4-(5-chloro-2-methoxyphenyl)-5-[4-(trifluoromethyl)-phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-thione | 202822-51-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(5-chloro-2-methoxyphenyl)-5-[4-(trifluoromethyl)-phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-thione
• 英文别名: 4-(5-Chloro-2-methoxyphenyl)-5-[4-(trifluoromethyl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-thione；4-(5-chloro-2-methoxyphenyl)-3-[4-(trifluoromethyl)phenyl]-1H-1,2,4-triazole-5-thione
• CAS: 202822-51-3
• 化学式: C₁₆H₁₁ClF₃N₃OS
• 分子量: 385.797
• InChiKey: KDLIIFXWYVQKKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  69
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(5-chloro-2-methoxyphenyl)-5-[4-(trifluoromethyl)-phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-thione 在 吡啶盐酸盐 作用下， 反应 1.0h， 生成 4-(5-Chloro-2-hydroxyphenyl)-5-[4-(trifluoromethyl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-thione
  参考文献：
  名称：

  4,5-Diphenyltriazol-3-ones:  Openers of Large-Conductance Ca²⁺-Activated Potassium (Maxi-K) Channels

  摘要：

  A series of diphenyl-substituted heterocycles were synthesized and evaluated by electrophysiological techniques as openers of the cloned mammalian large-conductance, Call-activated potassium (maxi-K) channel. The series was designed from deannulation of known benzimidazolone maxi-K opener NS-004 (2) thereby providing an effective template for obtaining structure-activity-related information. The triazolone ring system was the most studied wherein 4,5-diphenyltriazol-3-one 6d (maxi-K = 158%) was identified as the optimal maxi-K channel opener.

  DOI：

  10.1021/jm010569q
• 作为产物：
  描述：

  5-氯-2-甲氧基苯胺 在 五氯化磷 、 三乙胺 、 肼 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 40.0h， 生成 4-(5-chloro-2-methoxyphenyl)-5-[4-(trifluoromethyl)-phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-thione
  参考文献：
  名称：

  4,5-Diphenyltriazol-3-ones:  Openers of Large-Conductance Ca²⁺-Activated Potassium (Maxi-K) Channels

  摘要：

  A series of diphenyl-substituted heterocycles were synthesized and evaluated by electrophysiological techniques as openers of the cloned mammalian large-conductance, Call-activated potassium (maxi-K) channel. The series was designed from deannulation of known benzimidazolone maxi-K opener NS-004 (2) thereby providing an effective template for obtaining structure-activity-related information. The triazolone ring system was the most studied wherein 4,5-diphenyltriazol-3-one 6d (maxi-K = 158%) was identified as the optimal maxi-K channel opener.

  DOI：

  10.1021/jm010569q

文献信息

• Diphenyl oxadiazolones as potassium channel modulators
  申请人：Bristol-Myers Squibb Company

  公开号：US05869509A1

  公开（公告）日：1999-02-09

  Novel compounds of Formula 1 are useful to treat disorders responsive to openers of the large conductance calcium-activated potassium channels: ##STR1## wherein "Het" is one of a select group of heterocyclic moieties; Z is independently for each occurrence selected from O or S; R.sup.a, R.sup.b and R.sup.c each are independently selected from hydrogen, halogen, OH, CF.sub.3, ##STR2## provided R.sup.c is not hydrogen; and when R.sup.a and R.sup.b are hydrogen, R.sup.c may be a heterocyclic moiety selected from the group consisting of imidazol-1-yl, morpholinomethyl, N-methylimidazol- 2-yl, and pyridinyl; R.sup.d and R.sup.e each are independently selected from hydrogen, halogen, CF.sub.3, NO.sub.2 or imidazol-1-yl; m, n and p each are independently selected from an integer of O or 1; and R.sup.f and R.sup.g each are independently hydrogen; C.sub.1-4 alkyl; or R.sup.f and R.sup.g, taken together with the nitrogen atom to which they are attached, is a heterocyclic moiety selected from the group consisting of N-methylpiperazine, morpholine, thiomorpholine, N-benzylpiperazine and imidazolinone.

  化合物1的新型化合物可用于治疗对大导电性钙激活钾通道开放剂反应的疾病：其中"Het"是一组特定的杂环基团之一；Z独立地为每次出现选择O或S；R.sup.a，R.sup.b和R.sup.c各自独立地选择氢，卤素，OH，CF.sub.3，provided R.sup.c不是氢；当R.sup.a和R.sup.b为氢时，R.sup.c可以是从咪唑-1-yl，morpholinomethyl，N-甲基咪唑-2-yl和吡啶基中选择的杂环基团之一；R.sup.d和R.sup.e各自独立地选择氢，卤素，CF.sub.3，NO.sub.2或咪唑-1-yl；m，n和p各自独立地选择O或1的整数；而R.sup.f和R.sup.g各自独立地选择氢；C.sub.1-4烷基；或R.sup.f和R.sup.g与它们所连接的氮原子一起选择从N-甲基哌嗪，morpholine，thiomorpholine，N-苄基哌嗪和咪唑啉酮中选择的杂环基团之一。
• Diphenyl imidazoles as potassium channel modulators
  申请人：Bristol-Myers Squibb Company

  公开号：US06271249B1

  公开（公告）日：2001-08-07

  Novel compounds of Formula 1 are useful to treat disorders responsive to openers of the large conductance calcium-activated potassium channels: wherein “Het” is one of a select group of heterocyclic moieties; Z is independently for each occurrence selected from O or S; Ra, Rb and Rc each are independently selected from hydrogen, halogen, OH, CF3, NO2, or provided Rc is not hydrogen; and when Ra and Rb are hydrogen, Rc may be a heterocyclic moiety selected from the group consisting of imidazol-1-yl, morpholinomethyl, N-methylimidazol-2-yl, and pyridin-2-yl; Rd and Re each are independently selected from hydrogen, halogen, CF3, NO2 or imidazol-1-yl; m, n and p each are independently selected from an integer of 0 or 1; and Rf and Rg each are independently hydrogen; C1-4 alkyl; or Rf and Rg, taken together with the nitrogen atom to which they are attached, is a heterocyclic moiety selected from the group consisting of N-methylpiperazine, morpholine, thiomorpholine, N-benzylpiperazine and imidazolinone.

  公式1的新化合物可用于治疗对大导电钙激活钾通道开放剂有反应的疾病：其中“Het”是一组选择性的杂环基团之一；Z是独立地对每个出现选自O或S；Ra，Rb和Rc分别独立地选自氢，卤素，OH，CF3，NO2或提供Rc不是氢；当Ra和Rb为氢时，Rc可以是从咪唑-1-基，吗啉基甲基，N-甲基咪唑-2-基和吡啶-2-基组成的杂环基团之一；Rd和Re独立地选自氢，卤素， ， 或咪唑-1-基；m，n和p各自独立地选自0或1的整数；Rf和Rg各自独立地选自氢，C1-4烷基；或者Rf和Rg与它们所连接的氮原子一起，是从N-甲基哌嗪，吗啉，硫代吗啉，N-苄基哌嗪和咪唑啉酮组成的杂环基团之一。
• DIPHENYL HETEROCYCLES AS POTASSIUM CHANNEL MODULATORS
  申请人：Bristol-Myers Squibb Company

  公开号：EP0915856A1

  公开（公告）日：1999-05-19
• EP0915856A4
  申请人：——

  公开号：EP0915856A4

  公开（公告）日：2006-04-12
• US5869509A
  申请人：——

  公开号：US5869509A

  公开（公告）日：1999-02-09