Synthesis, Characterization, X-Ray Crystal Structure, and Antimicrobial Activity of 1,1′-(3,4-Diphenylthieno[2,3-b]thiophene-2,5-diyl)diethanone

Yahia Nasser Mabkhot,Assem Barakat,Sammer Yousuf,S S Al-Showiman,M Iqbal Choudhary,Fahad D Aldawsari

doi:10.1155/2014/504860

Yahia Nasser Mabkhot, Assem Barakat + Show 4 more

Open Access

https://doi.org/10.1155/2014/504860

Copy DOI

Abstract

Synthesis of 1,1′-(3,4-diphenylthieno[2,3-b]thiophene-2,5-diyl)diethanone (4) is reported here. The structure of compound4was deduced by1H-NMR,13C-NMR, FT-IR, MS, microanalysis, and single-crystal X-ray diffraction. Compound crystallizes in the monoclinic space groupP21/nwitha= 9.3126(7) Å,b= 9.5867(7) Å,c= 20.2811(15) Å,α= 90°,β= 95.436(2)°,γ= 90°,V= 1802.5(2) Å3, andZ= 4. The molecules are packed in crystal structure by weak intermolecular C10–H10A⋯ S1 hydrogen bonding interactions. Compound4can be a useful intermediate for the synthesis of diphenylthieno[2,3-b]thiophene. Compound4was found to be active against Gram-positive bacteria (Bacillus subtilisandStaphylococcus pneumoniae) and Gram-negative bacteria (Escherichia coli) and also was found to be active against fungi (Aspergillus fumigatusandCandida albicans).

Highlights

Thienothiophenes skeletons are important in pharmaceutical research because of their versatile biological activities, such as antitumor, antiviral antibacterial, anticancer, antioxidant and β-glucuronidase and α-glucosidase inhibition, antiglaucoma activity, and inhibitors of platelet aggregation properties [1,2,3,4,5]
We have the synthesis of certain bis-heterocycles containing thieno[2,3b]thiophene derivatives
Antibacterial activities were investigated by using agar well diffusion method, against the Staphylococcus pneumonia (RCMB 010010) and Bacillus subtilis (RCMB 010067) {as Gram-positive bacteria} and Pseudomonas aeruginosa (RCMB 010043) and Escherichia coli (RCMB 0100052) {as Gram-negative bacteria}

Summary

Introduction

Thienothiophenes skeletons are important in pharmaceutical research because of their versatile biological activities, such as antitumor, antiviral antibacterial, anticancer, antioxidant and β-glucuronidase and α-glucosidase inhibition, antiglaucoma activity, and inhibitors of platelet aggregation properties [1,2,3,4,5]. Because of this thieno[2,3-b]thiophenes have been the focus of active research in recent years. Compound 4 was screened for in vitro antimicrobial activity

Experimental

CH3COCH2Cl

Results and Discussion

Conclusion