104386-39-2Relevant academic research and scientific papers
Isoquinolylquinoline Derivatives: Part III - Synthesis of Some 4-Substituted 3-(3',4'-Dihydro-1'-isoquinolyl)quinoline Derivatives as Possible Antifilarial Agents
Chakravorti, S. S.,Sen Gupta, Pranab K.,Chaudhuri, Subhankar,Das, Michael,Bhattacharya, Sipra,et al.
, p. 737 - 746 (2007/10/02)
Bischler-Napieralski cyclisation of the amides Va, Vb and Vc using PPA or PPA-POCl3 affords the corresponding 3,4-dihydroisoquinolylquinoline derivatives (VIa, VIb and VIc).Compounds VIc and IXa on treatment with POCl3 are converted into VIe and IXb which on subsequent reaction with sodium methoxide afford VIf and IXc respectively.With HBr (48percent), both VIc and VIe afford the hydrobromide of the corresponding 4,8-dihydroxyquinoline derivative (VIg).Compounds VIe and IXb further react with morpholine, piperidine, N-methylpiperazine, N-benzylpiperazine, N-carbethoxypiperazine, N-phenylpiperazine, etc., to give 4-substituted-amino derivatives VIIIa-e and IXd-g respectively.Compound VIc on dehydrogenation with Pd/C in tetralin is converted into VIIa; however under similar conditions VIe is converted into VIIb as a result of dehydrogenation and hydrogenolysis by hydrogen transfer.Four new compounds, X, XIa, XIb and XII having structural analogy with amodiaquine, have been prepared by the interaction of 4-acetamido-α-diethylamino-o-cresol with VIh, VIi, VIe and IXb respectively.Reaction of VIh with 1-diethylamino-4-aminopentane furnishes XIII.From preliminary pharmacological study it appears that compounds X and XII as hydrochlorides, posess significant antifilarial property.
