1-(6-hydroxynaphthalen-2-yl)-1-(1-trityl-1H-imidazol-4-yl)-2-methyl-1-propanol | 247173-85-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-(6-hydroxynaphthalen-2-yl)-1-(1-trityl-1H-imidazol-4-yl)-2-methyl-1-propanol
• 英文别名: 6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-naphthol；6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthol；6-[1-hydroxy-2-methyl-1-(1-tritylimidazol-4-yl)propyl]naphthalen-2-ol
• CAS: 247173-85-9
• 化学式: C₃₆H₃₂N₂O₂
• 分子量: 524.662
• InChiKey: WPIBZYGORDPFJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  58.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(6-hydroxynaphthalen-2-yl)-1-(1-trityl-1H-imidazol-4-yl)-2-methyl-1-propanol 在 trifluoromethanesulfonic acid anhydride 作用下， 以 吡啶 为溶剂， 生成 6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-naphthyl trifluoromethanesulfonate
  参考文献：
  名称：

  Imidazol-4-ylmehanols and their use as inhibitors of steroid C17-20 lyase

  摘要：

  Imidazol-4-ylmethanols及其用于预防和治疗原发性肿瘤、肿瘤转移和复发、伴随肿瘤的各种症状、前列腺肥大、男性化、多毛症、男性型脱发、性早熟、子宫内膜异位症、子宫肌瘤、乳腺病和多囊卵巢综合征的用途被披露。

  公开号：

  US06649643B1
• 作为产物：
  描述：

  (6-溴萘-2-基氧基)-叔丁基二甲基硅烷 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.16h， 生成 1-(6-hydroxynaphthalen-2-yl)-1-(1-trityl-1H-imidazol-4-yl)-2-methyl-1-propanol
  参考文献：
  名称：

  17,20-Lyase inhibitors. Part 4: Design, synthesis and structure–activity relationships of naphthylmethylimidazole derivatives as novel 17,20-lyase inhibitors

  摘要：

  A novel series of naphthylmethylimidazole derivatives and related compounds have been investigated as selective 17,20-lyase inhibitors. Optimization of the substituent at the 6-position on the naphthalene ring was performed to yield a methylcarbamoyl derivative, which exhibited potent inhibitory activity against human 17,20-lyase and promising selectivity (> 200-fold) for 17,20-lyase over CYP3A4. Further modifications of the methylcarbamoyl derivative led to the discovery of the corresponding tricyclic compound, which showed highly potent activity against human 17,20-lyase (IC50 19 nM) and good selectivity (> 1000-fold) for inhibition of 17,20-lyase over CYP3A4. Additional biological evaluation revealed that the tricyclic compound had potent in vivo efficacy in monkeys and favorable pharmacokinetic profiles when administered in rats. Asymmetric synthesis of the selective tricyclic inhibitor was also achieved using a chiral alpha-hydroxy ketone. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.017

文献信息

• Naphthalene derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06573289B1

  公开（公告）日：2003-06-03

  A composition containing a compound of the formula: wherein A is a nitrogen-containing heterocyclic group which may be substituted, R1 is a hydrogen atom, hydrocarbon group which may be substituted, or monocyclic aromatic heterocyclic group which may be substituted, R2 is a hydrogen atom or a lower alkyl group which may be substituted, R3, R4, R5, R6, R7, R8 and R9 are independently a hydrogen atom, a hydrocarbon group which may be substituted, a hydroxy group which may be substituted, a thiol group which may be substituted, an amino group which may be substituted, an acyl group or a halogen atom, a salt thereof or a prodrug thereof has steroid C17,20-lyase inhibitory activity, and is useful for preventing and treating for example, primary cancer of malignant tumor, its metastasis and recurrence thereof.

  包含以下公式化合物的组合物： 其中A是可被取代的含氮杂环基团，R1是氢原子、可被取代的烃基团或可被取代的单环芳族杂环基团，R2是氢原子或可被取代的低级烷基团，R3、R4、R5、R6、R7、R8和R9独立地是氢原子、可被取代的烃基团、可被取代的羟基、可被取代的硫醇基、可被取代的氨基、酰基或卤素原子，其盐或前药对类固醇C17,20-裂解酶具有抑制作用，并且对于例如预防治疗原发恶性肿瘤、其转移和复发等是有用的。
• Imidazole derivatives, process for their preparation and their use
  申请人：——

  公开号：US20040024039A1

  公开（公告）日：2004-02-05

  The present invention provides a compound having a steroid C 17,20 -lyase inhibitory activity, which is useful as a prophylactic or therapeutic agent of prostatism and tumor such as breast cancer and the like. A compound represented by the formula: 1 wherein R is a hydrogen atom or a protecting group, R 1 is a lower alkyl group or a cyclic alkyl group, and ring A and ring B are each an optionally substituted 5-membered or 6-membered ring having an amide bond in the ring, or a salt thereof.

  本发明提供了一种具有类固醇C17,20-裂解酶抑制活性的化合物，该化合物可用作前列腺增生和乳腺癌等肿瘤的预防或治疗剂。该化合物由以下式表示：1其中R是氢原子或保护基，R1是较低的烷基或环烷基，环A和环B分别是具有环中酰胺键的可选取代的5-或6-成员环，或其盐。
• IMIDAZOLE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR USE
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1344777B1

  公开（公告）日：2011-03-16
• NAPHTHALENE DERIVATIVES, THEIR PRODUCTION AND USE
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1073640B1

  公开（公告）日：2005-04-13
• IMIDAZOL-4-YLMETHANOLS USED AS INHIBITORS OF STEROID C17-20 LYASE
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1222174B1

  公开（公告）日：2009-05-27