Abstract
In the title compound, C14H14N2S3, the double-bond system of the acrylo-nitrile moiety is significantly non-planar, with absolute cis torsion angles of 13.9 (2) and 15.1 (2)°. The ring system and the double bond system subtend an inter-planar angle of 11.16 (4)°. The wide angle C-C(CN)=C of 129.40 (12)° may be associated with a balance between planarity and avoidance of a very short S⋯S contact.
Highlights
Research into medicinal chemistry based on benzothiazoles has become a fast developing and progressively more active topic
A large number of therapeutic agents based on benzothiazole systems have been synthesized and evaluated in terms of their pharmacological properties (Gill et al, 2015; Fathy et al, 1988)
Much information about benzothiazoles has been reported in the scientific literature, describing their anti-inflammatory, antimicrobial, neuroprotective, anticonvulsant and antiproliferative effects (Seenaiah et al, 2014)
Summary
Research into medicinal chemistry based on benzothiazoles has become a fast developing and progressively more active topic. A large number of therapeutic agents based on benzothiazole systems have been synthesized and evaluated in terms of their pharmacological properties (Gill et al, 2015; Fathy et al, 1988). We are engaged in developing synthetic strategies for benzothaizole systems that show important biological activity as novel antimicrobial and antiviral agents (Azzam et al 2017a,b, 2020a,b,c, 2021; Elgemeie et al, 2000a,b; 2020). Search for the moiety benzo[d]thiazol-2-yl joined to C(CN) C gave 27 hits, but none in which any further atom at the double bond was sulfur. A search for the group C— C(CN) C(S—C), with the first carbon atom three-coordinate, both sulfur atoms two-coordinate and not involving cyclicity, gave only five hits. The refcodes, references and absolute cis torsion angles NC—C C—S were as follows: CIYDIY, Kumar et al (2008), 9.9; MTBCEY, Abrahamsson et al (1974), 15.4; VAPJAA, Azzam et al (2017c), 7.3; VELSIP, Peng et al (2006), 3.6; ZEDJEX, Osaka et al (1994), 10.5
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