PMID- 28551587
OWN - NLM
STAT- MEDLINE
DCOM- 20170926
LR  - 20170926
IS  - 1768-3254 (Electronic)
IS  - 0223-5234 (Linking)
VI  - 136
DP  - 2017 Aug 18
TI  - Efficient click chemistry towards fatty acids containing 1,2,3-triazole: Design 
      and synthesis as potential antifungal drugs for Candida albicans.
PG  - 596-602
LID - S0223-5234(17)30362-8 [pii]
LID - 10.1016/j.ejmech.2017.05.001 [doi]
AB  - Candida is an important opportunistic human fungal pathogen. The cis-2-dodecenoic 
      acid (BDSF) showing in vitro activity of against C. albicans growth, germ-tube 
      germination and biofilm formation has been a potential inhibitor for Candida and 
      other fungi. In this study, facile synthetic strategies toward a novel family of 
      BDSF analogue, 1-alkyl-1H-1,2,3-triazole-4-carboxylic acids (ATCs) was developed. 
      The straightforward synthetic method including converting the commercial 
      available alkyl bromide to alkyl azide, consequently with a typical click 
      chemistry method, copper(II) sulfate and sodium ascorbate as catalyst in water to 
      furnish ATCs with mild to good yields. According to antifungal assay, 
      1-decyl-4,5-dihydro-1H-1,2,3-triazole-4-carboxylic acid (5d) showed antifungal 
      capability slightly better than BDSF. The 1,2,3-triazole unit played a crucial 
      role for the bioactivity of ATCs was also confirmed when compared with two 
      alkyl-aromatic carboxylic acids. Given its simplicity, high antifungal activity, 
      and wide availability of compounds with halide atoms on the end part of the alkyl 
      chains, the method can be extended to develop more excellent ATC drugs for 
      accomplishing the challenges in future antifungal applications.
CI  - Copyright (c) 2017 Elsevier Masson SAS. All rights reserved.
FAU - Fu, Nina
AU  - Fu N
AD  - Key Laboratory for Organic Electronics and Information Displays & Institute of 
      Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for 
      Advanced Materials (SICAM), Nanjing University of Posts & Telecommunications, 9 
      Wenyuan Road, Nanjing 210023, China.
FAU - Wang, Suiliang
AU  - Wang S
AD  - Key Laboratory for Organic Electronics and Information Displays & Institute of 
      Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for 
      Advanced Materials (SICAM), Nanjing University of Posts & Telecommunications, 9 
      Wenyuan Road, Nanjing 210023, China.
FAU - Zhang, Yuqian
AU  - Zhang Y
AD  - Key Laboratory for Organic Electronics and Information Displays & Institute of 
      Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for 
      Advanced Materials (SICAM), Nanjing University of Posts & Telecommunications, 9 
      Wenyuan Road, Nanjing 210023, China.
FAU - Zhang, Caixia
AU  - Zhang C
AD  - Key Laboratory for Organic Electronics and Information Displays & Institute of 
      Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for 
      Advanced Materials (SICAM), Nanjing University of Posts & Telecommunications, 9 
      Wenyuan Road, Nanjing 210023, China.
FAU - Yang, Dongliang
AU  - Yang D
AD  - Key Laboratory for Organic Electronics and Information Displays & Institute of 
      Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for 
      Advanced Materials (SICAM), Nanjing University of Posts & Telecommunications, 9 
      Wenyuan Road, Nanjing 210023, China.
FAU - Weng, Lixing
AU  - Weng L
AD  - School of Geography and Biological Information, Nanjing University of Posts & 
      Telecommunications, 9 Wenyuan Road, Nanjing 210023, China.
FAU - Zhao, Baomin
AU  - Zhao B
AD  - Key Laboratory for Organic Electronics and Information Displays & Institute of 
      Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for 
      Advanced Materials (SICAM), Nanjing University of Posts & Telecommunications, 9 
      Wenyuan Road, Nanjing 210023, China. Electronic address: iambmzhao@njupt.edu.cn.
FAU - Wang, Lianhui
AU  - Wang L
AD  - Key Laboratory for Organic Electronics and Information Displays & Institute of 
      Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for 
      Advanced Materials (SICAM), Nanjing University of Posts & Telecommunications, 9 
      Wenyuan Road, Nanjing 210023, China. Electronic address: iamlhwang@njupt.edu.cn.
LA  - eng
PT  - Journal Article
DEP - 20170502
PL  - France
TA  - Eur J Med Chem
JT  - European journal of medicinal chemistry
JID - 0420510
RN  - 0 (Antifungal Agents)
RN  - 0 (Fatty Acids)
RN  - 0 (Triazoles)
SB  - IM
MH  - Antifungal Agents/chemical synthesis/chemistry/*pharmacology
MH  - Candida albicans/*drug effects
MH  - Click Chemistry
MH  - Dose-Response Relationship, Drug
MH  - *Drug Design
MH  - Fatty Acids/chemical synthesis/chemistry/*pharmacology
MH  - Microbial Sensitivity Tests
MH  - Molecular Structure
MH  - Structure-Activity Relationship
MH  - Triazoles/chemistry/*pharmacology
OTO - NOTNLM
OT  - 1H-1,2,3-triazole
OT  - Antifungal agents
OT  - BDSF analogue
OT  - Candida albicans
OT  - Click chemistry
EDAT- 2017/05/30 06:00
MHDA- 2017/09/28 06:00
CRDT- 2017/05/29 06:00
PHST- 2017/02/25 00:00 [received]
PHST- 2017/04/10 00:00 [revised]
PHST- 2017/05/01 00:00 [accepted]
PHST- 2017/05/30 06:00 [pubmed]
PHST- 2017/09/28 06:00 [medline]
PHST- 2017/05/29 06:00 [entrez]
AID - S0223-5234(17)30362-8 [pii]
AID - 10.1016/j.ejmech.2017.05.001 [doi]
PST - ppublish
SO  - Eur J Med Chem. 2017 Aug 18;136:596-602. doi: 10.1016/j.ejmech.2017.05.001. Epub 
      2017 May 2.