- Friedel–Crafts reactions of acyl trifluoromethanesulfonates and cyclic acylsulfonium cations generated from acyl fluorides
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Reactive acyl trifluoromethanesulfonates are formed from the reaction of acyl fluorides with trimethylsilyl trifluoromethanesulfonate (TMSOTf). These electrophiles undergo Friedel–Crafts reactions with electron-rich aromatics at room temperature. When a sulfur atom is present at their γ position, their cyclization to acylsulfonium cations is observed and is followed by a rearrangement leading to benzothiepinones (or dibenzo[b,e]thiepinones) in 40–85% yield.
- Raghavendra Rao,Vallée, Yannick
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p. 4442 - 4447
(2016/07/06)
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- Analogues of N,1-diphenyl-4,5-dihydro-1H-[1]benzothiepino[5,4-c]pyrazole-3- carboxamide and N,1-diphenyl-4,5-dihydro-1H-[1]benzothiepino[5,4-c]pyrazole-3- carboxamide-6,6-dioxide: Syntheses, characterization, antimicrobial, antituberculosis, and antitumor activity
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A series of N,1-diphenyl-4,5-dihydro-1H-[1]benzothiepino[5,4-c]pyrazole-3- carboxamides (11a-m) and N,1-diphenyl-4,5-dihydro-1H-[1]benzothiepino[5,4-c] pyrazole-3-carboxamide-6,6-dioxides (12a-m) were synthesized by varying the active part (carboxamide group) of the pyrazole and were characterized by IR, 1H-NMR, 13C-NMR, mass spectral data, and elemental analyses. All compounds were evaluated for their antibacterial and antifungal activity. Compounds 11k and 12k showed higher activity than chloroamphenicol against Klebsiella pneumonia and Escherichia coli. Compounds 11b, 11c, 11l, 12b, 12c, and 12l displayed higher activity towards amikacin in inhibiting the growth of Escherichia coli (MIC 3.125 mg mL-1). Compounds 11k and 12k were equipotent to clotrimazole in inhibiting the growth of Candida albicans (MIC 3.125 mg mL-1). All compounds were screened for their cytotoxic activity against two tumor cell lines, namely the human colon tumor cell line (HCT116) and human cervical cancer cell line (HeLa). Most of the test compounds exhibited potent antitumor activity, especially compounds 11k and 12k, which displayed the highest activity among the test compounds with an IC50 equal to 18 and 12 μM for HeLa cells, and 16 and 10 μM for HCT116 cells, respectively. All the synthesized compounds showed low to moderate inhibitory activities against M. tuberculosis (MTB) H37Rv, whereas 11k and 12k were found to be more active against M. tuberculosis, with MIC values of 8.2 and 7.8 μM, compared to other analogues.
- Palanisamy, Pandaram,Kumaresan, Sudalaiandi
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p. 4704 - 4715
(2013/05/08)
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- Synthesis, characterization, antimicrobial, anticancer, and antituberculosis activity of some new pyrazole, isoxazole, pyrimidine and benzodiazepine derivatives containing thiochromeno and benzothiepino moieties
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In an attempt to find a new class of antimicrobial, anticancer, and antituberculosis agents, a series of pyrazole, isoxazole, pyrimidine and benzodiazepine derivatives containing thiochromeno and benzothiepino moieties were prepared via the reaction of diketoester 2 and 11 with appropriate chemical reagents. Single crystal XRD studies have been done on compounds 3 and 12. All compounds were evaluated for antimicrobial, anticancer, and antituberculosis activity. The benzodiazepine compounds (9 and 18) displayed the highest activity among the tested compounds with an IC50 equal to 15 and 16 μM for HeLa cells, and 13 and 12 μM for HCT116 cells. They were also found to be more active against H37Rv with an MIC of 7.0 and 6.5 μM compared to other analogues. Similarly these compounds (9 and 18) showed higher activity than chloroamphenicol against Klebsiella pneumoniae and Escherichia coli.
- Palanisamy, Pandaram,Jenniefer, Samson Jegan,Muthiah, Packianathan Thomas,Kumaresan, Sudalaiandi
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p. 19300 - 19310
(2013/10/22)
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- Discovery of Lu AA33810: A highly selective and potent NPY5 antagonist with in vivo efficacy in a model of mood disorder
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The structure-activity relationship of a series of tricyclic-sulfonamide compounds 11-32 culminating in the discovery of N-[trans-4-(4,5-dihydro-3,6- dithia-1-aza-benzo[e]azulen-2-ylamino)-cyclohexylmethyl]-methanesulfonamide (15, Lu AA33810) is reported. Compound 15 was identified as a selective and high affinity NPY5 antagonist with good oral bioavailability in mice (42%) and rats (92%). Dose dependent inhibition of feeding was observed after i.c.v. injection of the selective NPY5 agonist ([cPP1-7,NPY19-23,Ala 31,Aib32,Gln34]-hPP). In addition, ip administration of Lu AA33810 (10 mg/kg) produced antidepressant-like effects in a rat model of chronic mild stress.
- Packiarajan, Mathivanan,Marzabadi, Mohammad R.,Desai, Mahesh,Lu, Yalei,Noble, Stewart A.,Wong, Wai C.,Jubian, Vrej,Chandrasena, Gamini,Wolinsky, Toni D.,Zhong, Hualing,Walker, Mary W.,Wiborg, Ove.,Andersen, Kim
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scheme or table
p. 5436 - 5441
(2011/10/12)
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- Polycyclic thiazolidin-2-ylidene amines, process for their preparation, and their use as pharmaceuticals
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Polycyclic thiazolidin-2-ylidene amines and their physiologically tolerable salts and physiologically functional derivatives of the formula I in which the radicals have the meanings indicated, and their physiologically tolerable salts and a process for their preparation are described. The compounds are suitable, for example, as anorectics.
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