Syntheses of new tetrasubstituted thiophenes as novel anti-inflammatory agents

Synthesis and vibrational spectral (FT-IR, FT-Raman) studies, NLO properties & NBO analysis of (E)-N'(thiophen-2yl methylene)isonicotinohydrazide using quantum chemical method

“…Some orbitals are electron donor and some are acceptors, the energy difference between such bonding and antibonding orbitals makes the molecule susceptible for interactions (Liu et al., 2005; James et al, 2006). The larger energy difference E (2) value, the more intensive is the interaction i.e. more is donating tendency of electron from one orbital and more is the accepting tendency of other orbital, which makes the interaction between them stronger.…”

“…The various acceptors for different donor clearly indicate that the intra-molecular interaction are found by the orbital overlap between different bonding and respective anti-bonding orbitals, which results intra-molecular charge transfer (ICT) causing stabilization of the system . These interactions increase with increase in electron density (ED) difference and the stabilization energy E (2) between the donor and acceptor levels of C-C, C-H bonding and anti-bonding orbitals. The E (2) energy values and types of the transition are shown in Table 6.…”

“…Especially, thiophene derivatives have been reported to possess broad spectrum of biological properties including anti-inflammatory, analgesic, anti-depressant, anti-microbial and anti-convulsant activities (Molvi et al, 2007;SatheeshaRai et al, 2008;Ashalatha et al, 2007). Now, presently available active anti-epileptic drugs like tiagabine, etizolam, brotizolam are containing thiophene moiety in their structures as active pharmacophore (Polivka et al, 1984;Noguchi et al, 2004).…”

Four closely related N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)benzamides: order versus disorder, and similar molecular conformations but different modes of supramolecular aggregation, with a new disordered refinement of 2-amino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophene

“…Thiophene derivatives exhibit a wide range of biological properties, including analgesic activity (Cannito et al, 1990;Molvi et al, 2007), anti-inflammatory activity (Cannito et al, 1990;Ashalatha et al, 2007;Molvi et al, 2007), antimicrobial activity (Ashalatha et al, 2007;Rai et al, 2008) and NOscavenging activity (Molvi et al, 2007); in addition, 2-amino-3-benzoylthiophenes can act as allosteric enhancers at the A 1 adenosine receptor (Aurelio et al, 2010). With this in mind, we synthesized and characterized a series of four variously sub- N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-benzamides (Scheme 1), whose structures we report here, namely N- (3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-3-fluorobenzamide, (I), N-(3-benzoyl-4,5,6,7-tetrahydrobenzo-[b]thiophen-2-yl)-4-chlorobenzamide, (II), N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-2,6-difluorobenzamide, (III),5,6,thiophen-2-yl)-2-methoxybenzamide, (IV), and we compare the structures of (I)-(IV) with those of the recently reported analogue N- (3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)benzamide, (V) (Scheme 2) , and the parent amine 2-amino-3-benzoyl-4, 5,6,7-tetrahydrobenzo[b]thiophene, (VI) (Kubicki et al, 2012).…”

Synthesis, cytotoxic and anti-proliferative activity of novel thiophene, thieno[2,3-b]pyridine and pyran derivatives derived from 4,5,6,7-tetrahydrobenzo[b]thiophene derivative

“…Nowadays benzothiophene derivatives in combination with other ring systems have been used extensively in pharmaceutical applications. [1][2][3] A large number of compounds containing thiophene system have been investigated because of their broad spectrum of biological activities which include analgesic, 4 antibacterial, 5 antifungal, 6 antiparasitic, 7 antiviral, 8 anti-inflammatory, 9 anticonvulsant, 10 anti-nociceptive, 11 DNA cleavage, 12 herbicidal, 13 antitubercular, 14 protein kinase inhibition, 15 respiratory syndrome protease inactivation, 16 an active ester in the peptide synthesis and agonists of peroxisome proliferator activated receptors. 17 In addition to these considerable biological applications, tetrahydrobenzo [b]thiophenes are important intermediates, protecting groups and final products in organic synthesis.…”