7591-17-5

Upstream product

• 70864-97-0 6β-bromo-5α-cholestane-3β,7β-diol 
• 70864-96-9 6α-bromo-5α-cholestane-3β,7α-diol 
• 566-28-9 7-Oxocholesterol 
• 782477-92-3 3β-[(tetrahydropyran-2-yl)oxy]-cholestan-7-one 
• 6038-71-7 3β-acetoxy-5α-cholestan-7-one 
• 809-51-8 7-ketocholesteryl acetate 
• 57-88-5 cholesterol 
• 6252-45-5 3-O-(tetrahydro-2H-pyran-2-yl)cholesterol 
• 164120-23-4 3β-<(tetrahydropyran-2-yl)oxy>-7-oxo-cholest-5-ene 
• 70865-00-8 3β-acetoxy-6β-bromo-5α-cholestan-7-one 
• 70864-92-5 3β-acetoxy-6α-bromo-5α-cholestan-7-one 

Downstream Products

• 17150-36-6 3β-tosyloxy-5α-cholestan-7-one 
• 13400-67-4 3,7-dioxo-5α-cholestane 
• 80-97-7 Cholestanol 

Relevant academic research and scientific papers

Inhibitory effect of oxygenated cholestan-3-ol derivatives on the growth of Mycobacterium tuberculosis

A variety of cholestan-3-ol derivatives, which are oxygenated at different positions of the steroid ring system, were prepared and tested for their inhibition of the Mycobacterium tuberculosis H37Rv strain. Several compounds showed significant antitubercular activities with MIC90 values in the range 4-8 μM and low or non-detectable toxicity against mammalian cells.

Regio- and stereospecific synthesis of cholesterol derivatives and their hormonal activity in Caenorhabditis elegans

Cholesterol is essential for the survival of the nematode Caenorhabditis elegans. Recent studies have demonstrated that cholesterol derivatives regulate two processes in the life cycle of worms: controlling molting and inducing a specialized non-feeding larval stage. However, the chemical structure of the cholesterol-derived signalling molecules for these or any other functions has not yet been identified. Herein, we describe the regio- and stereospecific synthesis of a number of cholesterol derivatives. The lithium-ammonia reduction of 4-cholesten-3-one was utilized to develop a general method for the introduction of diverse functional groups at C-4α of 5α-cholestan- 3β-ol. Stereoselective functionalization at C-7 was achieved starting from 7-ketocholesterol derivatives. 6-Keto-5α-cholestan-3β-ol was utilized for specific functionalizations at C-6 and C-7. The structure-activity relationships of the different cholesterol derivatives have been investigated by feeding worms of different genetic background with these compounds. Our study is the first step in assigning the relationships of hormonal activity in C. elegans on the substitution at different positions of cholesterol. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Synthesis of spermidinylcholestanol and spermidinylcholesterol, squalamine analogues

Several novel squalamine-related polyaminosterols are reported. The synthesis of 7α-N-[3N-(4-aminobutyl)aminopropyl]aminocholestanol I, 6α-N-[3N-(4-aminobutyl)aminopropyl]aminocholestanol II, 7α and 7β-N-[3N-(4-aminobutyl)aminopropyl]aminocholesterol (III and IV), was accomplished from cholesterol, they provide the first examples in which spermidine is introduced in the B steroidal ring. These molecules showed comparable antibacteria and fungi activities to squalamine, and were cytotoxic on a human non-small cell bronchopulmonary carcinoma line (NSCLC-N6). Therefore, these molecules with antibiotic and cytotoxic activities are promising for immune-compromised patients in cancer chemotherapy. Graphical Abstract.