Synthesis of 1, 5-Benzothiazepine Derivatives. III

Kugita, Hiroshi; Inoue, Hirozumi; Ikezaki, Muneyoshi; Konda, Mikihiko; Takeo, Satoshi

doi:10.1248/cpb.19.595

Cited by 73 publications

(15 citation statements)

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“…1) were tested using different procedures (Table 1) [3]. The homogeneity of the pharmacological data was verified by testing compound 1 [4] using the three different procedures (A, B and C) and it is possible to refer to it. Compound 1 (Diltiazem) has been studied considering the S,S enantiomer which shows Ca 2+ antagonist activity.…”

Section: Introductionmentioning

confidence: 99%

“…Compound 1 (Diltiazem) has been studied considering the S,S enantiomer which shows Ca 2+ antagonist activity. It is interesting to note that, like compounds 5 [4], 6 [5], 7 [5] and 8 [5], the diltiazem R,R enantiomer does not present the 'Ca 2+ channel blocker' effect, whereas compounds 2 [6], 3 [7] and 4 [7] show a significant Ca 2+ antagonist activity. …”

Section: Introductionmentioning

confidence: 99%

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Structure-activity relationship of Ca2+ channel blockers: A study using conformational analysis and chemometric methods

Belvisi¹,

Brossa²,

Salimbeni

et al. 1991

J Computer-Aided Mol Des

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A structure-activity relationship study has been done on 8 compounds with the activity known as 'Ca2+ channel blockers'. Conformational analysis was carried out using a molecular mechanics method. The 3D-QSAR approach was used and the most polar functional groups present in all the molecules were considered. Eight interatomic distances are necessary to define the relative spatial disposition of these relevant molecular fragments. The structure-activity relationship between interatomic distances and biological activity was performed using statistic and chemometric methods. In particular, with Principal Component Analysis, it was possible to reduce the number of interatomic distances: only six of the eight distances are sufficient to describe the system in a useful way. A classification method was iteratively used to select the most probable conformations linked to the biological activity and to build a model able to classify conformations according to their biological behaviour. Cluster analysis on the active selected conformations subsequently allowed the identification of two different geometrical patterns for the active compounds. Finally the validity of the model was verified by correctly predicting the activity of other molecules not used in the construction of the model but possessing known activity.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Structure-activity relationship of Ca2+ channel blockers: A study using conformational analysis and chemometric methods

Belvisi¹,

Brossa²,

Salimbeni

et al. 1991

J Computer-Aided Mol Des

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“…Diltiazem, cl-3-acetoxy-cis-2,3-dihydro-5-[2-(dimethylamino)ethyl]-2-(p-methoxyphenyl) 1,5-benzothiazepin-4(5H)-one hydrochloride (1), has been shown to be a potent coronary vasodilator (2). It produced a significant increase in coronary blood flow without in creasing myocardial oxygen consumption.…”

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confidence: 99%

Effect of Diltiazem on Electrical and Mechanical Activity of Isolated Cardiac Ventricular Muscle of Guinea Pig

Nakajima

Hoshiyama

Yamashita

et al. 1975

Japanese Journal of Pharmacology

174

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Abstract-Diltiazem, a new 1,5-benzothiazepine derivative, antagonized calcium ion and thus caused a reduction in the contractile force of isolated papillary muscle. The antagonistic ratio of diltiazem to calcium ion was estimated to be approx. 1 : 100. A lower concentration of diltiazem (2.2 yX 10-13 M) decreased the contractile force without affecting significantly the intracellularly recorded resting and action potentials. When the concentration of the compound was increased to 2.2 x 10-5 M, only the maximum rate of rise of the action potential was reduced, while the other parameters of the ac tion potential were also affected at 1

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“…2 Literature perusal of pharmacological studies of such moieties reveals that these compounds possess immense chemotherapeutic significance and are present as the core in a variety of drugs 3 ( Fig. 1), such as Prothioconazole-thiazocine, Diltiazem, Clotiapine, Omapatrilat, Promazine, Mesoridazine and Quetiapine, and exhibit a wide spectrum of pharmacological activities such as anticoagulant, 4 antiarterisoclerotic, 5 antihypertensive, 6 antidepressant, 7 antihistaminic, 8 anticonvulsant, 9 antidopaminergic, 10 tranquilizer, 11 antidepressant, 12 antihypertensive, 13 calcium channel blocker, 14 blood-platelet-aggregation inhibitors 15 and antiallergic agents. 16 A search for the applied methods for synthesis of medium-sized N,S-heterocyclic systems demonstrated that several established protocols are in practice, and comprehensive reviews of the syntheses and biological activities of various benzo-condensed 1,3-, 1,4-, 1,5-thiazepine and thiazocine regioisomers have been published.…”

Section: Introductionmentioning

confidence: 99%

Friedel-Crafts chemistry. Part 50. Convergent and diversity-oriented constructions of polycyclic quinolines via Friedel-Crafts and Beckmann ring enlargement approaches

El-Aal¹,

K.²

2017

Arkivoc

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Condensed heterocyclic systems containing N-& S-medium-sized rings, in particular, thiazepine, thiazocine, and thiazonine systems are important substructures present in a large variety of biologically active natural products. Methods for the formation of thiazonines and higher ring systems, however, remain largely unknown. The research presented addresses the synthesis and characterization of new heterocyclic skeletons incorporating N-& S-medium-sized-rings fused to quinolines to form the targeted tetracyclic 1,4-thiazocines, 1,4-thiazonines and 1,4-thiazecines by Friedel-Crafts cycliacylation and Beckmann-rearrangement sequences. The ambient conditions, short-reaction times and easy work-up procedures make this synthetic strategy a better protocol for the synthesis of medium-sized heterocyclic rings bearing nitrogen and sulphur atoms.

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Synthesis of 1, 5-Benzothiazepine Derivatives. III

Cited by 73 publications

References 0 publications

Structure-activity relationship of Ca2+ channel blockers: A study using conformational analysis and chemometric methods

Structure-activity relationship of Ca2+ channel blockers: A study using conformational analysis and chemometric methods

Effect of Diltiazem on Electrical and Mechanical Activity of Isolated Cardiac Ventricular Muscle of Guinea Pig

Friedel-Crafts chemistry. Part 50. Convergent and diversity-oriented constructions of polycyclic quinolines via Friedel-Crafts and Beckmann ring enlargement approaches

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