Pyrazolodiazepines. 2. 4-Aryl-1,3-dialkyl-6,8-dihydropyrazolo[3,4-e][1,4]diazepin-7(1H)-ones as antianxiety and anticonvulsant agents

Abstract

A series of 4-aryl-1,3-dialkyl-6,8-dihydropyrazolo[3,4-e] [1,4]diazepin-7(1H)-ones was synthesized and screened for psychotropic activity. In animals, a number of these pyrazolodiazepinones had strong CNS effects similar to diazepam. One compound, 4-(2-fluorophenyl)-6,8-dihydro-1,3,8-trimethylpyrazolo[3,4-e] [1,4]diazepin-7(1H)-one (54), is being studied in the clinic as a component of a new animal anesthetic, Tilazol.

Synthesis of 7-carboxyalkylthio-5,6,7,8-tetrahydro-1H-pyrazolo[3,4-e]diazepin-4-ones

“…В контексті зазна-ченого вище не втрачає своєї актуальності про-блема спрямованої модифікації інших гетероци-клічних систем тіоалканкарбоксильними заміс-никами. З урахуванням високого фармацевтично-го потенціалу піразоло [3,4-e] [1,4]діазепінів [9][10][11][12] предметом нашого розгляду стала їх екзофунк-ціоналізація фрагментами тіооцтової та тіопро-панової кислот.…”

Dipyrazolo[1,5-a:4',3'-c]pyridines – a new heterocyclic system accessed via multicomponent reaction

“…Condensed pyrazole scaffolds are important substructures of compounds with biological activity and can be found in some well-known drug molecules, such as, for example, Sildenafil (a pyrazolo[4,3- d ]pyrimidine) [1–2], Allopurinol (a pyrazolo[3,4- d ]pyrimidin-4-one) [3], Zaleplon (a pyrazolo[1,5- a ]pyrimidine) [4], and Zolazepam (a pyrazolo[3,4- e ][1,4]diazepine derivative, used in veterinary medicine) [5]. Particularly pyrazolopyrimidines are a very frequently accessed class of compounds [6] with the particular importance of the pyrazolo[3,4- d ]pyrimidine core, which can closely mimic the purine system of adenosine and, thus, has been incorporated in various compounds impairing protein kinases and ATPases [7–9].…”

Electrochemical Studies on Some Pyrazole, Oxadiazole, and Thiadiazole Derivatives

“…On the other hand, interest in the chemistry of pyrazoles and fused pyrazoles has been reviewed [1]. Several condensed pyrazoles have shown pharmacological activities as antipyretics [2], analgesics [3], CAMP phosphiasterase inhibitory action [4][5][6], and CNS activity [7,8]. Benzthiazoles and benzthiadiazole rings have always been the subject of permanent interest, due to their wide medical action.…”