Basic derivatives of 6,7-dihydroindolo[1,7-ab][1]benzazepine and 6H-indolo[7,1-cd][1,5]benzoxazepine as potential antidepressant agents

Abstract

Basic derivatives of 6,7-dihydroindolo[1,7-ab][1]benzazepine and 6H-indolo[7,1-cd][1,5]benzoxazepine incorporating the imipramine basic side chain were synthesized and screened for antidepressant activity in mice. With few exceptions, the compounds unsubstituted at C-2 antagonized reserpine-induced ptosis and hypothermia showing negligible anticholinergic and antihistaminic properties. The compound 1-[2-(N-methyl-N-benzylamino)ethyl]-6,7-dihydroindolo[1,7-ab][1]benzazepine had the highest toxicity-activity ratio.

Novel latonduine derived proligands and their copper(ii) complexes show cytotoxicity in the nanomolar range in human colon adenocarcinoma cells andin vitrocancer selectivity

“…11-Bromo-7-hydrazin-yl-5,8-dihydroindolo [2,3- [2]benzazepin(6H)one (F) (76 mg, 0.22 mmol) in ethanol (2 mL) in a 10 mL Schlenk tube was degassed by bubbling argon through the solution for 10 min. 2-Acetylpyridine (27 µL, 0.24 mmol) was added and the mixture was stirred overnight at 85°C.…”

“…Indolobenzazepines are a class of compounds with a broad spectrum of biological activities, amongst them analgesic, antidepressant, antimalarial, antidiabetic, anticancer and antiparasitic. [1][2][3][4][5][6][7] The search for potent kinase inhibitors led to indolo [3,2-d]benzazepines, known as paullones. 8 Cyclin dependent kinases (cdks) are attractive targets for anticancer drugs, since they control the cell cycle.…”

Methods for the Synthesis of Isogramines and Their Chemical Properties. (Review)

“…Reduction of the readily obtainable dimethylamides of indole-2-carboxylic acids with lithium aluminum hydride also provides a convenient method for the synthesis of 2-dimethylaminomethylindoles [24][25][26][27][28][29][30][31]. Reduction of the formyl derivative 12, obtained in turn by successive transformation of indole-2-carboxylic acid into 2-acetylindole (13) with methyllithium, reductive amination to the amine 14, and formylation [32], was also used at one of the stages in the production of the 2-isogramine analog 2-(1-dimethylaminoethyl)indole (11).…”

Co(III)-Catalyzed Coupling-Cyclization of Aryl C–H Bonds with α-Diazoketones Involving Wolff Rearrangement

“…Meanwhile, N -phenyl group could also give 60% yield of 2-oxindole ( 3–1g ). Most importantly, several types of nitrogen-heterocycle substrates could still underwent smooth 2-oxindole formation to assemble fused tricyclic skeletons regardless of the ring size ( 3 - 1h – 3 - 1j , 54–67%), these complex cycles are commonly encountered in natural products and bioactive molecules . It should be noted that other substrates bearing oxidizing directing groups such as N ′-phenylacetohydrazide ( 1y ), N -(pivaloxy)­benzamide ( 1z ) and aceto O -povaloyl oxime ( 1z – a ) could not deliver the corresponding coupling-cyclization products, and these substrates could be almost completely recovered.…”