1414928-38-3

Basic information

• Product Name: 3-acetyl-N-[(2R)-1-{4-[(2β,3α,5α,20R)-3,20-dihydroxypregnan-2-yl]piperazin-1-yl}-1-oxo-3-phenylpropan-2-yl]benzamide
• Synonyms: 3-acetyl-N-[(2R)-1-{4-[(2β,3α,5α,20R)-3,20-dihydroxypregnan-2-yl]piperazin-1-yl}-1-oxo-3-phenylpropan-2-yl]benzamide
• CAS NO: 1414928-38-3
• Molecular Weight: 697.959
• Mol File: 1414928-38-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-acetyl-N-[(2R)-1-{4-[(2β,3α,5α,20R)-3,20-dihydroxypregnan-2-yl]piperazin-1-yl}-1-oxo-3-phenylpropan-2-yl]benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-acetyl-N-[(2R)-1-{4-[(2β,3α,5α,20R)-3,20-dihydroxypregnan-2-yl]piperazin-1-yl}-1-oxo-3-phenylpropan-2-yl]benzamide(1414928-38-3)
• EPA Substance Registry System: 3-acetyl-N-[(2R)-1-{4-[(2β,3α,5α,20R)-3,20-dihydroxypregnan-2-yl]piperazin-1-yl}-1-oxo-3-phenylpropan-2-yl]benzamide(1414928-38-3)

Safety Data

• Hazardous Substances Data: 1414928-38-3(Hazardous Substances Data)

Upstream product

• 1414927-96-0 (2α,3α,5α,20R)-2,3-epoxypregnan-20-ol 
• 19290-93-8 (5α,20R)-pregn-2-en-20-ol 
• 586-42-5 3-acetylbenzoic acid 
• 1414927-98-2 9H-fluoren-9-ylmethyl-4-[(2b,3a,5a,20R)-3,20-dihydroxypregnan-2-yl]piperazine-1-carboxylate 
• 86123-10-6 Fmoc-D-Phe-OH 
• 969-72-2 5α-pregn-2-en-20-one 
• 516-55-2 isopregnanolone 

Relevant articles and documents

Solid-phase chemical synthesis and in vitro biological evaluation of novel 2β-piperazino-(20R)-5α-pregnane-3α,20-diol N-derivatives as anti-leukemic agents

The steroid nucleus is an interesting scaffold for the development of new therapeutic agents. Within the goal of identifying anticancer agents, new pregnane derivatives were prepared by using a sequence of liquid and solid-phase reactions. After we dehydrated epi-allopregnanolone in one step with diethylaminosulfur trifluoride and generated a 2,3α-epoxide, the regio- and stereo-selective aminolysis of this epoxide enabled us to obtain a 2β-piperazino-pregnane, whose secondary amine was protected as N-Fmoc-derivative. Using the difference in reactivity between OHs 3 and 20, we linked the pregnane nucleus-selectively on the polystyrene diethylbutylsilane resin via the OH in position 20. We next achieved in parallel the coupling of an amino acid (1st level of diversity) and the coupling of a carboxylic acid (2nd level of diversity) to generate two libraries of pregnane derivatives. The compounds inhibited the HL-60 leukemia cell growth and the most potent were three compounds (PD, LPC-37 and LPC-48) with a l-proline as first level of diversity and a cyclohexyl-carbonyl, a naphthalene-2-carbonyl or a 3-acetylbenzoyl as second level of diversity. LPC-48 efficiently inhibited HL-60 cell proliferation with IC50 value of 1.9 μM and exhibited a low toxicity on normal peripheral blood lymphocytes (IC50 = 31 μM). These results encouraged us to further evaluate the biological activity of these new aminosteroids by investigating their preliminary mechanism of action.