- The synthesis and characterization of analogs of the antimicrobial compound squalamine: 6β-hydroxy-3-aminosterols synthesized from hyodeoxycholic acid
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Analogs of the aminosterol antimicrobial agent squalamine have been synthesized beginning from hyodeoxycholic acid. After carboxylic acid esterification and oxidation of both alcohol functions to ketones, the A/B ring junction was converted from cis to trans by acid-catalyzed isomerization. Different polyamines were added to the 3-keto group by reductive amination, yielding both the 3α and 3β addition products. The synthetic products exhibited potent, broad-spectrum antimicrobial activity similar to that of the parent compound. Changing the identity of the polyamine or the stereochemistry of addition has little effect upon antimicrobial activity but appears to change the selectivity of the agents. The analogs are synthesized with high yield from inexpensive starting materials and are promising alternatives to squalamine as potential antibiotics.
- Jones, Stephen R.,Kinney, William A.,Zhang, Xuehai,Jones, Lisa M.,Selinsky, Barry S.
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- Oxidation of alcohols by perfluoro-cis-2,3-dialkyl oxaziridines
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Perfluoro-cis-2,3-dialkyloxaziridines oxidize secondary alcohols 2 to the corresponding ketones 4 at room temperature. The reaction has been carried out with uniformly high yields on simple acyclic alcohols as well as more complex substrates such as α-hydroxy esters, borneols, and sterols.
- DesMarteau,Petrov,Montanari,Pregnolato,Resnati
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- Method for synthesizing lithocholic acid from hyodeoxycholic acid as raw material
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The invention discloses a method for synthesizing a lithocholic acid from a hyodeoxycholic acid as the raw material. The hyodeoxycholic acid is used as the starting material, the lithocholic acid is produced through the seven reaction steps of 24-carboxylesterification, carboxylation of 3alpha-hydroxyl and 6alpha-hydroxyl through oxidation, selective reduction, acylation, hydrazone formation, hydrazoneremoval, and hydrolysis. The starting material is cheap and easy to get, no hydrazine hydrate is used in the synthesis process, the technological conditions for synthesis are safe, environmentally friendly and mild, the total yield is relatively high, and the method is suitable for industrial production.
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- Synthetic method for 6-carbonyl lithocholic acid
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The invention discloses a synthetic method for 6-carbonyl lithocholic acid. The synthetic method comprises the following steps of by adopting hyodeoxycholic acid as a starting material, sequentially performing 4-step reaction of 24-carboxyl esterification, oxidization of 3 alpha-OH and 6 alpha-OH into carbonyl groups, selective reduction and hydrolyzation to obtain a target product. The synthetictechnology is simple in flow, liable to control, wide in raw material source and available in raw material and can realize mass production.
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- Structural modifications of deoxycholic acid to obtain three known brassinosteroid analogues and full NMR spectroscopic characterization
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An improved synthesis route for obtaining known brassinosteroid analogues, i.e., methyl 2α,3α-dihydroxy-6-oxo-5α-cholan-24-oate (11), methyl 3α-hydroxy-6-oxo-7-oxa-5α-cholan-24-oate (15) and methyl 3α-hydroxy-6-oxa-7-oxo-5α-cholan-24-oate (16), from hyodeoxycholic acid (4) maintaining the native side chain is described. In the alternative procedure, the di-oxidized product 6, obtained in the oxidation of methyl hyodeoxycholate 5, was converted almost quantitatively into the target monoketone 7 by stereoselective reduction with NaBH4 , increasing the overall yield of this synthetic route to 96.8%. The complete 1H- and 13C-NMR assignments for all compounds synthesized in this work have been made by 1D and 2D heteronuclear correlation gs-HSQC and gs-HMBC techniques. Thus, it was possible to update the spectroscopic information of 1H-NMR and to accomplish a complete assignment of all 13C-NMR signals for analogues 5-16, which were previously reported only in partial form.
- Herrera, Heidy,Carvajal, Rodrigo,Olea, Andrés F.,Espinoza, Luis
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- Microwave-assisted synthesis and in vitro antibacterial activity of novel steroidal thiosemicarbazone derivatives
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Herein, we reported the synthesis of 16 novel steroidal thiosemicarbazone derivatives via the condensation of steroidal ketones and substituted thiosemicarbazides under solvent-free conditions using microwave irradiation. The yields obtained are in the ra
- Zhao, Zhigang,Shi, Zhichuan,Liu, Min,Liu, Xingli
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p. 7730 - 7734
(2013/02/22)
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- Synthesis of new hyodeoxycholic acid thiosemicarbazone derivatives under solvent-free conditions using microwave
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An efficient and simple method for synthesis of new hyodeoxycholic acid thiosemicarbazone derivatives under solvent-free conditions using microwave has been developed. Its main advantages are short reaction times, good conversions and the environmentally friendly nature of the process. The preliminary results indicate that some of these compounds possess inhibitory effects against E. coli.
- Shi, Zhi Chuan,Zhao, Zhi Gang,Liu, Xing Li,Chen, Yu
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p. 405 - 408
(2012/01/05)
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- Selective dimethyldioxirane oxidation of bile acid methyl esters
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DMDO oxidation of the hydroxy groups of bile acid methyl esters establishes the positional order of reactivity as 3-7 > 6 > 12 and supports a mechanism involving C-H oxygen insertion through a planar intramolecularly hydrogen bonded transition state.
- Buxton, P. Christopher,Marples, Brian A.,Toon, Richard C.,Waddington, Victoria L.
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p. 4729 - 4732
(2007/10/03)
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- Method of treating a viral infection by administering a steroid compound
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A method of treating a viral infection includes administering an effective amount of a compound having the following structure: STR1 or a pharmaceutically acceptable salt thereof. This compound treats the viral infection by suppressing the growth of a viral target cell. As one specific example, this compound may be used to treat HIV infection.
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- Method of inhibiting the sodium/proton exchanger NHE3 and method of inhibiting growth by administering squalamine
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Aminosterol compounds are described that are useful as inhibitors of the sodium/proton exchanger (NHE). Methods of using such aminosterols compounds are also disclosed, including those employing compounds that are inhibitors of a spectrum of NHEs as well as those using compounds that are inhibitors of only one specific NHE. Advantageous screening techniques and assays for evaluating a compound's therapeutic activity are also disclosed.
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- Synthesis of steroids
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The synthesis of 1α,25-dihydroxycholesterol, 1α,25-dihydroxy-7-dehydrocholesterol and 1α,25-dihydroxycholecalciferol and other sterol derivatives from bile acids. Also the synthesis of 3,6-diketo steroids useful in the production of 1α,25-dihydroxycholesterol and other sterols which are biologically active or can be converted to biologically active sterols. The invention involves the sterols so produced and the processes by which they are prepared.
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