Vascular and myocardial effecfs of mecinarone

Pourrias, B; Friedrich, Françoise

doi:10.1016/0014-2999(78)90095-x

Cited by 7 publications

(15 citation statements)

References 10 publications

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“…A cold solution of aryldiazonium salt (0.01 mol) was prepared by adding a solution of sodium nitrite (1.00 g into 10 ml H 2 O) to a cold solution of 4-nitroaniline hydrochloride (1.38 g, 0.01 mol of 4-nitroaniline in 5 ml concentrated HCl) with stirring. The resulting solution of the aryldiazonium salt was then added to a cold solution of 2a (2.75 g, 0.01 mol) or 2b (3.05 g, 0.01 mol) in ethanol (50 ml) containing sodium hydroxide (0.015 mol, in 5 ml H 2…”

Section: -(46-dimethoxy and 467-trimethoxybenzofuran-5-yl)-2-[(4-mentioning

confidence: 99%

See 1 more Smart Citation

Benzofuranyl‐pyran‐2‐ones, ‐pyridazines, and ‐pyridones from naturally occurring furochromones (visnagin and khellin)

Keshk

2004

Heteroatom Chemistry

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Section: -(46-dimethoxy and 467-trimethoxybenzofuran-5-yl)-2-[(4-mentioning

confidence: 99%

“…Benzofuran derivatives are known to have a wide variety of pharmacological activitives [1][2][3][4][5][6]. Recent development in the field of 2H-pyran-2-one derivatives has shown a high importance in the field of medicinal chemistry.…”

Section: Introductionmentioning

confidence: 99%

Benzofuranyl‐pyran‐2‐ones, ‐pyridazines, and ‐pyridones from naturally occurring furochromones (visnagin and khellin)

Keshk

2004

Heteroatom Chemistry

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“…Structure-activity studies undertaken in our laboratories can be summarized as follows (all screening being conducted on vascular and nonvascular smooth muscle in vitro): (a) Shortening the 2-substituent (to produce the methyl-and ethyl-MDls) 3 38,157) Ryanodine (60) Cetiedil (80) Mannitol (38) Suloctidil (19) Cicletanine (22) Mecinarone ( 127) Tabernanthine (42) CV-159 (166) Methylenedioxyindenes (MDIs) Trimethoxybenzoates Dantrolene (…”

Section: Chemistry and Structure-activity Relationshipsmentioning

confidence: 99%

Experimental Pharmacology of the Methylenedioxyindenes

Rahwan

1989

Cardiovascular Drug Reviews

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Calcium antagonists represent the most important addition to the therapeutic armamentarium for the treatment of cardiovascular diseases since the advent of the padrenergic receptor blocking drugs. Based on their cellular site of action, the calcium antagonists are broadly classified into two groups ( 13 1): the calcium channel blockers and the intracellular calcium antagonists. While the list of calcium channel blockers is expanding at a very rapid pace (Table I), that of intracellular calcium antagonists is relatively limited ( Table 2). Numerous recent reviews have been published on the calcium channel blockers (34,62,168), but only a few dealt with the intracellular calcium antagonists (62,13 l). While calcium channel blockers exert their pharmacological actions primarily by limiting calcium entry into cardiac or vascular smooth muscle cells, the intracellular calcium antagonists exert their actions by blocking intracelMar calcium receptors (e.g., troponin or calmodulin), preventing calcium mobilization from intracellular stores, facilitating calcium sequestration by intracellular organelles, enhancing calcium efflux from the cell, or interfering with the contractile proteins (1 3 1). The present review focuses on the methylenedioxyindenes (MDIs), a group of tertiary amine intracellular calcium antagonists developed in our laboratory (U.S. patents #4393226 and #4542153). The MDIs fulfill most of the criteria ( 13 I ) that qualify an agent to be classified primarily as an intracellular calcium antagonist. The MDIs inhibit the mobilization of calcium from the sarcoplasmic reticulum and preserve mitochondria1 structural and functional integrity against swelling and uncoupling of oxidative phosphorylation ( 132). DISCOVERY OF THE MDIsSerendipity and traditional pharmacological approaches contributed to the development of the MDIs. The MDIs were synthesized as intermediates (178) for the chemical synthesis of dibenzyloxyindanpropionic acids [DIPA (1 77)J (Fig. 1 ), in a research effort aimed at developing antiabortifacient prostaglandin FZa receptor antagonists, an endeavor that was ultimately successful (1 39). The intermediate MDIs

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“…Press,* Corris M. Hofmann, Nancy H. Eudy, Ivana P. Day, Eugene N. Greenblatt, and Sidney R. Safir Cardiovascular-CNS Disease Research Section, Medical Research Division of American Cyanamid Company, Lederle Laboratories, Pearl River, New York 10965. Received August 4,1980 10-(Alkylamino)thieno [3,4-b][l,5]benzoxazepines (3) and 10-(alkylamino)thieno [3,[4][5][6] [l,5]benzothiazepines (4) were prepared by derivatization of the respective lactams (7 and 8) via phosphorus pentachloride and subsequent condensation with the appropriate alky lamines. 9-(Alkylamino)-4fl-thieno [3,[4][5][6] [l,4]benzodiazepines (5) were prepared by titanium tetrachloride catalyzed condensation of the lactam 11 with alkylamines.…”

mentioning

confidence: 99%

“…Received August 4,1980 10-(Alkylamino)thieno [3,4-b][l,5]benzoxazepines (3) and 10-(alkylamino)thieno [3,[4][5][6] [l,5]benzothiazepines (4) were prepared by derivatization of the respective lactams (7 and 8) via phosphorus pentachloride and subsequent condensation with the appropriate alky lamines. 9-(Alkylamino)-4fl-thieno [3,[4][5][6] [l,4]benzodiazepines (5) were prepared by titanium tetrachloride catalyzed condensation of the lactam 11 with alkylamines. 9-(Alkylamino)-4-methylthieno [3,4-b] [ 1,4]benzodiazepines (6) were prepared by reductive alkylation of 5. The compounds were tested for potential neuroleptic activity by means of the blockade of d-amphetamine lethality in aggregated mice and/or effects on locomotor activity in rats.…”

mentioning

confidence: 99%

Thiophene systems. 5. Thieno[3,4-b][1,5]benzoxazepines, thieno[3,4-b][1,5]benzothiazepines, and thieno[3,4-b][1,4]benzodiazepines as potential central nervous system agents

Press¹,

Hofmann²,

Eudy³

et al. 1981

J. Med. Chem.

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10-(Alkylamino)thieno[3,4-b][1,5]benzoxazepines (3) and 10-(alkylamino)thieno[3,4-b][1,5]benzothiazepines (4) were prepared by derivatization of the respective lactams (7 and 8) via phosphorus pentachloride and subsequent condensation with the appropriate alkylamines. 9-(Alkylamino)-4H-thieno[3,4-b][1,4]benzodiazepines (5) were prepared by titanium tetrachloride catalyzed condensation of the lactam 11 with alkylamines. 9-(Alkylamino)-4-methylthieno[3,4-b][1,4]benzodiazepines (6) were prepared by reductive alkylation of 5. The compounds were tested for potential neuroleptic activity by means of the blockade of d-amphetamine lethality in aggregated mice and/or effects on locomotor activity in rats. Antidepressant activity was examined using inhibition of tetrabenazine-induced depression in mice. Most of the title compounds 3-6 were found to have neuroleptic activity. In addition, introduction of a 3-chloro substituent in the oxygen and sulfur systems (3p and 4c), as well as introduction of an N-alkyl in the dinitrogen system (6), was found to produce antidepressant effects. Structure-activity relationships are discussed.

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Vascular and myocardial effecfs of mecinarone

Cited by 7 publications

References 10 publications

Benzofuranyl‐pyran‐2‐ones, ‐pyridazines, and ‐pyridones from naturally occurring furochromones (visnagin and khellin)

Benzofuranyl‐pyran‐2‐ones, ‐pyridazines, and ‐pyridones from naturally occurring furochromones (visnagin and khellin)

Experimental Pharmacology of the Methylenedioxyindenes

Thiophene systems. 5. Thieno[3,4-b][1,5]benzoxazepines, thieno[3,4-b][1,5]benzothiazepines, and thieno[3,4-b][1,4]benzodiazepines as potential central nervous system agents

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