Synthesis, X-ray analysis and computational studies of two novel thiophene derivatives

References

• Shah R, Verma PK. Therapeutic importance of synthetic thiophene. Chem Cent J. 2018;12(1):137. doi: 10.1186/s13065-018-0511-5
   PubMedGoogle Scholar
• Mabkhot YN, Kaal NA, Alterary A, et al. New thiophene derivatives as antimicrobial agents. J. Heterocyclic Chem. 2019;56(10):2845–2953. doi: 10.1002/jhet.3688
   Web of Science ®Google Scholar
• Pathania S, Narang RK, Rawal RK. Role of sulphur-heterocycles in medicinal chemistry: An update. Eur J Med Chem. 2019;180:486–508. doi: 10.1016/j.ejmech.2019.07.043
   PubMed Web of Science ®Google Scholar
• Khalil AM, Berghot MA, Gouda MA. Synthesis and antibacterial activity of some new thiazole and thiophene derivatives. Eur J Med Chem. 2009;44:4434–4440. doi: 10.1016/j.ejmech.2009.06.002
   PubMed Web of Science ®Google Scholar
• Sharma S, Athar F, Maurya MR, et al. Copper (II) complexes with substituted thiosemicarbazones of thiophene-2-carboxaldehyde: synthesis, characterization and antiamoebic activity against E. histolytica. Eur J Med Chem. 2005;40(12):1414–1419. doi: 10.1016/j.ejmech.2005.05.013
   PubMed Web of Science ®Google Scholar
• Alagarsamy V, Raja Solomon V, Meenac R, et al. Design and synthesis of 2-Methylthio-3-substituted-5, 6-dimethylthieno [2,3-d] pyrimidin-4(3H)-ones as analgesic, anti-inflammatory and Antibacterial Agents. Med Chem. 2007;3(1):67–73. doi: 10.2174/157340607779317599
   PubMed Web of Science ®Google Scholar
• Deka S, Mohan S, Saravanan J, et al. Syntheses, characterization and in-vitro anti-inflammatory activity of some novel thiophenes. Maced J Med Sci. 2012;5:159–163.
   Google Scholar
• Forsch RA, Wright JE, Rosowsky A. Synthesis and in vitro antitumor activity of thiophene analogues of 5-chloro-5,8-dideazafolic acid and 2-methyl-2-desamino-5-chloro-5,8-dideazafolic acid. Bioorg Med Chem. 2002;10:2067–2076. doi: 10.1016/S0968-0896(02)00018-4
   PubMed Web of Science ®Google Scholar
• Saad HA, Youssef MM, Mosselhi MA. Microwave assisted synthesis of some new fused 1,2,4-triazines bearing thiophene moieties with expected pharmacological activity. Molecules. 2011;16:4937–4957. doi: 10.3390/molecules16064937
   PubMed Web of Science ®Google Scholar
• Rashad AE, Shamroukh AH, Abdel-Megeid RE, et al. Synthesis and screening of some novel fused thiophene and thienopyrimidine derivatives for anti-avian influenza virus (H5N1) activity. Eur J Med Chem. 2010;45:5251–5257. doi: 10.1016/j.ejmech.2010.08.044
   PubMed Web of Science ®Google Scholar
• Sharma C, Yerande S, Chavan R, et al. Synthesis of thienopyrimidines and their antipsychotic activity. J Chem. 2010;7(2):655–664.
   Web of Science ®Google Scholar
• Abdelhamid AO. Convenient synthesis of some new Pyrazolo (1, 5-a pyrimidine, Pyridine, thieno[2,3-b]pyridine, and isoxazolo[3,4-d]pyridazine derivatives containing Benzofuran Moiety. J Heterocycl Chem. 2009;46(4):680–686. doi: 10.1002/jhet.141
   Web of Science ®Google Scholar
• Laddha SS, Bhatnagar SP. A new therapeutic approach in Parkinson’s disease: Some novel quinazoline derivatives as dual selective phosphodiesterase 1 inhibitors and anti-inflammatory agents. Bioorg Med Chem. 2009;17(19):6796–6802. doi: 10.1016/j.bmc.2009.08.041
   PubMed Web of Science ®Google Scholar
• Wardakhan W, Abdel-Salam O, Elmegeed G. Screening for antidepressant, sedative and analgesic activities of novel fused thiophene derivatives. Acta Pharm. 2008;58(1):1–14. doi: 10.2478/v10007-007-0041-5
   PubMed Web of Science ®Google Scholar
• Shireesha B, UmaShankar K, RaghuramRao A, et al. Design, synthesis and H1-antihistaminic activity of novel [2,3-d] pyrimidinones. Int J Pharm Sci Nanotechnol. 2008;1(2):136–143.
   Google Scholar
• Connor DT, Sorenson RJ, Cetenko WA, et al. Synthesis and antiallergy activity of 10-oxo-10H-pyrido [1,2-a] thieno [3,2-d] pyrimidines and 10-oxo-10H-pyrido [1,2-a] thieno [3,4-d] pyrimidines. J Med Chem. 1984;27(4):528–530. doi: 10.1021/jm00370a016
   PubMed Web of Science ®Google Scholar
• Shah R, Verma PK. Synthesis of thiophene derivatives and their anti-microbial, antioxidant, anticorrosion and anticancer activity. BMC Chemistry. 2019;13(1):54. doi: 10.1186/s13065-019-0569-8
   PubMedGoogle Scholar
• Pinto E, Queiroz MRP, Vale-Silva LA, et al. Antifungal activity of synthetic di (hetero) arylamines based on the benzo[b]thiophene moiety. Bioorg Med Chem. 2008;16(17):8172–8177. doi: 10.1016/j.bmc.2008.07.042
   PubMed Web of Science ®Google Scholar
• Russell RK, Press JB, Rampulla RA, et al. Thiophene systems: thienopyrimidinedione derivatives as potential antihypertensive agents. J Med Chem. 1988;31:1786–1793. doi: 10.1021/jm00117a019
   PubMed Web of Science ®Google Scholar
• Yen MS, Wang IJ. Synthesis and absorption spectra of hetarylazo dyes derived from coupler 4-aryl-3-cyano-2-aminothiophenes. Dyes Pigments. 2004;61(3):243–250. doi: 10.1016/j.dyepig.2003.10.015
   Web of Science ®Google Scholar
• Rost C, Karg S, Riess W, et al. Ambipolar light-emitting organic field-effect transistor. Appl Phys Lett. 2004;85:1613–1615. doi: 10.1063/1.1785290
   Web of Science ®Google Scholar
• Yu HH, Pullen AE, Büschel MG, et al. Charge-specific interactions in segmented conducting polymers: an approach to selective ionoresistive responses. Angew Chem Int Ed Engl. 2004;43(28):3700–3703. doi: 10.1002/anie.200453896
   PubMed Web of Science ®Google Scholar
• Benabdellah M, Aouniti A, Dafali A, et al. Investigation of the inhibitive effect of triphenyltin- 2-thiophene carboxylate on corrosion of steel in 2M H3PO4 solutions. Appl Surf Sci. 2006;252:8341–8347. doi: 10.1016/j.apsusc.2005.11.037
   Web of Science ®Google Scholar
• Kim C, Choi KS, Oh JH, et al. The effects of octylthiophene ratio on the performance of thiophene based polymer light-emitting diodes. Sci Adv Mater. 2015;7:2401–2409. doi: 10.1166/sam.2015.2669
   Web of Science ®Google Scholar
• Mabkhot YN, Al-Showiman SS, Soliman SM, et al. Synthesis, characterization, X-ray structure, computational studies, and bioassay of novel compounds combining thiophene and benzimidazole or 1,2,4-triazole moieties. Chem Cent J. 2017;11(1):51. doi: 10.1186/s13065-017-0280-6
   PubMedGoogle Scholar
• Mabkhot YN, Alatibi F, El-Sayed NN, et al. Synthesis and structure-Activity Relationship of Some New thiophene-Based Heterocycles as potential antimicrobial Agents. Molecules. 2016;21(8):1036. doi: 10.3390/molecules21081036
   Web of Science ®Google Scholar
• Mabkhot YN, Aldawsari FD, Al-Showiman SS, et al. Novel enaminone derived from thieno[2,3-b]thiene: synthesis, x-ray crystal structure, HOMO, LUMO, NBO analyses and biological activity. Chem Cent J. 2015;9(24). doi:10.1186/s13065-015-0100-9.
   Google Scholar
• Mabkhot YN, Alatibi F, El-Sayed NN, et al. Antimicrobial Activity of Some novel Armed thiophene derivatives and Petra/osiris/molinspiration (POM) analyses. Molecules. 2016;21(2):222. doi: 10.3390/molecules21020222
   PubMed Web of Science ®Google Scholar
• Mabkhot YN, Kheder NA, Barakat A, et al. Synthesis, antimicrobial, anti-cancer and molecular docking of two novel hitherto unreported thiophenes. RSC Adv. 2016;6:63724–63729. doi: 10.1039/C6RA09883E
   Web of Science ®Google Scholar
• Sheldrick GM. A short history of SHELX. Acta Crystallogr. 2008;A64:112–122. doi: 10.1107/S0108767307043930
   Google Scholar
• Sheldrick GM. SHELXTL-PC (Version 5.1) Siemens Analytical Instruments. Madison (WI): Inc; 1997.
   Google Scholar
• Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian 03, Revision C.02, vol 24. Wallingford: Gaussian Inc; 2004.
   Google Scholar
• Dennington RD II, Keith TA, Millam J. Gauss View, Version 4.1. Shawnee Mission (KS): Semichem Inc; 2007.
   Google Scholar
• Zhurko GA, Zhurko DA. Chemcraft. Lite Version Build 08; 2005. Available online http://www.chemcraftprog.com/.
   Google Scholar
• Glendening ED, Reed AE, Carpenter JE, et al. Version 3.1, CI. Madison: University of Wisconsin; 1998.
   Google Scholar
• McKinnon JJ, Spackman MA, Mitchell AS. Novel tools for visualizing and exploring intermolecular interactions in molecular crystals. Acta Crystallogr B. 2004;60(6):627–668. doi: 10.1107/S0108768104020300
   PubMedGoogle Scholar
• Wolff SK, Grimwood DJ, McKinnon JJ, et al. Crystal Explorer 3.1 (2013). Crawley: University of Western Australia; 2005–2013; http://hirshfeldsurface.net/CrystalExplorer.
   Google Scholar
• Spackman MA, Jayatilaka D. Hirshfeld surface analysis. Cryst Eng Comm. 2009;11:19–32. doi: 10.1039/B818330A
   Web of Science ®Google Scholar
• McKinnon JJ, Jayatilaka D, Spackman MA. Towards quantitative analysis of intermolecular interactions with Hirshfeld surfaces. Chem Commun (Camb. 2007;37:3814–3816. doi: 10.1039/b704980c
   PubMed Web of Science ®Google Scholar
• Sheldrick GM. Crystal structure refinement with SHELXL. Acta Crystallogr C Struct Chem. 2015;71:3–8. doi: 10.1107/S2053229614024218
   PubMed Web of Science ®Google Scholar
• Jensen KA, Henriksen L. Studies of thioacids and their derivatives. XIV reactions of carbon disulfide with active methylene compounds. Acta Chem Scand. 1986;22:1107–1128. doi: 10.3891/acta.chem.scand.22-1107
   Google Scholar
• Hergue N, Frere P. Synthesis of 3,4-alkoxythieno[2,3-b]thiophene derivatives. The first block copolymer associating the 3,4-ethylenedioxythieno[2,3-b]thiophene (EDOThT) unit with 3,4-ethylenedioxythiophene (EDOT) moieties. Org Biomol Chem. 2007;5:3442–3449. doi: 10.1039/b712052d
   PubMed Web of Science ®Google Scholar
• Farhat MF, El-Saghier AMM, Makhlouf MA, et al. Ketene N,S-acetals in heterocyclic synthesis:part 1: synthesis of N-phenyl-2-ylidene and 2,5-diylidene-4-thiazolidinone derivatives. J Sulphur Chem. 2007;28:563–572. doi: 10.1080/17415990701586823
   Google Scholar
• Abu-Shanab F, Sherif S, Mousa S. Dimethylformamide dimethyl acetal as a building block in heterocyclic synthesis. J Heterocycl Chem. 2009;46:801–827. doi: 10.1002/jhet.69
   Web of Science ®Google Scholar
• Allen FH, Kennard O, Watson DG, et al. Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. bond lengths in organic compounds. J Chem Soc, Perkin Trans. 1987;2:S1–S19. doi: 10.1039/p298700000s1
   Google Scholar
• Politzer P, Murray JS. Relationships of electrostatic potentials to intrinsic molecular properties. vol 3. Amsterdam: Elsevier; 1996.
   Google Scholar
• Scrocco E, Tomasi J. Electronic molecular structure, reactivity and intermolecular forces: an euristic interpretation by means of electrostatic molecular potentials. Adv Quantum Chem. 1979;11:115–193. doi: 10.1016/S0065-3276(08)60236-1
   Google Scholar
• Fukui K, Yonezawa T, Shingu HJ. A moleculareorbital theory of reactivity in aromatic hydrocarbons. J Chem Phys. 1952;20:722–725. doi: 10.1063/1.1700523
   Web of Science ®Google Scholar
• Padmaja L, Ravikumar C, Sajan D, et al. Density functional study on the structural conformations and intramolecular charge transfer from the vibrational spectra of the anticancer drug combretastatin-A2. J Raman Spectrosc. 2009;40:419–428. doi: 10.1002/jrs.2145
   Web of Science ®Google Scholar
• Mabkhot YN, Barakat A, Soliman SM, et al. Synthesis, characterization and computational studies of a novel thieno[2,3-b] thiophene derivative. J Mol Struct. 2017;1130:62–70. doi: 10.1016/j.molstruc.2016.10.001
   Web of Science ®Google Scholar