1,4-Dihydrobenzothieno[3,2-b]pyridine-5,5-dioxides

Dubure, R. R.; Vı̄gante, Brigita; Ozols, Ya. Ya.; Dubur, G. Ya.; Rozentale, G. I.

doi:10.1007/bf00471815

Chem Heterocycl Compd

1986

DOI: 10.1007/bf00471815

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1,4-Dihydrobenzothieno[3,2-b]pyridine-5,5-dioxides

R. R. Dubure

Brigita Vı̄gante

Ya. Ya. Ozols

et al.

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Cited by 3 publications

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“…We have previously shown that 5-oxo-4,5-dihydroindeno[1,2-b]pyridines [17] and 1,4-dihydrobenzothieno[3,2-b]pyridine 5,5-dioxides [18] which contain aryl substituents at position 4 have high coronary dilator and antioxidant activity [19][20][21]. 5-Oxo-4,5-dihydroindeno[1,2-b]pyridines with heterocyclic substituents [3-pyridyl-, 4-(3-phenylpyrazolyl)-] at position 4 shown marked antitumor activity [22].…”

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confidence: 99%

4-(10-Methyl-10H-phenothiazin-3-yl)-1,4-dihydropyridines, 4,5-dihydroindeno[1,2-b]-and 5,5-dioxo-4,5-dihydrobenzo-thieno[3,2-b]pyridines

Vı̄gante

Tirzītis

Tirzīte

et al. 2007

Chem Heterocycl Compd

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Keywords: 10-methyl-10H-phenothiazin-3-carbaldehyde, 1,4-dihydropyridine, Hantzsch synthesis, 4-(10-methyl-10H-phenothiazin-3-yl)-5-oxo- 1H-4,5-dihydroindeno[1,2-b]pyridine.Highly effective coronary dilators [1, 2] and hypotensive agents [3] have already been discovered amongst 4-aryl-and 4-hetaryl-1,4-dihydropyridines (1,4-DHP) but this has not diminished the synthesis of novel 1,4-DHP's with the aim of finding compounds having an altered profile of pharmacological properties. It is known that the 1,4-DHP structure can be regarded as a pharmacophoric group or "special structure" and the variation of the substituent in the DHP ring might be expected to give a selective action of the 1,4-DHP on various cell membrane receptors [4].The antioxidant activity of 1,4-DHP has been investigated [5, 6] and its correlation with pharmacological properties discussed [7,8]. It was found that the exchange of an o-nitrophenyl group at position 4 of the 1,4-DHP for a polycyclic heterocyclic substituents (xanthone, azaxanthen-9-one, thioxanthen-9-one) had a marked effect on inotropic and vasodilator activity [9, 10]. 1,4-DHP and 4,5-dihydro-indenopyridines containing lipophilic and bulky substituents show inhibitory activity on glutathione-S-transferase [11].At the same time, phenothiazine derivatives can possess high antioxidant, antiradical, neuroprotective, and antitumor activity [12,13]. In recent years phenothiazine derivatives have been investigated as neuroprotectors of nerve cells in Alzheimer [14] and Creutzfeld-Jakob deseases [15]. In combination this encouraged us to synthesize 1,4-DHP derivatives having the two pharmacotropic groups (1,4-DHP and phenothiazine) in the same molecule.To prepare the novel series of monocyclic 1,4-DHP 2, 5-oxo-4H-dihydroindeno[1,2-b]pyridines 5, and also 5,5-dioxo-4,5-dihydrobenzothieno[3,2-b]pyridines 8 we have employed different modifications of the Hantzsch synthesis using 10-methyl-10H-phenothiazine-3-carbaldehide 1 as the aldehyde component. Hence the 1,4-DHP 2b was prepared in 42% yield by refluxing the aldehyde 1 with acetoacetic ester and ammonia in ethanol (Scheme 1, method A). The corresponding dimethyl ester of the 1,4-DHP-3,4-dicarboxylic acid 2a was __________________________________________________________________________________________

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4-(10-Methyl-10H-phenothiazin-3-yl)-1,4-dihydropyridines, 4,5-dihydroindeno[1,2-b]-and 5,5-dioxo-4,5-dihydrobenzo-thieno[3,2-b]pyridines

Vı̄gante

Tirzītis

Tirzīte

et al. 2007

Chem Heterocycl Compd

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Benzo[b]thiophen-3(2H)-one 1,1-dioxide—a versatile reagent in the synthesis of spiroheterocycles

et al. 2008

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Unusual cyclization of 1-thianaphthenone-3-dioxide-1,1 to a 1,5-diazabicyclo[3.3.1]nonane—a heterocyclic analogue of a Tröger's base

Čekavičus

Лиепиньш

Vı̄gante

et al. 2001

Tetrahedron Letters

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1,4-Dihydrobenzothieno[3,2-b]pyridine-5,5-dioxides

Cited by 3 publications

References 5 publications

4-(10-Methyl-10H-phenothiazin-3-yl)-1,4-dihydropyridines, 4,5-dihydroindeno[1,2-b]-and 5,5-dioxo-4,5-dihydrobenzo-thieno[3,2-b]pyridines

4-(10-Methyl-10H-phenothiazin-3-yl)-1,4-dihydropyridines, 4,5-dihydroindeno[1,2-b]-and 5,5-dioxo-4,5-dihydrobenzo-thieno[3,2-b]pyridines

Benzo[b]thiophen-3(2H)-one 1,1-dioxide—a versatile reagent in the synthesis of spiroheterocycles

Unusual cyclization of 1-thianaphthenone-3-dioxide-1,1 to a 1,5-diazabicyclo[3.3.1]nonane—a heterocyclic analogue of a Tröger's base

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