126918-33-0Relevant articles and documents
METHOD FOR PRODUCING TRIAZOLE COMPOUND
-
Paragraph 0063, (2018/09/21)
PROBLEM TO BE SOLVED: To provide a novel method for producing a triazole compound useful as a pharmaceutical intermediate. SOLUTION: A production method includes reacting a lactic acid derivative with thionyl chloride, then reacting it with 1,3-difluoro benzene in the presence of Al chloride to obtain a ketone derivative, which is turned into an olefin with a Wittig reagent to be derived into compound (2), and it is then turned into an epoxy and a triazole to be derived into compound (1). SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
Optically active antifungal azoles: Synthesis and antifungal activity of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl]-ethyl} -tetrazol-2-yl/1-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol
Upadhayaya, Ram Shankar,Sinha, Neelima,Jain, Sanjay,Kishore, Nawal,Chandra, Ramesh,Arora, Sudershan K.
, p. 2225 - 2238 (2007/10/03)
A series of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl]- ethyl}-tetrazol-2-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol (11a-n) and (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl]-ethyl} -tetrazole-1-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol (12a-n) has been synthesized. The antifungal activity of compounds was evaluated by in vitro agar diffusion and broth dilution assay. Compounds 11d and its positional isomer 12d having 3-trifluoromethyl substitution on the phenyl ring of piperazine demonstrated significant antifungal activity against variety of fungal cultures (Candida spp. C. neoformans and Aspergillus spp.). The compound 12d showed MIC value of 0.12μg/mL for C. albicans, C. albicans V-01-191A-261 (resistant strain); 0.25μg/mL for C. tropicalis, C. parapsilosis ATCC 22019 and C. krusei and MIC value of 0.5μg/mL for C. glabrata, C. krusei ATCC 6258, which is comparable to itraconazole and better than fluconazole. Further, compound 11d showed significant activity (MIC; 0.25-0.5μg/mL) against Candida spp. and strong anticryptococcal activity (MIC; 0.25μg/mL) against C. neoformans.
Production methods of epoxytriazole derivative and intermediate therefor
-
Page 9, (2010/11/30)
An epoxytriazole derivative (V) useful as an intermediate for anti-fungal agents and an intermediate therefor having high quality can be produced economically and efficiently by the following industrial means. A compound of the following formula (I) is reacted with trimethyloxosulfonium salt and the like in the presence of a base to give compound (II), this compound is converted to compound (IV), and this compound is reacted with 1,2,4-triazole in the presence of a base. wherein Ar is a phenyl group optionally substituted by 1 to 3 halogen atom(s) or trifluoromethyl group, R is a hydrogen atom or lower alkyl group, and X is a leaving group.
Optically active antifungal azoles. VI. Synthesis and antifungal activity of N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl) propyl]-N′-(4-substituted phenyl)-3(2H,4H)-1,2,4-triazolones and 5(1H,4H)-tetrazolones
Kitazaki, Tomoyuki,Tamura, Norikazu,Tasaka, Akihiro,Matsushita, Yoshihiro,Hayashi, Ryogo,Okonogi, Kenji,Itoh, Katsumi
, p. 314 - 327 (2007/10/03)
A new series of optically active antifungal azoles, N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl) propyl]-N′-(4-substituted phenyl)-3(2H,4H)-1,2,4-triazolones (1,2) and 5(1H,4H)-tetrazolones (3), were prepared from the triflate derivative of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (13) by an SN2 displacement reaction with the union of an azolone (17-19) and subsequent ring-opening reaction with 1H-1,2,4-triazole. The optically active oxiranylethanol 13 was synthesized from methyl (R)-lactate in a stereocontrolled manner. The azolones 1-3 prepared showed potent antifungal activities in vitro and in vivo.
Triazole antifungals. III. Stereocontrolled synthesis of an optically active triazolylmethyloxirane precursor to antifungal oxazolidine derivatives
Konosu,Miyaoka,Tajima,Oida
, p. 2241 - 2246 (2007/10/02)
Stereocontrolled synthesis of an optically active triazolylmethyloxirane 2, an important intermediate for the preparation of antifungal oxazolidine compounds 1, was achieved by two methods using L-lactic acid as a starting material. The key intermediate ketone 6 used in the procedures also served for the synthesis of the enantiomer of 2 and the corresponding diastereomeric epoxide.
Triazole derivatives, their preparation and their use as fungicides
-
, (2008/06/13)
Compounds of formula (I): in which: Ar is optionally substituted phenyl; R1 is hydrogen or alkyl; X is optionally unsaturated alkylene, cycloalkylene or both; mis 0 or 1; -Yn-R2 is azido, phthalimido, 1-oxo-2,3-dihydro-2-isoindolyl, protected hydroxy or -OSO2R4 (in which R4 is alkyl group, haloalkyl or optionally substituted phenyl); or Y represents a group of formula -N(R5)CO-, -N(R5)CO-CH=CH-, -O-CO-, -O-CO-CH=CH-, -S-CO- or -S-CO-CH=CH- (in which R5 is hydrogen or alkyl); nis 0 or 1; R2 is alkyl, haloalkyl or optionally substituted phenyl, naphthyl or heterocyclic; and R3 is hydrogen; or R3 and -Xm-Yn-R2 together are a group of formula (II): in which R2 is as defined above, pis 0 or 1, and qis 0 or 1;, and acid addition salts thereof are fungicides, which find considerable value in the eradication of fungi in both agriculture and medicine.
