naa a22 4500 510733379 CHVBK 20180411083001.0 cr unu---uuuuu 180411e20130101xx s 000 0 eng 10.1007/s12039-012-0346-x doi (NATIONALLICENCE)springer-10.1007/s12039-012-0346-x Comparison of anti amoebic activity of stereoisomeric diamino and monoamino pregnene alkaloids and their N-methylated analogs [Elektronische Daten] [RAJ VAID, K BHUTANI] The steroidal alkaloid 3β, 20α-diamino-pregn-5-ene (kurchamine) obtained from the stem bark of Holarrhena antidysenterica is reported to have appreciable amoebicidal activity. Its three stereoisomers namely 3α, 20β-diamino-pregn-5-ene, 3β, 20β-diamino-pregn-5-ene and 3α,20α-diamino-pregn-5-ene and their intermediate stereoisomeric monoamino pregnene alkaloids namely 3β-amino-pregn-5-ene-20-one, 3α-amino-pregn-5-ene-20-one, 20α -amino-pregn-5-ene-3β-ol, 20β-amino-pregn-5-ene-3β-ol were synthesized. The natural stereoisomer and synthesized diamino and monoamino stereoisomers were N-methylated and all the compounds were evaluated for amoebicidal activity comparison. The natural stereoisomer 3β,20α-diamino-pregn-5-ene (kurchamine) was found to be superior than other stereoisomers and N-methylation was found to have insignificant effect on amoebicidal activity of stereoisomers. Graphical Abstract Stereoisomers of kurchamine, the natural pregnene alkaloid of Holarrhena antidysenterica (stem bark) and their intermediate monoamino stereoisomers were synthesized from 16-dehydropregnenolone acetate (16-DPA). Kurchamine and synthesized stereoisomers along with their N-methylated analogs were evaluated for their antiamoebic activity. Indian Academy of Sciences, 2013 Holarrhena antidysenterica nationallicence amoebiasis nationallicence kurchamine nationallicence conessine nationallicence diamino pregnene nationallicence monoamino pregnene nationallicence stereoisomers nationallicence VAID RAJ Organic Chemistry Division, Regional Research Laboratory, Indian Institute of Integrative Medicine (IIIM), Canal Road, 180 001, Jammu, India aut BHUTANI K. National Institute of Pharmaceutical Education and Research, (NIPER), Sector 67, SAS Nagar, 160 062, (Mohali), India aut Journal of Chemical Sciences Springer-Verlag 125/1(2013-01-01), 183-185 0974-3626 125:1<183 2013 125 12039 https://doi.org/10.1007/s12039-012-0346-x text/html Onlinezugriff via DOI 1 brief-communication jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s12039-012-0346-x text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- VAID RAJ Organic Chemistry Division, Regional Research Laboratory, Indian Institute of Integrative Medicine (IIIM), Canal Road, 180 001, Jammu, India aut NATIONALLICENCE 700 1- BHUTANI K. National Institute of Pharmaceutical Education and Research, (NIPER), Sector 67, SAS Nagar, 160 062, (Mohali), India aut NATIONALLICENCE 773 0- Journal of Chemical Sciences Springer-Verlag 125/1(2013-01-01), 183-185 0974-3626 125:1<183 2013 125 12039 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer