158937-30-5

Basic information

• Product Name: 4''-(Pentyloxy)-[1,1':4',1''-terphenyl]-4-carboxylic acid methyl ester
• Synonyms: 4''-(Pentyloxy)-[1,1':4',1''-terphenyl]-4-carboxylic acid methyl ester
• CAS NO: 158937-30-5
• Molecular Formula: C₂₅H₂₆O₃
• Molecular Weight: 374.47214
• Mol File: 158937-30-5.mol

Chemical Properties

• Appearance: /
• Density: 1.076±0.06 g/cm3 (20 ºC 760 Torr)
• CAS DataBase Reference: 4''-(Pentyloxy)-[1,1':4',1''-terphenyl]-4-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4''-(Pentyloxy)-[1,1':4',1''-terphenyl]-4-carboxylic acid methyl ester(158937-30-5)
• EPA Substance Registry System: 4''-(Pentyloxy)-[1,1':4',1''-terphenyl]-4-carboxylic acid methyl ester(158937-30-5)

Safety Data

• Hazardous Substances Data: 158937-30-5(Hazardous Substances Data)

Upstream product

• 289706-68-9 4-n-pentoxyphenylboronic acid ethylene glycol ester 
• 158407-15-9 methyl 4’-iodo-[1,1’-biphenyl]-4-carboxylate 
• 63619-51-2 4-bromo-4'-pentyloxybiphenyl 
• 29558-77-8 4-bromo-4'-hydroxybiphenyl 
• 110-53-2 1-Bromopentane 
• 158937-25-8 4-(4-n-pentyloxyphenyl)phenylboronic acid 
• 619-44-3 methyl 4-iodobenzoate 

Downstream Products

• 1203557-57-6 C₄₄H₅₈N₄O₉ 
• 1334511-82-8 C₄₅H₆₀N₄O₈ 
• 166663-25-8 Anidulafungin 
• 158937-65-6 2,4,5-trichlorophenyl 4-(4'-pentyloxybiphenyl)benzoate 
• 158938-08-0 4′′-(pentyloxy)-1,1′:4′,1′′-terphenyl-4-carboxylic acid 

Relevant articles and documents

Anidulafungin side chain intermediate 4''-(pentyloxy)-[1,1':4',1''-terphenyl]-4-carboxylic acid

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.

Total synthesis and structure-activity relationships of new echinocandin-like antifungal cyclolipohexapeptides

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.

METHOD FOR PRODUCING (1,1':4'1'')-TERPHENYL COMPOUNDS

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

Semisynthetic Chemical Modification of the Antifungal Lipopeptide Echinocandin B (ECB): Structure-Activity Studies of the Lipophilic and Geometric Parameters of Polyarylated Acyl Analogs of ECB

Echinocandin B (ECB) is a lipopeptide composed of a complex cyclic peptide acylated at the N-terminus by linoleic acid.Enzymatic deacylation of ECB provided the peptide "nucleus" as a biologically inactive substrate from which novel ECB analogs were generated by chemical reacylation at the N-terminus.Varying the acyl group revealed that the structure and physical properties of the side chain, particularly its geometry and lipophlicity, played a pivotal role in determining the antifungal potency properties of the analog.Using CLOGP values to describe and compare the lipophlicities of the side chain fragments, it was shown that values of >3.5 were required for expression of antifungal activity.Sercondly, a linearly rigid geometry of the side chain was the most effective shape in enhancing the antifungal potency.Using these parameters as a guide, a variety of novel ECB analogs were synthesized which included arylacyl groups that incorporated biphenyl, terphenyl, tetraphenyl, and arylethynyl groups.Generally the glucan synthase inhibition by these analogs correlated well with in vitro and in vivo activities and was likewise influenced by the structure of the side chain.These structural variations resulted in enhancement of antifungal activity in both in vitro and in vivo assays.Some of these analogs, including LY303336 (14a), were effective by the oral route of administartion.