Synthesis of 1,2,3-Triazole Analogues of Lincomycin

被引：25

作者：

Collin, Marie-Pierre ^{[1
]}

Hobbie, Sven N. ^{[2
]}

Boettger, Erik C. ^{[2
]}

Vasella, Andrea ^{[1
]}

机构：

[1] ETH, Organ Chem Lab, Dept Chem & Angew Biowissensch, HCI Honggerberg, CH-8093 Zurich, Switzerland

[2] Univ Zurich, Inst Med Mikrobiol, CH-8006 Zurich, Switzerland

来源：

HELVETICA CHIMICA ACTA | 2008年 / 91卷 / 10期

关键词：

D O I：

10.1002/hlca.200890196

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In search for ne v antibiotics we replaced the amide moiety of lincomycin I by a 1,23-triazole ring. The 1.2,3-triazoles 10a-10k were obtained as single regioisomers by 'click reaction' of azide 5 with the alkyne 9k, derived from propyl hygric acid, and the alkyl, aryl, or cycloalkyl alkynes ribosomes 9a-9j. The new analogues proved inactive towards wild-type and A2058G mutant.

引用

页码：1838 / 1848

页数：11

共 50 条

[1] Synthesis of 1,2,3-Triazole Nucleoside Analogues
Yu, Pan
Liu, Ningning
Yuan, Weiyuan
Wen, Yining
Wu, Qinpei
[J]. PROCEEDINGS OF THE 2015 INTERNATIONAL CONFERENCE ON INDUSTRIAL TECHNOLOGY AND MANAGEMENT SCIENCE (ITMS 2015), 2015, 34 : 1090 - 1092
[2] Synthesis of 1,2,3-triazole 'click' analogues of thalidomide
Ronnebaum, Jarrid M.
Luzzio, Frederick A.
[J]. TETRAHEDRON, 2016, 72 (40) : 6136 - 6141
[3] 1,2,3-TRIAZOLE ANALOGUES OF 2-AMINOBENZYLAMINE
ALBERT, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1970, (14): : 858 - &
[4] Synthesis and antifungal activity of 1,2,3-triazole containing fluconazole analogues
Aher, Nilkanth G.
Pore, Vandana S.
Mishra, Nripendra N.
Kumar, Awanit
Shukla, Praveen K.
Sharma, Aanchal
Bhat, Manoj K.
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (03) : 759 - 763
[5] Synthesis and evaluation of 1,2,3-triazole containing analogues of the immunostimulant α-GalCer
Lee, Taeho
Cho, Minjae
Ko, Sung-Youl
Youn, Hyun-Jun
Baek, Dong Jae
Cho, Won-Jea
Kang, Chang-Yuil
Kim, Sanghee
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (03) : 585 - 589
[6] Synthesis and Characterization of Azido-Functionalized 1,2,3-Triazole and Fused 1,2,3-Triazole
Cao, Yupeng
Huang, Haifeng
Wang, Limin
Lin, Xiangyang
Yang, Jun
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (07): : 4301 - 4308
[7] Synthesis and Characterization of Azido-Functionalized 1,2,3-Triazole and Fused 1,2,3-Triazole
Cao, Yupeng
Huang, Haifeng
Wang, Limin
Lin, Xiangyang
Yang, Jun
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2023,
[8] SYNTHESIS OF 1,2,3-TRIAZOLE DERIVATIVES
CARBONI, S
DASETTIMO, A
FERRARINI, PL
LIVI, O
TONETTI, I
[J]. CHIMICA & L INDUSTRIA, 1976, 58 (12): : 878 - 878
[9] Synthesis of 1,2,3-Triazole Derivatives
Jiang Yubo
Kuang Chunxiang
[J]. PROGRESS IN CHEMISTRY, 2012, 24 (10) : 1983 - 1994
[10] Synthesis of new 1,2,3-triazole acyclonucleoside analogues of ACV and HBG.
Lazrek, HB
Taourirte, M
Oulih, T
Lebtoumi, M
Barascut, JL
Imbach, JL
[J]. NUCLEOSIDES & NUCLEOTIDES, 1997, 16 (7-9): : 1115 - 1118

← 1 2 3 4 5 →