- Anidulafungin side chain intermediate 4''-(pentyloxy)-[1,1':4',1''-terphenyl]-4-carboxylic acid
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The invention relates to the preparation method of anidulafungin side chain intermediate 4''-(pentyloxy)-[1,1':4',1''-terphenyl]-4-carboxylic acid. The preparation method includes the steps of S1, subjecting 4 hydroxy-4'-bromobiphenyl and 1-bromopentane to nucleophilic substitution to obtain 4'-bromo-4-n-amyloxybiphenyl; S2, subjecting the 4'-bromo-4-n-amyloxybiphenyl and tetrahydroxydiboron to Suzuki coupling reaction to obtain 4-pentyloxy-4'-biphenylboronic acid; S3, subjecting the 4-pentyloxy-4'-biphenylboronic acid and methyl 4-iodobenzoate to Suzuki coupling reaction to obtain methyl 4''-(pentyloxy)-[1,1',4'-1''-terphenyl]-4-formate; S4, hydrolyzing to obtain 4''-(pentyloxy)-[1,1':4',1''-terphenyl]-4-carboxylic acid. arylboronic acid is prepared through Suzuki coupling; the target product is then prepared through Suzuki coupling and alkali hydrolysis; the preparation method has the advantages of low cost and good process operation simplicity and safety.
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Paragraph 0063; 0066
(2019/04/17)
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- Total synthesis and structure-activity relationships of new echinocandin-like antifungal cyclolipohexapeptides
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A series of new echinocandin-like cyclolipohexapeptides were designed and total synthesized via solution phase [3 + 3]-segment coupling strategy with an attempt to improve antifungal activity. The designed compounds showed potent antifungal activities with broad spectrum. In particular, 11 compounds (i.e. 28a-e, 28g, 28i-j, 29a, 29c and 29e) showed better in vitro antifungal activities against Candida albicans or Aspergillus fumigatus than caspofungin. Moreover, the synthesized compounds provided new SAR information for the echinocandins. The findings in this work suggested that the "left" tripeptide segment of cyclolipohexapeptide scaffold might be a hydrophilic structural motif, whereas the "right" lipopeptide segment was preferred as a hydrophobic core. The amino acid component of the cyclolipohexapeptide scaffold could significantly affect the SAR of the side chains.
- Yao, Jianzhong,Liu, Hongming,Zhou, Ting,Chen, Hai,Miao, Zhenyuan,Sheng, Chunquan,Zhang, Wannian
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p. 196 - 208
(2012/07/28)
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- METHOD FOR PRODUCING (1,1':4'1'')-TERPHENYL COMPOUNDS
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The invention relates to a method for producing [1,1':4',1'']-terphenyl compounds of the formulawhich comprises reacting a metal aryl of the formulawith a boric ester at -80 to 40° C. in the presence of an inert solvent, converting the reaction product by
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- Cyclohexapeptidyl amine compounds
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Cyclohexapeptidyl amine compounds are disclosed of the formula: or its acid addition salt, wherein: R1is H or OH; R2is H or OH; R3is QCnH2nNRVRVI, QCnH2nNRVRVIRVII+Y?, or Q(CH2)1-3CRVIIIRIXNHRX. R4is H or OH; R5is H, OH or CH3; R6is H or CH3; RIis wherein Rais C1-C10alkyl; or (CH2)qNRbRcwherein Rband Rcare independently H, C1-C10alkyl or Rband Rctaken together are wherein Rdis C1-C16alkyl, phenyl or benzyl; RIIis H, C1-4alkyl or benzyl; RIIIis H, C1-4alkyl or benzyl; RIVis RIIand RIIItaken together as —(CH2)4— or —(CH2)5—; RVis H, C1-C4alkyl or benzyl; RVIis H, C1-C4alkyl or benzyl or RVand RVItogether is —(CH2)4— or —(CH2)5—; RVIIis H or C1-C4alkyl; RVIIIis H, (CH2)mH, (CH2)mOH, (CH2)mNH2or COX wherein X is NH2, OH or O(CH2)mH; RIXis H, (CH2)mH, or together with RVIIIis ═O (carbonyl); RXis H (except when RVIIIand RIXare H, C(═NH)NH2, C(═NH)CH2)0-3H, CO(CH2)0-3H, CO(CH2)mNH2, (CH2)2-4OH or (CH2)2-4NH2; Q is O or S; Y is an anion of a pharmaceutically acceptable salt each m is independently an integer from 1 to 3, inclusive; n is an integer from 2 to 4, inclusive; p is an integer from 1 to 2, inclusive and q is an integer from 2 to 4, inclusive.
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- Synthesis and property of liquid crystalline 4-alkoxyl-4″-cyano-p-terphenyls
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The synthesis of some new 4-alkoxyl-4″-cyano-p-terphenyls is described. The preliminary characterization by means of polarized optical microscopy, differential scanning calorimetry and X-ray diffraction shows that all these compounds are thermotropically liquid-crystalline and can form both the nematic and smectic mesophases.
- Zang, Zhi-Qian,Zhang, Dong,Wan, Xin-Hua,Zhou, Qi-Feng
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p. 145 - 158
(2007/10/03)
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- Cyclohexapeptidyl propanolamine compounds
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Certain propanolamine compounds are described which have a cyclohexapeptidyl nucleus and which possess antibiotic activity with physical properties suitable for direct use in therapeutic compositions. A process for their preparation is also described.
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- Cyclohexapeptidyl aminoalkyl ethers
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There are disclosed compounds of the general formula STR1 wherein all substituents are defined herein. The compounds are useful as antibiotic and antifungal agents.
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- Antifungal cyclohexapeptides
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The present invention is directed to novel carba cyclohexapeptide compounds of the formula STR1 where all substituents are defined herein, which are useful as antifungal agents and for the treatment of Pneumocystis carinii infections. Compositions containing the compounds of the invention are also disclosed.
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- Process for preparing side chain derivatives of cyclohexapeptidyl lipopeptides
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An improved process for the preparation of side chain derivatives of cyclohexapeptidyl lipopeptides represented by the formula STR1 wherein R1 is fully defined, is disclosed.
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- Aza cyclohexapeptide compounds
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The present invention relates to aza cyclohexapeptide compounds of the formula (Seq ID Nos. 1-10) STR1 which may be useful as antibiotics, antifungal agents and for the treatment of Pneumocystis carinii infections.
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- Aza cyclohexapeptide compounds
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The present invention is directed to novel aza cyclohexapeptide compounds of the formula STR1 where all substituents are defined herein, which are useful as antifungal agents and for the treatment of Pneumocystis carinii infections. Compositions containing the compounds of the invention are also disclosed.
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