179162-64-2

Usage

Uses

Used in Pharmaceutical Industry:
Micafungin Side Chain Methyl Ester is used as a key intermediate in the synthesis of new drug candidates for enhancing their antifungal properties. Its improved stability and bioavailability contribute to the development of more effective medications against fungal infections.
Used in Drug Development:
Micafungin Side Chain Methyl Ester is utilized as a valuable tool in drug development, allowing researchers to create antifungal medications with better pharmacokinetic and pharmacodynamic profiles. This leads to the production of drugs that are more potent, have longer-lasting effects, and are better absorbed by the body, ultimately improving treatment outcomes for patients suffering from fungal infections.

InChI:InChI=1/C22H23NO4/c1-3-4-5-14-26-19-12-10-17(11-13-19)21-15-20(23-27-21)16-6-8-18(9-7-16)22(24)25-2/h6-13,15H,3-5,14H2,1-2H3

Upstream product

• 79887-16-4 1-ethynyl-4-(pentyloxy)benzene 
• 101023-70-5 4-methoxycarbonylbenzhydroxamic acid chloride 
• 99-93-4 4-Hydroxyacetophenone 
• 110-53-2 1-Bromopentane 
• 5467-56-1 4-pentyloxyacetophenone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 5736-91-4 4-(n-pentyloxy)benzaldehyde 
• 1571-08-0 methyl 4-formylbenzoate 
• 1431323-57-7 C₁₃H₁₆ClNO₃ 
• 1679-64-7 Monomethyl terephthalate 

Downstream Products

• 235112-66-0 1-[[4-[5-(4-pentyloxyphenyl)isoxazol-3-yl]benzoyl]oxy]-1H-1,2,3-benzotriazole 
• 179162-55-1 4-{5-[4-(pentyloxy)phenyl]-1,2-oxazol-3-yl}benzoic acid 

Relevant academic research and scientific papers

Synthesis method of micafungin side chain intermediate

The invention discloses a synthesis method of a micafungin side chain intermediate. An important side chain intermediate for synthesizing micafungin can be obtained through only three steps, and the steps are simple. Firstly, 4-pentoxyl acetophenone and methyl p-formylbenzoate as initial raw materials are subjected to an aldol condensation reaction under the action of an alkali catalyst cesium carbonate to obtain an intermediate M1; then, the intermediate M1 and N-hydroxyl p-toluenesulfonamide are cyclized under the action of the alkali catalyst cesium carbonate to obtain an intermediate M2; and finally, transesterification reaction is carried out on the intermediate M2 and 1-hydroxybenzotriazole to obtain the high-purity micafungin side chain intermediate shown in the formula M (See the specification). A brand-new synthesis route is provided, and a foundation is laid for preparation of a final product micafungin.

A concise synthesis of isoxazole-based side chain of Micafungin

A concise synthesis of key isoxazole-based side chain of Micafungin, an USFDA approved anti-fungal agent, has been delineated. The route design notably involves a one pot regioselective isoxazole construction from the corresponding aryl aldehyde and alkyne intermediates.

Synthesis and antifungal evaluation of pentyloxyl-diphenylisoxazoloyl pneumocandins and echinocandins

Echinocandins and pneumocandins are classes of lipocyclohexapeptides that are broad spectrum antifungal agents. They inhibit fungal specific 1,3-β-glucan synthase activity which is an essential component of the fungal cell wall. Chemical modifications of

Novel echinocandin antifungals. Part 2: Optimization of the side chain of the natural product FR901379. Discovery of micafungin

Further optimization of the potent antifungal activity of side chain analogs of the natural product FR901379 led to the discovery of compound 8 with an excellent, well-balanced profile. Potent compounds with reduced hemolytic potential were designed based upon a disruption of the linearity of the terphenyl lipophilic side chain. The optimized compound (8, FK463, micafungin) displayed the best balance and was selected as the clinical candidate.

Practical synthesis of FR195752, the side chain of Micafungin, utilizing a regioselective conversion of diaryl-β-diketone to 3,5-diarylisoxazole

The practical synthesis of FR195752, the side chain of Micafungin, was established utilizing a highly regioselective conversion of diaryl-β- diketone to 3,5-diarylisoxazole via the corresponding β-keto enamine intermediate whose disfavored regioisomer could be recycled efficiently after its hydrolysis. In addition, the related substance of FR195752 could be strictly controlled by the purification of its intermediate.

Novel manufacturing method

The present invention relates to a novel process for preparing of the compound of the following formula (I) Thus, the process for preparing of a compound of the formula (I): [Wherein R1 is carboxy or protected carboxy; R2 is lower alkoxy or higher alkoxy; A1 is divalent aromatic ring, divalent heterocyclic group or divalent cyclo(lower)alkane; and A2 is divalent aromatic ring, divalent heterocyclic group or divalent cyclo(lower)alkane], or a salt thereof, which comprises, reacting a compound of the formula (III): [Wherein R1, R2, A1 and A2 are each as defined above] or a salt thereof, with an acid ammonium salt to give a compound of the formula (II): [Wherein R1, R2, A1 and A2 are each as defined above] or a salt thereof, further reacting with hydroxylamine salt.