Novel macrocyclic molecules based on 12a-N substituted 16-membered azalides and azalactams as potential antifungal agents.
Novel macrocyclic molecules comprising sulfonyl and acyl moiety at the position N-12a of 16-membered azalides (6a-n) and azalactams (10a-r) scaffold were synthesized from cyclododecanone 1 as starting material via 5 steps and 4 steps, respectively. The antifungal activity of these compounds against Sclerotinia sclerotiorum, Pyricularia oryzae, Botrytis cinerea, Rhizoctonia solani and Phytophthora capsici were evaluated and found that compounds possessing α-exomethylene (6c, 6d, 6e and 6g) showed antifungal activity comparable to commercial fungicide Chlorothalonil against P. oryzae and compounds possessing p-chlorobenzoyl exhibited enhanced antifungal activity than those with other substituents against S. sclerotiorum, P. oryzae, and B. cinerea. These findings suggested that the α-exomethylene and p-chlorobenzoyl may be two potential pharmacological active groups with antifungal activities.
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
Xiaolei
X
Wang
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
Shun
S
Zhang
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
Yanlong
Y
Pang
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
Huihui
H
Yuan
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
Xiaomei
X
Liang
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
Jianjun
J
Zhang
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
Daoquan
D
Wang
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
Mingan
M
Wang
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. Electronic address: dongyh@cau.edu.cn.
Yanhong
Y
Dong
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001203:Ascomycota / Q000187:drug effects / Q000254:growth & development; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D047029:Lactams, Macrocyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D003904:Mitosporic Fungi / Q000187:drug effects / Q000254:growth & development; D015394:Molecular Structure; D025282:Mycelium / Q000187:drug effects / Q000254:growth & development
D000935:Antifungal Agents; D001372:Aza Compounds; D047029:Lactams, Macrocyclic
Antifungal activity; Azalactams; Azalides; Macrocyclic molecules; Synthesis