Synthesis and in vitro activity of oleanane type derivatives against Chlamydia trachomatis

Abstract

Modified synthesis of 3β-nicotinoyloxy-olean-12(13)-en-28-oic acid and 3-deoxy-3a-homo-3a-aza-28-hydroxy-olean-12(13)-ene from natural occurring oleanolic acid is suggested. These compounds and two others of ursane and lupane type triterpenoids (3-oximino-urs-12-en-28-oic acid and 3-deoxy-3a-homo-3a-aza-28-hydroxy-lup-12(13)-ene) were screened in vitro against Chlamydia trachomatis strain F-3271/Belarus/2015. Oleanane triterpenoids became the leading compounds with chemotherapeutic index > 8 and were chosen for further research.

Cytotoxic Potential of a-Azepano- and 3-Amino-3,4-SeCo-Triterpenoids

“…In this study, a total of 20 A-ring azepano- 1–17 and 3-amino-3,4-seco- 18–20 triterpenoids were synthesized from betulin, oleanolic, ursolic, and glycyrrhetinic acids according to methods described earlier [ 17 , 18 , 19 , 21 , 22 , 26 , 29 ]. Their structures are presented at Figure 1 , Figure 2 , Figure 3 and Figure 4 .…”

“…Among these derivatives, triterpenoids, which could be synthesized from triterpenic oximes through a Beckmann type rearrangement followed by a subsequent reduction reaction holding an A-azepane ring or a 3-amino-3,4-seco-4(24)-en-fragment are a group of new and promising modifications exhibiting anti-microbial [ 17 , 18 , 19 , 20 ], anticancer [ 21 , 22 , 23 , 24 , 25 , 26 ], alpha-glucosidase [ 27 , 28 ] as well as butyrylcholinesterase [ 29 ] inhibitory activities.…”

Evaluation of A-azepano-triterpenoids and related derivatives as antimicrobial and antiviral agents

“…Substances were detected by 10% H 2 SO 4 with subsequent heating to 100–120 °C for 2–3 min. Compounds 1 , 2 [ 57 ], 3 , 17–20 [ 24 ], 4 , 6 , 9 , 11 , 12 , 15 , 16 , 22, 23 [ 58 ], 5 [ 31 ], 7 [ 59 ], 8, 13 [ 22 ], 10 , 21 [ 30 ], 14 [ 60 ] , 25 [ 61 ], 28 [ 62 ], and 35 [ 63 ] were prepared by the literature methods. Oleanolic acid 27 was purchased from Xian RongSheng Biotechnology Co., Ltd.…”