6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines which have central nervous system depressant activity

Abstract

A series of 6-phenyI- 4H-s-ti'iazolo [4,3-] [ 1,4]benzodiazepines has been prepared by the reaction of 1,3-dihydro-5-phenyl-2fí-l,4-benzodiazepine-2-thiones with carboxylic acid hydrazides. Pharmacologic testing has demonstrated that this series has high CNS depressant activity with low concomitant toxicity.

Design of potent, orally effective, nonpeptidal antagonists of the peptide hormone cholecystokinin.

“…The data in Table 2 illustrate how substitution in the benzodiazepine ring affects CCK receptor binding potencies as compared with its influence on reported anti-anxiety activities. Thus, some substitutions such as 2'-fluoro (Y = F), N1-methyl (R1 = CH3), and N1-C2-triazole fusion [ZR1 = =N-N=C(CH3)-] have effects on CCK receptor affinity similar to those reported in the anti-anxiety series (33,39): they provide potent compounds in each case. N1-carboxymethyl (R, = CH2COOH), on the other hand, greatly reduces anti-anxiety potency (34), but gives potent CCK receptor ligands (13 and 20).…”

Design and Synthesis of New Bioactive 1,2,4-Triazoles, Potential Antitubercular and Antimicrobial Agents

“…The 1,2,4-triazole, as well found to exhibit antiasthmatic [14] , antiviral (ribavirin) [15] , antifungal (fluconazole) [16] , antimicrobial [17,18] , antibacterial [19][20][21] , insecticidal [22] , hypnotic [23] , cytotoxic [24] , antitubercular [25] and hypotensive [26,27] activities. This moiety was also found in potent agonist and antagonist receptor ligands [28,29] in HIV-1 protease inhibitors [30] and in thrombin inhibitors [31] .…”

Mass spectrometric studies of tetrasubstituted 3a,4,5,11-tetrahydro-3H-1,2,4-triazolo[4,3-d][1,5]benzothiazepines

“…[1][2][3][4] Their tricyclic derivatives with a fused five-membered 1,2,4-triazole ring show effective activities as potential central nervous system depressants, antipsychotic agents, anti-inflaminatory and antiallergic agents, etc. [5][6][7] Hence, much attention has been paid to their synthesis. [7][8][9] Here our aim was to study fragmentation mechanisms under electron impact (EI) of seven new tetrasubstituted 3a,4,5,11-tetrahydro-3H-1,2,4-triazolo [4,3-d] [1,5]benzothiazepines which had previously been synthesized and characterized by MS, 1 H NMR, IR and elemental analysis, for studies on the relationship of structure and activity.…”

“…[5][6][7] Hence, much attention has been paid to their synthesis. [7][8][9] Here our aim was to study fragmentation mechanisms under electron impact (EI) of seven new tetrasubstituted 3a,4,5,11-tetrahydro-3H-1,2,4-triazolo [4,3-d] [1,5]benzothiazepines which had previously been synthesized and characterized by MS, 1 H NMR, IR and elemental analysis, for studies on the relationship of structure and activity. 8,10 Their structures are shown as follows:…”