Citation: Hong-Yun LAN, Shang-Chao HUO, Dao-Zhan HUANG, Yu-zhou LU. 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]. Chinese Journal of Structural Chemistry, ;2020, 39(8): 1546-1552. doi: 10.14102/j.cnki.0254–5861.2011–2688 shu

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

Hong-Yun LAN ^{a, b} ,
Shang-Chao HUO ^a ,
Dao-Zhan HUANG ^{a, b,,} ,
Yu-zhou LU ^a

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

Corresponding author: Dao-Zhan HUANG, huangdaozhan@gxun.edu.cn; hdz547008601@163.com
Received Date: 2 August 2019
Accepted Date: 13 March 2020

Fund Project: the Natural Science Foundation of Guangxi Zhuang Autonomous Region 2017GXNSFAA198027Special Fund for Innovation-driven Devlopment of Guangxi GUIKE AA17204087-21National Training Program of Innovation and Entrepreneurship for Undergraduates 201510608042

Figures(3)

The title compound (E)-2-(2-(4, 8, 8-trimethyldecahydro-1, 4-methanoazulen-9-ylidene)ethyl)benzo[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, M_r = 367.53, D_c = 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 (R_int = 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.
- longifolene,
- ω-chloromethyl longifolene,
- 1,2-benzoisothiazolinone derivative,
- crystal structure,
- antimicrobial activity
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