158938-08-0

Basic information

• Product Name: [1,1':4',1''-Terphenyl]-4-carboxylic acid, 4''-(pentyloxy)-
• Synonyms: [1,1':4',1''-Terphenyl]-4-carboxylic acid, 4''-(pentyloxy)-;4-(4''-pentyloxy-1,1':4',1''-terphenyl)-carboxylic acid;4''-(pentyloxy)-[1,1':4',1''-Terphenyl]-4-carboxylic acid
• CAS NO: 158938-08-0
• Molecular Formula: C₂₄H₂₄O₃
• Molecular Weight: 360.45
• EINECS: 691-410-4
• Mol File: 158938-08-0.mol

Chemical Properties

• Boiling Point: 557.9±43.0 °C(Predicted)
• Appearance: /
• Density: 1.117
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.23±0.10(Predicted)
• CAS DataBase Reference: [1,1':4',1''-Terphenyl]-4-carboxylic acid, 4''-(pentyloxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: [1,1':4',1''-Terphenyl]-4-carboxylic acid, 4''-(pentyloxy)-(158938-08-0)
• EPA Substance Registry System: [1,1':4',1''-Terphenyl]-4-carboxylic acid, 4''-(pentyloxy)-(158938-08-0)

Safety Data

• Hazardous Substances Data: 158938-08-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
[1,1':4',1''-Terphenyl]-4-carboxylic acid, 4''-(pentyloxy)is used as an intermediate in the synthesis of Anidulafungin (A673000), a semisynthetic echinocandin. Anidulafungin functions as an antifungal drug by inhibiting glucan synthase, an enzyme that plays a vital role in the formation of (1→3)-β-D-glucan, a major component of the fungal cell wall. This inhibition disrupts the integrity of the fungal cell wall, leading to the death of the fungus. The use of this compound in the pharmaceutical industry is significant for the development of effective antifungal treatments.

Upstream product

• 158937-30-5 4′′-pentyloxy-[1,1':4',1′′-terphenyl]-4-carboxylic acid methyl ester 
• 14047-29-1 4-carboxyphenylboronic acid 
• 63619-51-2 4-bromo-4'-pentyloxybiphenyl 
• 628-17-1 amyl iodide 
• 29558-77-8 4-bromo-4'-hydroxybiphenyl 
• 619-44-3 methyl 4-iodobenzoate 
• 158937-25-8 4-(4-n-pentyloxyphenyl)phenylboronic acid 
• 619-58-9 4-iodobenzoic acid 
• 5731-12-4 4’-iodo-[1,1’-biphenyl]-4-carboxylic acid 
• 146449-90-3 [4-(pentyloxy)phenyl]boronic acid 
• 289706-68-9 4-n-pentoxyphenylboronic acid ethylene glycol ester 
• 110-53-2 1-Bromopentane 
• 106-37-6 1.4-dibromobenzene 
• 4612-26-4 1,4-Phenyldiboronic acid 

Downstream Products

• 158937-65-6 2,4,5-trichlorophenyl 4-(4'-pentyloxybiphenyl)benzoate 
• 1345195-40-5 C₈₃H₁₁₈N₈O₁₆ 
• 1345195-46-1 C₆₁H₇₆N₈O₁₄ 
• 1345195-60-9 C₆₁H₇₈N₈O₁₄ 
• 1334511-82-8 C₄₅H₆₀N₄O₈ 
• 1203557-57-6 C₄₄H₅₈N₄O₉ 
• 166663-25-8 Anidulafungin 

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.

Preparation method of anidulafungin intermediate

The invention belongs to the technical field of drug synthesis, and particularly relates to a preparation method of an anidulafungin intermediate. The preparation method includes the steps of (1), subjecting iodobenzoic acid and 1,4-indole-dibenzoboronic acid pinacol ester to reaction in a solvent in the presence of palladium and alkali; (2), adding 4-p-(pentyloxy) iodobenzene to reaction liquid of the step (1) to obtain 4''-(pentyloxy)-[1,1':4',1''-Terphenyl]-4-carboxylic acid, namely the anidulafungin intermediate. The preparation method is easy in operation and high in yield and capable ofmeeting requirements on industrial production.

Unified Protocol for Fe-Based Catalyzed Biaryl Cross-Couplings between Various Aryl Electrophiles and Aryl Grignard Reagents

The combination of commonly used FeCl3/SIPr with Ti(OEt)4/PhOM enabled a highly general iron-based catalyst system, which could efficiently catalyze the biaryl coupling reaction between various electrophiles (I, Br, Cl, OTs, OCONMe2, OSO2NMe2) and common or functionalized aryl Grignard reagents with high functional group tolerance. Selective couplings of aryl iodides and bromides over the corresponding oxygen-based electrophiles have been achieved, and thus a terphenyl acid intermediate for anidulafungin was conveniently synthesized via an orthogonal coupling strategy.

Preparation method for synthesizing anidulafungin intermittent ([1,1':4',1''-Terphenyl]-4-carboxylic acid, 4''-(pentyloxy)-) through one-step method

The invention belongs to the field of compound preparation and discloses a preparation method for synthesizing an anidulafungin intermittent ([1,1':4',1''-Terphenyl]-4-carboxylic acid, 4''-(pentyloxy)-) through a one-step method. The method comprises the following steps: under a condition of an alkali solution, by taking N,N-dimethyl formamide as a solvent, catalyzing with a palladium catalyst, adding 4-bromobenzoic acid, 1,4-phenylenediboronic acid pinacol ester and 4-(n-pentyloxy) bromobenzene as raw materials, and performing an SUZUKI coupling reaction, thereby obtaining a target product, namely the anidulafungin intermittent ([1,1':4',1''-Terphenyl]-4-carboxylic acid, 4''-(pentyloxy)-). The raw materials used in the method are all industrial products available in the market, the raw materials are easily available, in addition, the steps are simple, the reaction conditions can be controlled, wastes are greatly reduced in the production process of the product, and chemical environmental-friendly requirements of the current society are met.

Off-axis digital holographic microscope as described in any one of Claims 1 to 6, includes a light coupled to the target unit (Sa) fluorescence excitation source (17).

The invention belongs to the field of medicine synthesis and specifically relates to a preparation method of an anidulafungin side chain intermediate 4'-orthopentyloxy-1,1':4',1'-terphenyl-4-carboxylic acid. The preparation method comprises the following steps: initiating a 1,4-dibromo-benzene material which serves as a starting material to carry out Grignard reagent reaction with magnesium by iodine; then, preparing 1,4-benzene hypoboric acid by virtue of addition and hydrolysis with trimethyl borate; and preparing 4'-orthopentyloxy-1,1':4',1'- terphenyl-ethyl carboxylate by virtue of Suzuki reaction of 1,4-benzene hypoboric acid, 4-pentyloxy bromobenzene and 4-halogenated ethyl benzoate in dioxane-ethanol liquor under catalysis of [1,1'-bis(diphenyl phosphino) ferrocene] palladium dichloride, and then, hydrolyzing to obtain a target product. The preparation method disclosed by the invention can lower process cost, is simple, convenient, safe and reliable to operate, and suitable for industrial production.

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

Discovery, SAR, synthesis, pharmacokinetic and biochemical characterization of A-192411: A novel fungicidal lipopeptide-(I)

The echinocandin class of cyclic lipopepetides has been simplified to discover potent antifungal compounds. Namely A-192411 shows good in vitro activity against common pathogenic yeasts and has an acceptable safety window in vivo. Discovery, limited SAR, synthesis, biochemical and pharmaco-dynamic profiles of A-192411 are presented.

Cyclohexapeptidyl aminoalkyl ethers

There are disclosed compounds of the general formula STR1 wherein all substituents are defined herein. The compounds are useful as antibiotic and antifungal agents.

Antifungal cyclohexapeptides

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.