6-{(4-chlorophenyl)(1H-1,2,4-triazol-1-yl)methyl}-1H-benzo[d][1,2,3]triazole | 247153-23-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 6-{(4-chlorophenyl)(1H-1,2,4-triazol-1-yl)methyl}-1H-benzo[d][1,2,3]triazole
• 英文别名: 5-[(4-chlorophenyl)-(1,2,4-triazol-1-yl)methyl]-2H-benzotriazole
• CAS: 247153-23-7
• 化学式: C₁₅H₁₁ClN₆
• 分子量: 310.746
• InChiKey: YXPXNFVPOUKWKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  72.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-{(4-chlorophenyl)(1H-1,2,4-triazol-1-yl)methyl}-1H-benzo[d][1,2,3]triazole 在 CHIRALPAK AD-H column 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 (R)-6-((4-chlorophenyl)(1H-1,2,4-triazol-1-yl)methyl)-1H-benzo[d][1,2,3]-triazole 、 (S)-6-((4-chlorophenyl)(1H-1,2,4-triazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole
  参考文献：
  名称：

  Practical synthesis of precursor of [N-methyl-11C]vorozole, an efficient PET tracer targeting aromatase in the brain

  摘要：

  A practical method to prepare precursor of [N-methyl-C-11]vorozole ([C-11]vorozole), an efficient positron emission tomography (PET) tracer for imaging aromatase in the living body, was established. Sufficient amount of the racemate including norvorozole, a demethylated vorozole derivative used as a precursor of [C-11]vorozole, became available by means of high-yield eight-step synthesis. The enantiomers were separated by preparative HPLC using a chiral stationary phase column to give optically pure norvorozole and its enantiomer. From the latter, ent-[C-11]vorozole, an enantiomer of [C-11]vorozole, was prepared and used in the PET study for the first time, which was shown to bind very weakly to aromatase in rhesus monkey brain supporting the previous pharmacological results. The stable supply of norvorozole will facilitate further researches on aromatase in the living body including brain by the PET technique. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.057
• 作为产物：
  描述：

  (4-氯-3-硝基苯基)-(4-氯苯基)-甲酮 在 盐酸 、 sodium tetrahydroborate 、 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 甲基磺酰氯 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 6-{(4-chlorophenyl)(1H-1,2,4-triazol-1-yl)methyl}-1H-benzo[d][1,2,3]triazole
  参考文献：
  名称：

  Practical synthesis of precursor of [N-methyl-11C]vorozole, an efficient PET tracer targeting aromatase in the brain

  摘要：

  A practical method to prepare precursor of [N-methyl-C-11]vorozole ([C-11]vorozole), an efficient positron emission tomography (PET) tracer for imaging aromatase in the living body, was established. Sufficient amount of the racemate including norvorozole, a demethylated vorozole derivative used as a precursor of [C-11]vorozole, became available by means of high-yield eight-step synthesis. The enantiomers were separated by preparative HPLC using a chiral stationary phase column to give optically pure norvorozole and its enantiomer. From the latter, ent-[C-11]vorozole, an enantiomer of [C-11]vorozole, was prepared and used in the PET study for the first time, which was shown to bind very weakly to aromatase in rhesus monkey brain supporting the previous pharmacological results. The stable supply of norvorozole will facilitate further researches on aromatase in the living body including brain by the PET technique. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.057

文献信息

• PROCESS FOR PREPARING ENANTIOMERICALLY PURE 6- (4-CHLOROPHENYL)(1H --TRIAZOL-1,2,4-TRIAZOL-1-YL)METHYL]-1-METHYL-1H --BENZOTRIAZOLE
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP0668861A1

  公开（公告）日：1995-08-30
• Radio-methyl Vorozole and Methods for Making and Using the Same
  申请人：Kim Sung Won

  公开号：US20100209344A1

  公开（公告）日：2010-08-19

  Radiotracer vorozole compounds for in vivo and in vitro assaying, studying and imaging cytochrome P450 aromatase enzymes in humans, animals, and tissues and methods for making and using the same are provided. [N-radio-methyl] vorozole substantially separated from an N-3 radio-methyl isomer of vorozole is provided. Separation is accomplished through use of chromatography resins providing multiple mechanisms of selectivity.
• US8795629B2
  申请人：——

  公开号：US8795629B2

  公开（公告）日：2014-08-05
• US8802053B2
  申请人：——

  公开号：US8802053B2

  公开（公告）日：2014-08-12
• Practical synthesis of precursor of [N-methyl-11C]vorozole, an efficient PET tracer targeting aromatase in the brain
  作者：Kayo Takahashi、Gen Yamagishi、Toshiyuki Hiramatsu、Ayako Hosoya、Kayo Onoe、Hisashi Doi、Hiroko Nagata、Yasuhiro Wada、Hirotaka Onoe、Yasuyoshi Watanabe、Takamitsu Hosoya

  DOI：10.1016/j.bmc.2010.12.057

  日期：2011.2

  A practical method to prepare precursor of [N-methyl-C-11]vorozole ([C-11]vorozole), an efficient positron emission tomography (PET) tracer for imaging aromatase in the living body, was established. Sufficient amount of the racemate including norvorozole, a demethylated vorozole derivative used as a precursor of [C-11]vorozole, became available by means of high-yield eight-step synthesis. The enantiomers were separated by preparative HPLC using a chiral stationary phase column to give optically pure norvorozole and its enantiomer. From the latter, ent-[C-11]vorozole, an enantiomer of [C-11]vorozole, was prepared and used in the PET study for the first time, which was shown to bind very weakly to aromatase in rhesus monkey brain supporting the previous pharmacological results. The stable supply of norvorozole will facilitate further researches on aromatase in the living body including brain by the PET technique. (C) 2010 Elsevier Ltd. All rights reserved.