Benzo[1,5]thiazepine: Synthesis, Reactions, Spectroscopy, and Applications

El‐Bayouki, Khairy A. M.

doi:10.1155/2013/210474

Cited by 28 publications

(12 citation statements)

References 71 publications

(123 reference statements)

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“…Similarly, the presence of allyloxy group at the para position of the phenyl ring as displayed in case of compound 4r also enhanced the antibacterial activity. A decrease in the antifungal activity is attributed to the presence of nitro group on the phenyl ring at ortho or meta or para positions as displayed in the case of compounds 4j and 4k [23,24].…”

Section: Antimicrobial Activitymentioning

confidence: 95%

Microwave assisted synthesis and biological evaluation of a series of 1,5-benzothiazepines as potential cytotoxic and antimicrobial agents

et al. 2014

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Section: Antimicrobial Activitymentioning

confidence: 95%

Microwave assisted synthesis and biological evaluation of a series of 1,5-benzothiazepines as potential cytotoxic and antimicrobial agents

et al. 2014

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“…The general view of the molecule 4a is shown in Figure 1 and the main geometrical parameters are given in Table 1. Data from X-ray analysis proved the structure of 4a as indano[2,3b]-2-ferrocenylmethyl [1,4]benzothiazines. Table 1.…”

Section: Chemistrymentioning

confidence: 91%

“…The various reported methodologies involve the use of inorganic supports such as alumina, silica gel, AcOH, trifluoroacetic acid, HCl, piperidine, BF 3 Et 2 O, etc. to improve the reaction efficiency [2] [3] [4]. Likewise, the related 1,5-benzothiazepines display a comparable spectrum of biological activity.…”

Section: Introductionmentioning

confidence: 99%

“…Likewise, the related 1,5-benzothiazepines display a comparable spectrum of biological activity. The 1,5-benzothiazepine framework has been identified as a pluripotent pharmacophore with derivatives encompassing CNSacting agents [5], anti-HIV [6], anti-tuberculosis (TB) [7], anticancer drugs [8], antimicrobial [9], calmodulin antagonists [4], enzyme inhibitors [11], antifungal [4] [10], antibacterial [12], anti-inflammatory and analgesic agents [4]. Also, it is expected that new active benzo-1,5-thiazepines and other related derivatives could be used in the treatment of serious human diseases like Alzheimer's diabetes [4].…”

Section: Introductionmentioning

confidence: 99%

“…

AbstractA novel 2-indano[2,3b]-2-ferrocenyl-and 2-indano[2,3b]-2-(p-methoxyphenyl) [1,5]benzo-2,5-dihydrothiazepine 5a,b (addition Michael/cyclization) (~30.32%), indano[2,3b]-2-ferrocenyl-and 2-(p-methoxyphenyl) [1,4] benzothiazine 4a,b (addition "anti-Michael"/cyclization) (~45.43%), respectively, were obtained by the condensation of 2-ferrocenyl-and 2-(p-methoxyphenyl)methyliden-1,3-indandiones 1a,b with o-aminothiophenol 2 in the presence of AcOH and HCl. A new "anti-Michael" addition reaction of 1,4-bis-heteronucleophile 2 into 2-arylmethyliden-1,3-indandiones was reported.

As a result of this reaction the product 1a,b was obtained.

…”

mentioning

confidence: 99%

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“Anti-Michael” and Michael Additions in the Reactions of 2-Arylmethyliden-1,3-Indandiones with 2-Aminothiophenol

García¹,

Hernández-Suzan²,

Martínez-Klimova³

et al. 2017

IJOC

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A novel 2-indano[2,3b]-2-ferrocenyl-and 2-indano[2,3b]-2-(p-methoxyphenyl) [1,5]benzo-2,5-dihydrothiazepine 5a,b (addition Michael/cyclization) (~30.32%), indano[2,3b]-2-ferrocenyl-and 2-(p-methoxyphenyl) [1,4] benzothiazine 4a,b (addition "anti-Michael"/cyclization) (~45.43%), respectively, were obtained by the condensation of 2-ferrocenyl-and 2-(p-methoxyphenyl)methyliden-1,3-indandiones 1a,b with o-aminothiophenol 2 in the presence of AcOH and HCl. A new "anti-Michael" addition reaction of 1,4-bis-heteronucleophile 2 into 2-arylmethyliden-1,3-indandiones was reported.As a result of this reaction the product 1a,b was obtained. The structures of the resultant compounds were elucidated by IR, 1 H and 13 C NMR spectroscopy, mass spectrometry, elemental and X-ray diffraction analysis. The in vitro antitumor activity of the obtained products was researched using the following human cancer cell lines: glioblastoma (CNS U-251), prostatic adenocarcinoma (PC-3), chronic myelogenous leukemia (K562), colorectal adenocarcinoma (HCT-15), mammary adenocarcinoma (MCF-7), and small cell lung cancer (SKLU) and the sulforhodamine B (SRB) method. Among these new compounds some thiazine and thiazepine derivatives showed compelling in vitro antitumor effects on cell lines K-562, HCT-15, SKLU-1 and MCF-7.

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Synthesis of Potent and Selective HDAC6 Inhibitors Bearing a Cyclohexane‐ or Cycloheptane‐Annulated 1,5‐Benzothiazepine Scaffold

Vreese

Galle

Depetter

et al. 2016

Chemistry A European J

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Selective inhibitors of histone deacetylase 6 (HDAC6) are an emerging class of pharmaceuticals due to the involvement of HDAC6 in different pathways related to neurodegenerative diseases, cancer, and immunology. Herein, the synthesis of ten new benzohydroxamic acids, constructed by employing the tetrahydrobenzothiazepine core as a privileged pharmacophoric unit, is described. This is the first report on the synthesis and isolation of octahydrodibenzothiazepines and octahydro-6H-benzocycloheptathiazepines, which were then used to develop a new class of HDAC6 inhibitors. Evaluations of their HDAC-inhibiting activity resulted in the identification of cis-N-(4-hydroxycarbamoylbenzyl)-1,2,3,4,4a,5,11,11a-octahydrodibenzo[b,e][1,4]thiazepine-10,10-dioxide and cis-N-(4-hydroxycarbamoylbenzyl)-7-trifluoromethyl-1,2,3,4,4a,5,11,11a-octahydrodibenzo[b,e][1,4]thiazepine-10,10-dioxide as highly potent and selective HDAC6 inhibitors with activity in the low nanomolar range, which also show excellent selectivity on the enzymatic and cellular levels. Furthermore, four promising inhibitors were subjected to an Ames fluctuation assay, which revealed no mutagenic effects associated with these structures.

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Benzo[1,5]thiazepine: Synthesis, Reactions, Spectroscopy, and Applications

Cited by 28 publications

References 71 publications

Microwave assisted synthesis and biological evaluation of a series of 1,5-benzothiazepines as potential cytotoxic and antimicrobial agents

Microwave assisted synthesis and biological evaluation of a series of 1,5-benzothiazepines as potential cytotoxic and antimicrobial agents

“Anti-Michael” and Michael Additions in the Reactions of 2-Arylmethyliden-1,3-Indandiones with 2-Aminothiophenol

Synthesis of Potent and Selective HDAC6 Inhibitors Bearing a Cyclohexane‐ or Cycloheptane‐Annulated 1,5‐Benzothiazepine Scaffold

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