- Studies in Potential Filaricides: Part XIII - Synthesis of 1,4-Diazabicyclononanes, 1,4-Diazabicyclodecanes and 1,4-Diazabicycloundecanes as diethylcarbamazine Analogs
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1,4-Diazabicyclononanes (13 - 20), 1,4-diazabicyclodecanes (21 - 28), 1,4-diazabicycloundecanes (29 - 34), 1,4-diazabicyclononan-5-ones (37 - 41) and 1,4-diazabicyclodecan-5-ones (42 - 44) having alkyl and acyl substituents at 4-position have been synthesized and evaluated for their filaricidal activity against Litomasoides carinii infection in cotton rats.Except 4-diethylcarbamoyl-1,4-diazabicyclononane (13), which exhibits significant activity, being about 3/5th as active as the standard diethylcarbamazine (DEC), none of the other compounds shows any activity against adult worms.The results have been rationalised in terms of critical bulk around the N-1 of the piperazine ring of DEC.From this work and earlier published results it appears that both axial and equatorial N-CH3 bonds in DEC are acceptable for activity.
- Shukla, U. K.,Khanna, J. M.,Sharma, Satyavan,Anand, Nitya,Chatterjee, R. K.,Sen, A. B.
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p. 664 - 668
(2007/10/02)
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