3-[(4-amino-5-chloro-2-hydroxyphenyl)methyl]-5-[3,4-dichlorophenyl]-1,3,4-oxadiazol-2-(3H)-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[(4-amino-5-chloro-2-hydroxyphenyl)methyl]-5-[3,4-dichlorophenyl]-1,3,4-oxadiazol-2-(3H)-one
• 英文别名: 3-[(4-Amino-5-chloro-2-hydroxyphenyl)methyl]-5-(3,4-dichlorophenyl)-1,3,4-oxadiazol-2-one
• 化学式: C₁₅H₁₀Cl₃N₃O₃
• 分子量: 386.622
• InChiKey: JBUNVWOOAFSLGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  88.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-[(4-amino-5-chloro-2-methoxyphenyl)methyl]-5-[3,4-dichlorophenyl]-1,3,4-oxadiazol-2-(3H)-one 以 四氢呋喃 、 二氯甲烷 为溶剂， 以853 mg (97%)的产率得到3-[(4-amino-5-chloro-2-hydroxyphenyl)methyl]-5-[3,4-dichlorophenyl]-1,3,4-oxadiazol-2-(3H)-one
  参考文献：
  名称：

  Diphenyl oxadiazolones as potassium channel modulators

  摘要：

  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。

  公开号：

  US05869509A1

文献信息

• 3-[(5-Chloro-2-hydroxyphenyl)methyl]-5-[4-(trifluoromethyl)phenyl ]-1,3,4-oxadiazol-2(3<i>H</i>)-one, BMS-191011:  Opener of Large-Conductance Ca²⁺-Activated Potassium (Maxi-K) Channels, Identification, Solubility, and SAR
  作者：Jeffrey L. Romine、Scott W. Martin、Nicholas A. Meanwell、Valentin K. Gribkoff、Christopher G. Boissard、Steven I. Dworetzky、Joanne Natale、Sandra Moon、Astrid Ortiz、Swamy Yeleswaram、Lorraine Pajor、Qi Gao、John E. Starrett

  DOI：10.1021/jm061006n

  日期：2007.2.8

  Compound 8a (BMS-191011), an opener of the cloned large-conductance, Ca2+-activated potassium (maxi-K) channel, demonstrated efficacy in in vivo stroke models, which led to its nomination as a candidate for clinical evaluation. Its maxi-K channel opening properties were consistent with its structural topology, being derived by combining elements from other known maxi-K openers. However, 8a suffered from poor aqueous solubility, which complicated elucidation of SAR during in vitro evaluation. The activity of 8a in in vivo stroke models and studies directed toward improving its solubility are reported herein. Enhanced solubility was achieved by appending heterocycles to the 8a scaffold, and a notable observation was made that inclusion of a simple amino group (anilines 8k and 8l) yielded excellent in vitro maxi-K ion channel opening activity and enhanced brain-to-plasma partitioning compared to the appended heterocycles.
• DRUG FOR TREATING TINNITUS
  申请人：UNIVERSITY OF SOUTH FLORIDA

  公开号：US20210393596A1

  公开（公告）日：2021-12-23

  Compounds, pharmaceutical compositions, and methods for treating tinnitus in a subject in need thereof. The methods include administering a therapeutically effective amount of a compound having a structure represented by Formula I as described herein. The compounds and compositions are administered transdermally or orally, preferably via a sustained release mechanism. The compounds and compositions reduce at least one behavioral correlate of tinnitus and/or at least one neurophysiological correlate of tinnitus. The compounds and compositions reduce hyperactivity in the auditory system.
• US5869509A
  申请人：——

  公开号：US5869509A

  公开（公告）日：1999-02-09
• US6077861A
  申请人：——

  公开号：US6077861A

  公开（公告）日：2000-06-20
• US6271249B1
  申请人：——

  公开号：US6271249B1

  公开（公告）日：2001-08-07