63619-51-2

Upstream product

• 628-17-1 amyl iodide 
• 29558-77-8 4-bromo-4'-hydroxybiphenyl 
• 78-93-3 butanone 
• 110-53-2 1-Bromopentane 

Downstream Products

• 158937-30-5 4′′-pentyloxy-[1,1':4',1′′-terphenyl]-4-carboxylic acid methyl ester 
• 158937-25-8 4-(4-n-pentyloxyphenyl)phenylboronic acid 
• 1334511-82-8 C₄₅H₆₀N₄O₈ 
• 1203557-57-6 C₄₄H₅₈N₄O₉ 
• 59748-15-1 4'-n-pentyloxybiphenyl-4-carboxylic acid 
• 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 
• 52364-71-3 4'-(pentyloxy)-4-biphenylcarbonitrile 

Relevant academic research and scientific papers

Novel echinocandin antifungals. Part 1: Novel side-chain analogs of the natural product FR901379

A series of novel acylated analogs of the novel water-soluble echinocandin FR901379 have been prepared and evaluated for antifungal and hemolytic activity. A relationship between antifungal activity and lipophilicity of the acyl side chain, expressed as Clog P was demonstrated, and an analog (3c) with 5.5- to 8-fold superior in vivo activity relative to the previously disclosed 4-(n-octyloxy)benzoyl side chain analog, FR131535 obtained.

Fascinating phenomena towards single-component white-light emission through luminescent thermochromism

Developing broad spectrum white-light emitting materials was always considered a challenge in terms of color stability and reproducibility. Here, we report the design and optical properties of two materials bearing an ethynylbiphenyl group. The two materials exhibited excellent thermal stability and showed liquid crystal (LC) behavior. Promisingly, temperature-dependent photoluminescence results demonstrated distinct thermochromic behavior which switches the emission color from deep blue in the crystal phase to white in the LC phase. It was revealed that the overall effect of the intermolecular interactions forming a new excited state in the LC phase of the ethynylbiphenyl moiety is the main cause for the white-light emission. The emission behavior of the studied materials was tuned by thermal stimuli, and the emission color was regulated by changing the aggregate structure. These present findings open a door to develop more appealing single-molecule white-light emitters.

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.

Synthesis of liquid crystal molecules based on bis(biphenyl)diacetylene and their liquid crystallinity

We synthesized novel liquid crystalline molecules that contain a bis(biphenyl)diacetylene mesogen and confirmed their structures by 1HNMR, 13CNMR, and FT-IR spectroscopy and mass spectrometry. These compounds formed thermotropic liquid crystals in a wide temperature region that was well characterized by optical microscopic and X-ray measurements.

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.

Echinocandin pharmaceutical formulations containing micelle-forming surfactants

Pharmaceutical formulations are described comprising an echinocandin compound or echinocandin/carbohydrate complex and a pharmaceutically acceptable micelle-forming surfactant in a non-toxic aqueous solvent such that the solubilization of the echinocandin compound is optimized and the ability to freeze-dry the solution is maintained. Both the solution and freeze-dried formulations have increased stability. A bulking agent, tonicity agent buffer and/or a stabilizing agent may optionally be added to the formulations to further enhance the stability of the formulation.

Processes for making pharmaceutical oral ECB formulations and compositions

A fluid bed spray process is described where one or more carbohydrates are incorporated into an echinocandin formulation to provide a significant improvement in thermal stability. The carbohydrate is solubilized with an echinocandin compound or echinocandin/carbohydrate complex in a solvent(s) to form a pharmaceutical solution which is sprayed onto the surface of a granular diluent or carrier. Alternatively, a granulating agent is added to the pharmaceutical solution which is then sprayed onto the surface of a non-granular diluent or carrier. The resulting granular oral formulations and medicaments derived therefrom are also described.

Echinocandin/carbohydrate complexes

A complex of an echinocandin compound with a carbohydrate is described having improved thermal stability and water solubility. A process for making the echinocandin/carbohydrate complex is also described as well as the use of the complex in pharmaceutical formulations and treatments of fungal infections.

Cyclohexapeptidyl amine compounds

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.