1164-81-4

Usage

InChI:InChI=1/C21H29ClO2/c1-12(23)14-6-7-15-13-4-5-17-19(22)18(24)9-11-21(17,3)16(13)8-10-20(14,15)2/h13-16H,4-11H2,1-3H3/t13-,14+,15-,16-,20+,21+/m0/s1

Upstream product

• 17597-24-9 (4β,5)-epoxy-5β-pregnan-3,20-dione 
• 7647-01-0 hydrogenchloride 
• 64-19-7 acetic acid 
• 1164-27-8 4(α,β),5-epoxypregnyne-3,20-dione 
• 57-83-0 Progesterone 

Downstream Products

• 1448329-09-6 21E-benzylidene-4-chloropregn-1,4-diene-3,20-dione 
• 1448329-10-9 21E-(2-chlorobenzylidene)-4-chloro-pregn-1,4-diene-3,20-dione 
• 1448329-11-0 21E-(4-chlorobenzylidene)-4-chloropregn-1,4-diene-3,20-dione 
• 1448329-12-1 21E-(2-methoxybenzylidene)-4-chloropregn-1,4-diene-3,20-dione 
• 1448329-13-2 21E-(4-methoxybenzylidene)-4-chloropregn-1,4-diene-3,20-dione 
• 1448329-14-3 21E-(2-nitrobenzylidene)-4-chloropregn-1,4-diene-3,20-dione 
• 1448329-15-4 21E-(4-methylbenzylidene)-4-chloropregn-1,4-diene-3,20-dione 

Relevant academic research and scientific papers

Multiple Enone-Directed Reactivity Modes Lead to the Selective Photochemical Fluorination of Polycyclic Terpenoid Derivatives

In the realm of aliphatic fluorination, the problem of reactivity has been very successfully addressed in recent years. In contrast, the associated problem of selectivity, that is, directing fluorination to specific sites in complex molecules, remains a great, fundamental challenge. In this report, we show that the enone functional group, upon photoexcitation, provides a solution. Based solely on orientation of the oxygen atom, site-selective photochemical fluorination is achieved on steroids and bioactive polycycles with up to 65 different sp3 C-H bonds. We have also found that γ-, β-, homoallylic, and allylic fluorination are all possible and predictable through the theoretical modes reported herein. Lastly, we present a preliminary mechanistic hypothesis characterized by intramolecular hydrogen atom transfer, radical fluorination, and ultimate restoration of the enone. In all, these results provide a leap forward in the design of selective fluorination of complex substrates that should be relevant to drug discovery, where fluorine plays a prominent role.

Potential insecticidal activity of steroidal U-17 pyrazolinyl derivatives

Agrochemical research, over the last two decades, has resulted in the discovery of chemically novel insecticides, of which steroids-based compounds that mimic the action of hormones have been considered as safe insecticides. In this study, eight steroidal C-17 pyrazolinyl derivatives were resynthesized through molecular hybridization and their insecticidal activities against 4th instar larvae of Mythimna separate were evaluated. These results showed that some compounds exhibited significant insecticidal activities and the susceptibility assays were expressed as the median lethal dose (LD50), of which one of the compounds exerted the most potent insecticidal activity (LD50 = 296 μg g-1), comparable to that of the natural product insecticide, celangulatin V (LD50 = 260 μg g-1). This strategy led to a promising candidate for the development of new steroidal insecticidal agents.

Synthesis and cytotoxic activity of some novel steroidal C-17 pyrazolinyl derivatives

Fourteen novel steroidal C-17 pyrazolinyl derivatives 9a-g and 10a-g were synthesized from commercially available progesterone and tested for their cytotoxic activity against brine shrimp (Artemia salina) and three human cancer cell lines (NCI-H460, HeLa, and HepG2). Some of these synthetic compounds exhibited significant cytotoxic activity, and treatment of HeLa cells with compound 10b resulted in the cell population arrest in the S phase. A structure-activity relationship was discussed.

Synthesis and cytotoxicity of some novel 21E-benzylidene steroidal derivatives

A series of novel derivatives of 21E-benzylidene-pregn-1,4-diene-3,20-dione 7a-g and 21E-benzylidene-4-chloro-pregn-1,4-diene-3,20-dione 8a-g was synthesized from the commercially available progesterone. These title compounds were evaluated for their cyto