67914-85-6

Usage

Uses

Used in Pharmaceutical Industry:
cis-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolane-4-methanol is used as an intermediate in the synthesis of Itraconazole (I937500) for its antimycotic properties. Itraconazole is effective in treating various fungal infections, including aspergillosis, blastomycosis, histoplasmosis, and onychomycosis, due to its ability to inhibit the synthesis of ergosterol, an essential component of fungal cell membranes.

InChI:InChI=1/C13H13Cl2N3O3/c14-9-1-2-11(12(15)3-9)13(6-18-8-16-7-17-18)20-5-10(4-19)21-13/h1-3,7-8,10,19H,4-6H2/t10-,13-/m1/s1

Upstream product

• 288-88-0 1,2,4-Triazole 
• 61397-56-6 (+/-)-cis-[2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane-4-yl]methyl benzoate 
• 2234-16-4 1-(2,4-dichlorophenyl)ethan-1-one 
• 172032-21-2 (2-(2,4-dichlorophenyl)-2-methyl-1,3-dioxolan-4-yl)methanol 
• 68751-57-5 2-(2,4-dichlorophenyl)-2-bromomethyl-4-hydroxymethyl-1,3-dioxolane 
• 67914-84-5 Benzoic acid (2R,4R)-2-(2,4-dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethyl ester 

Downstream Products

• 67915-31-5 (+/-)-Terconazole 
• 113770-65-3 Toluene-4-sulfonic acid (2R,4R)-2-(2,4-dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethyl ester 
• 67914-86-7 cis-[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate 

Relevant academic research and scientific papers

Prepartion method of itraconazole

The invention discloses a preparation method of itraconazole. Raceme-glycidol which is cheap and easy to obtain is adopted as raw materials, hydroxyls at the two ends are protected by trityl and benzyl and then esterified by 2,4-dichlorobenzene formyl chloride, then, a silylation Grignard addition reaction and a beta-silicyl alcohol elimination reaction are adopted for reducing carbonyl into carbon-carbon double bonds, iodine is adopted for performing an olefin addition reaction and a stereoselectivity ring-closure reaction, triazole replacement and debenzylation are performed, and tosyl is introduced to obtain a compound 9; the compound and a compound 10 are subjected to a condensastion reaction to obtain itraconazole; the overall synthesis process is small in pollution, easy to process, few in by-product, high in reaction selectivity and purity, environmentally friendly, low in production cost and suitable for industrial production; the defects that in the prior art, the selectivity is poor, multiple by-products are produced, the yield is low, and expensive catalysts and reagents with large environmental pollution are avoided are avoided.

Synthesis, antifungal activity and structure-activity relationships of 2-(alkyl or aryl)-2-(alkyl or polyazol-1-ylmethyl)-4-(polyazol-1-ylmethyl)- 1,3-dioxolanes

A series of 2-(alkyl or aryl)-2-(alkyl or polyazol-1-ylmethyl)-4-(polyazol-1-ylmethyl)-1,3-dioxolanes Ia-u was synthesized and tested in vitro against pathogenic fungi in man, animals and plants: Candida albicans, Aspergillus flavus and Fusarium solani. Compounds Iq-t with two polyazol groups have an in vitro activity against these fungi with MIC (minimum inhibitory concentration) value of 5 μg mL-1.

Antimycotic Azoles. 6. Synthesis and Antifungal Properties of Terconazole, a Novel Triazole Ketal

The preparation and antifungal properties of cis-1-methoxy>phenyl>-4-(1-methylethyl)piperazine are reported.Terconazole has a high topical in vivo activity against vaginal candidosis in rats and against dermatophytosis in guinea pigs.