Synthesis, Crystal Structure and Antimicrobial Activity of (E)-2-(2-(4,8,8-Trimethyldecahydro-1,4-methanoazulen-9-ylidene)ethyl)benzo[d]isothiazol-3(2H)-one
蓝虹云;霍尚朝;黄道战;陆于州
a (College of Chemistry and Chemical Engineering,Guangxi University for Nationalities, Nanning 530008, China)
b (Guangxi Key Laboratory of Chemistry and Engineering of Forest Products,Guangxi University for Nationalities, Nanning 530008, China)
Synthesis, Crystal Structure and Antimicrobial Activity of (E)-2-(2-(4,8,8-Trimethyldecahydro-1,4-methanoazulen-9-ylidene)ethyl)benzo[d]isothiazol-3(2H)-one
LAN Hong-Yun;HUO Shang-Chao;HUANG Dao-Zhan;LU Yu-zhou
a (College of Chemistry and Chemical Engineering,Guangxi University for Nationalities, Nanning 530008, China)
b (Guangxi Key Laboratory of Chemistry and Engineering of Forest Products,Guangxi University for Nationalities, Nanning 530008, China)
摘要The title compound (E)-2-(2-(4,8,8-trimethyldecahydro-1,4-methanoazulen-9-ylidene)ethyl)ben- zo[d]isothiazol-3(2H)-one (Ic) was synthesized from longifolene and 1,2-benzoisothiazolinone (short as BIT) through Prins, halogenation and nitro-alkylation reaction and structurally identified by means of HRMS, IR, 1H-NMR, 13C-NMR and single-crystal X-ray diffraction. The crystal of compound Ic is of bi-molecular structure and belongs to orthorhombic system, P212121 space group with a = 7.5715(7), b = 16.8824(9), c = 31.1926(14) Å, V = 3987.2(5) Å3, Mr = 367.53, Dc = 1.225 mg/m3, Z = 8, μ = 0.174 mm–1 and F(000) = 1584. A total of 17045 reflections were collected, of which 7306 were unique (Rint = 0.0566). The structure was refined to R = 0.0967 and wR = 0.1998 for 7306 observed reflections with I > 2σ(I). 1D chain along the a-axis is formed by two types of π-π interactions between benzene rings from adjacent molecules. Especially, compound Ic shows improved solubility in nonpolar organic solvents and higher antimicrobial activity than longifolene and BIT against bacteria and fungi. The minimum inhibition concentration (MIC) of Ic against two Gram-positive bacteria (S. aureus and B. subtili), two Gram-negative bacteria (E. coli and K. pneumoniae) and three fungi (C. albicans, C. tropicalis and A. niger) are 0.242, 0.242, 15.6, 15.6, 1.95, 1.95 and 1.95 µg/mL, respectively.
Abstract：The title compound (E)-2-(2-(4,8,8-trimethyldecahydro-1,4-methanoazulen-9-ylidene)ethyl)ben- zo[d]isothiazol-3(2H)-one (Ic) was synthesized from longifolene and 1,2-benzoisothiazolinone (short as BIT) through Prins, halogenation and nitro-alkylation reaction and structurally identified by means of HRMS, IR, 1H-NMR, 13C-NMR and single-crystal X-ray diffraction. The crystal of compound Ic is of bi-molecular structure and belongs to orthorhombic system, P212121 space group with a = 7.5715(7), b = 16.8824(9), c = 31.1926(14) Å, V = 3987.2(5) Å3, Mr = 367.53, Dc = 1.225 mg/m3, Z = 8, μ = 0.174 mm–1 and F(000) = 1584. A total of 17045 reflections were collected, of which 7306 were unique (Rint = 0.0566). The structure was refined to R = 0.0967 and wR = 0.1998 for 7306 observed reflections with I > 2σ(I). 1D chain along the a-axis is formed by two types of π-π interactions between benzene rings from adjacent molecules. Especially, compound Ic shows improved solubility in nonpolar organic solvents and higher antimicrobial activity than longifolene and BIT against bacteria and fungi. The minimum inhibition concentration (MIC) of Ic against two Gram-positive bacteria (S. aureus and B. subtili), two Gram-negative bacteria (E. coli and K. pneumoniae) and three fungi (C. albicans, C. tropicalis and A. niger) are 0.242, 0.242, 15.6, 15.6, 1.95, 1.95 and 1.95 µg/mL, respectively.
基金资助:Supported by the Natural Science Foundation of Guangxi Zhuang Autonomous Region (No. 2017GXNSFAA198027),Special Fund for Innovation-driven Devlopment of Guangxi (GUIKE AA17204087-21) and National Training Program of Innovation and Entrepreneurship for Undergraduates (201510608042)
通讯作者:
huangdaozhan@gxun.edu.cn and hdz547008601@163.com
E-mail: huangdaozhan@gxun.edu.cn and hdz547008601@163.com
引用本文:
蓝虹云;霍尚朝;黄道战;陆于州. Synthesis, Crystal Structure and Antimicrobial Activity of (E)-2-(2-(4,8,8-Trimethyldecahydro-1,4-methanoazulen-9-ylidene)ethyl)benzo[d]isothiazol-3(2H)-one[J]. 结构化学, 2020, 39(8): 1546-1552.
LAN Hong-Yun;HUO Shang-Chao;HUANG Dao-Zhan;LU Yu-zhou. Synthesis, Crystal Structure and Antimicrobial Activity of (E)-2-(2-(4,8,8-Trimethyldecahydro-1,4-methanoazulen-9-ylidene)ethyl)benzo[d]isothiazol-3(2H)-one. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2020, 39(8): 1546-1552.
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