WuXi AppTec, Cambridge, MA 02142 USA

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 07期

关键词：

D O I：

10.1021/acs.orglett.3c04240

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

DNA-encoded chemical library (DECL) technology is a commonly employed screening platform in both the pharmaceutical industry and academia. To expand the chemical space of DECLs, new and robust DNA-compatible reactions are sought after. In particular, DNA-compatible cyclization reactions are highly valued, as these reactions tend to be atom economical and thus may provide lead- and drug-like molecules. Herein, we report two new methodologies employing DNA-conjugated thiosemicarbazides as a common precursor, yielding highly substituted 1,3,4-oxadiazoles and 1,2,4-triazoles. These two novel DNA-compatible reactions feature a high conversion efficiency and broad substrate scope under mild conditions that do not observably degrade DNA.

引用

页码：1353 / 1357

页数：5

共 50 条

[41] Formal [4+1] cyclization of (thio/imido)hydrazides and ethyl 3,3,3-trifluoropropanoate: unified synthesis of 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazoles
Zhao, Lan
Xu, Jun
Ma, Jun
Yin, Guangwei
Li, Fangyi
Suo, Tongchuan
Wang, Chunhua
NEW JOURNAL OF CHEMISTRY, 2022, 46 (43) : 20755 - 20759
[42] Green synthesis, molecular docking and in vitro biological evaluation of novel hydrazones, pyrazoles, 1,2,4-triazoles and 1,3,4-oxadiazoles
Younis, Ahmed
Kassem, Asmaa F.
Aboulthana, Wael M.
Sediek, Ashraf A.
SYNTHETIC COMMUNICATIONS, 2024, 54 (22) : 1984 - 2002
[43] Synthesis of Amino-1,2,4-triazoles by Reductive ANRORC Rearrangements of 1,2,4-Oxadiazoles
Piccionello, Antonio Palumbo
Guarcello, Annalisa
Buscemi, Silvestre
Vivona, Nicolo
Pace, Andrea
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (24): : 8724 - 8727
[44] A mild approach to 1,3,4-oxadiazoles and fused 1,2,4-triazoles. Diazenes as intermediates?
Kosmrlj, J
Kocevar, M
Polanc, S
SYNLETT, 1996, (07) : 652 - &
[45] Syntheses of 5-(2-arylazenyl)-1,2,4-triazoles and 2-Amino-5-aryl-1,3,4-oxadiazoles
Katritzky, AR
Vvedensky, V
Cai, XH
Rogovoy, B
Steel, PJ
ARKIVOC, 2002, : 82 - 90
[46] Synthesis, reactions and antimicrobial activity of some new 1,3,4-oxadiazoles, 1,2,4-triazoles and 1,3,4-thiadiazines derived from pyrazole.
Farghaly, AA
Vanelle, P
El-Kashef, HS
HETEROCYCLIC COMMUNICATIONS, 2005, 11 (3-4) : 255 - 262
[47] Synthesis, analgesic and anti-inflammatory activities of new methyl-imidazolyl-1,3,4-oxadiazoles and 1,2,4-triazoles
Ali Almasirad
Zahra Mousavi
Mohammad Tajik
Mohammad Javad Assarzadeh
Abbas Shafiee
DARU Journal of Pharmaceutical Sciences, 22
[48] Synthesis and anti-Helicobacter pylori activity of (4-nitro-1-imidazolylmethyl)-1,2,4-triazoles, 1,3,4-thiadiazoles, and 1,3,4-oxadiazoles
Tafti, Asal Fallah
Akbarzadeh, Tahmineh
Saniee, Parastoo
Siavoshi, Farideh
Shafiee, Abbas
Foroumadi, Alireza
TURKISH JOURNAL OF CHEMISTRY, 2011, 35 (02) : 307 - 316
[49] Synthesis, analgesic and anti-inflammatory activities of new methyl-imidazolyl-1,3,4-oxadiazoles and 1,2,4-triazoles
Almasirad, Ali
Mousavi, Zahra
Tajik, Mohammad
Assarzadeh, Mohammad Javad
Shafiee, Abbas
DARU-JOURNAL OF PHARMACEUTICAL SCIENCES, 2014, 22
[50] Synthesis of a New Class of Sulfonamido Bis Heterocycles-Pyrrolyl/Pyrazolyl-1,3,4-oxadiazoles, 1,3,4-Thiadiazoles, and 1,2,4-Triazoles
Muralikrishna, Akkarapalli
Reddy, Guda Mallikarjuna
Lavanya, Gopala
Padmavathi, Venkatapuram
Padmaja, Adivireddy
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (01) : 179 - 190

← 1 2 3 4 5 →