1428382-55-1Relevant articles and documents
Synthesis of novel 16-spiro steroids: Spiro-7′-(aryl)tetrahydro-1H- pyrrolo[1,2-c][1,3]thiazolo-trans-androsterone hybrid heterocycles
Kanchithalaivan, Selvaraj,Kumar, Raju Ranjith,Perumal, Subbu
, p. 409 - 417 (2013)
The 1,3-dipolar cycloaddition of azomethine ylide derived in situ from the reaction of acenaphthylene-1,2-dione and 1,3-thiazolane-4-carboxylic acid to various exocyclic dipolarophiles synthesized from trans-androsterone and trans-dehydroandrosterone afforded a library of novel spiro[5′.2″] acenaphthylene-1″-one-spiro[16.6′]-(7′-aryl) -tetrahydro-1H-pyrrolo [1,2-c][1,3]thiazolo-trans-androsterone/ dehydroandrosterone hybrid heterocycles respectively. These reactions proceeded stereo-specifically affording a single isomer of the 16-spiro steroids in excellent yields.
Design, synthesis and biological evaluation of novel steroidal spiro-oxindoles as potent antiproliferative agents
Yu, Bin,Shi, Xiao-Jing,Qi, Ping-Ping,Yu, De-Quan,Liu, Hong-Min
, p. 121 - 134 (2014/03/21)
Two series of novel steroidal spiro-pyrrolidinyl oxindoles 3a-t and 6a-c were designed and synthesized from dehydroepiandrosterone using the 1,3-dipolar cycloaddition as the key step and further evaluated for their antiproliferative activities for four human cancer cell lines (MGC-803, EC109, SMMC-7721 and MCF-7). This protocol achieved the formation of two CC bonds, one CN bond and the creation of one new five-membered pyrrolidine ring and three contiguous stereocenters in a single operation. Biological evaluation showed that these synthesized steroidal spiro-pyrrolidinyl oxindoles possessed moderate to good antiproliferative activities against the tested cell lines and some of them were more potent than 5-Fu. Particularly, compound 3g showed good antiproliferative activity against SMMC-7721 (IC50 = 0.71 μM). Steroid dimer 6b showed improved antiproliferative activities against SMMC-7721 and MCF-7 with the IC50 values of 4.30 and 2.06 μM, respectively. Flow cytometry analysis demonstrated that compound 3n caused the cellular early apoptosis and cell cycle arrest at G2/M phase in a concentration- and time-independent manner.