5-chloro-7-methyl-2-(1-homopiperazinyl)benzoxazole | 270917-08-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 5-chloro-7-methyl-2-(1-homopiperazinyl)benzoxazole
• 英文别名: 5-chloro-2-(1-homopiperazinyl)-7-methylbenzooxazole；5-chloro-2-(1-homopiperazinyl)-7-methylbenzoxazole；5-Chloro-2-(1,4)diazepan-1-yl-7-methyl-benzooxazole；5-chloro-2-(1,4-diazepan-1-yl)-7-methyl-1,3-benzoxazole
• CAS: 270917-08-3
• 化学式: C₁₃H₁₆ClN₃O
• 分子量: 265.743
• InChiKey: QPKABSXJDCZNKQ-UHFFFAOYSA-N

物化性质

• 熔点：
  68-70 °C(Solv: acetonitrile (75-05-8))
• 沸点：
  409.0±55.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  41.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-chloro-7-methyl-2-(1-homopiperazinyl)benzoxazole 、 [11C]methyl triflate 在 sodium hydroxide 作用下， 以 乙腈 为溶剂， 生成 5-chloro-7-methyl-2-(4-[11C]methyl-1-homopiperazinyl)benzoxazole
  参考文献：
  名称：

  合成新的碳11标记的5-HT（3）受体PET成像的苯并恶唑衍生物。

  摘要：

  5-HT（3）受体是开发用于脑，心脏病和癌症疾病的治疗剂以及用于生物医学成像技术PET的成像剂的有吸引力的靶标。苯并恶唑衍生物是一类新型的具有高结合亲和力的5-HT（3）受体部分激动剂。碳11标记的苯并恶唑衍生物已被合成为用于成像5-HT（3）受体的新的潜在PET放射性配体。目标示踪剂是通过使用[（11）C] CH（3）OTf通过其相应前体的N-[（11）C]甲基化制备的，并通过HPLC纯化程序以40-50％的放射化学收率分离，将其衰减校正为基于[（11）C] CO（2）的轰炸（EOB）结束。从EOB开始，总的合成时间为20-25分钟。放射化学纯度> 99％，

  DOI：

  10.1016/j.ejmech.2007.10.017
• 作为产物：
  描述：

  2-氨基-4-氯-6-甲基苯酚 在 氢氧化钾 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 24.0h， 生成 5-chloro-7-methyl-2-(1-homopiperazinyl)benzoxazole
  参考文献：
  名称：

  Orally Active Benzoxazole Derivative as 5-HT₃ Receptor Partial Agonist for Treatment of Diarrhea-Predominant Irritable Bowel Syndrome

  摘要：

  During our search for therapeutic agents to treat diarrhea-predominant IBS, we found that 2-substituted benzoxazole derivatives have a characteristic 5-HT3 receptor partial agonist activity with high affinity. Some of these compounds showed high in vitro metabolical. stability, and 6g showed marked antidiarrhetic activity with little side effect of constipation in in vivo tests. Our results indicate that 5-HT3 receptor partial agonists might be superior as therapeutic agents to the drugs currently used for IBS treatment.

  DOI：

  10.1021/jm050209t

文献信息

• [EN] SYNTHESIS OF 2-AMINOBENZOXAZOLE COMPOUNDS<br/>[FR] SYNTHÈSE DE COMPOSÉS DE 2-AMINO-BENZOXAZOLE
  申请人：ALBANY MOLECULAR RES INC

  公开号：WO2010048514A1

  公开（公告）日：2010-04-29

  A method for forming an optionally substituted 2-aminobenzoxazole compound includes: contacting an optionally substituted 2-aminophenol compound with (1) an amine of the formula NHR2R3, wherein R2 and R3 are each independently selected from H, an optionally substituted alkyl group or an optionally substituted aryl group, or R2 and R3, taken together with the nitrogen atom to which they are attached, form an optionally substituted heterocyclic ring; and (2) a reactant selected from the group consisting of: (a) C(OR)4, wherein R represents an alkyl group; (b) C(OAr)4, wherein Ar represents an aryl group; and (c) CCl2(OAr)2, wherein Ar represents an aryl group, in combination with a base; thereby forming the optionally substituted 2-aminobenzoxazole compound.

  一种形成可选择取代的2-氨基苯并噁唑化合物的方法包括：将可选择取代的2-氨基苯酚化合物与（1）符合NHR2R3公式的胺接触，其中R2和R3分别独立地选自H、可选择取代的烷基或可选择取代的芳基，或者R2和R3与它们连接的氮原子一起形成可选择取代的杂环环；以及（2）选自以下组合的反应物：（a）C（OR）4，其中R代表烷基；（b）C（OAr）4，其中Ar代表芳基；和（c）CCl2（OAr）2，其中Ar代表芳基，结合碱；从而形成可选择取代的2-氨基苯并噁唑化合物。
• Serotonin 5-Ht3 Receptor Agonist
  申请人：Jikyo Tamaki

  公开号：US20070265277A1

  公开（公告）日：2007-11-15

  A serotonin 5-HT3 receptor agonist containing a compound represented by the general formula (1) [R 1 , R 3 and R 5 represent hydrogen atom, a lower alkyl group, a lower alkenyl group, a halogen atom, hydroxyl group, amino group, a lower alkoxy group, carboxyl group, carbamoyl group, or nitro group, R 2 and R 4 represent a halogen atom, hydroxyl group, or amino group, R 6 represents hydrogen atom, a lower alkyl group, or a lower alkenyl group, R 7 represents hydrogen atom, a lower alkyl group, a lower alkenyl group, or an aralkyl group, and m and n are integers of 1 to 3] or a physiologically acceptable salt thereof as an active ingredient and having both a serotonin 5-HT3 receptor antagonistic action and a serotonin 5-HT3 receptor activating action.

  含有一种化合物的5-HT3受体激动剂，该化合物由通式（1）表示 [其中R1、R3和R5代表氢原子、低碳基、低烯基、卤素原子、羟基、氨基、低烷氧基、羧基、氨基甲酰基或硝基；R2和R4代表卤素原子、羟基或氨基；R6代表氢原子、低碳基或低烯基；R7代表氢原子、低碳基、低烯基或芳基烷基；m和n为1到3的整数]或其生理上可接受的盐作为活性成分，并具有5-HT3受体拮抗作用和5-HT3受体激活作用。
• SEROTONIN 5-HT3 RECEPTOR AGONIST
  申请人：JIKYO Tamaki

  公开号：US20090118303A1

  公开（公告）日：2009-05-07

  A serotonin 5-HT3 receptor agonist containing a compound represented by the general formula (1) [R 1 , R 3 and R 5 represent hydrogen atom, a lower alkyl group, a lower alkenyl group, a halogen atom, hydroxyl group, amino group, a lower alkoxy group, carboxyl group, carbamoyl group, or nitro group, R 2 and R 4 represent a halogen atom, hydroxyl group, or amino group, R 6 represents hydrogen atom, a lower alkyl group, or a lower alkenyl group, R 7 represents hydrogen atom, a lower alkyl group, a lower alkenyl group, or an aralkyl group, and m and n are integers of 1 to 3] or a physiologically acceptable salt thereof as an active ingredient and having both a serotonin 5-HT3 receptor antagonistic action and a serotonin 5-HT3 receptor activating action.

  一种含有化合物通式（1）所代表的化合物的血清素5-HT3受体激动剂[R1、R3和R5代表氢原子、较低的烷基、较低的烯基、卤原子、羟基、氨基、较低的烷氧基、羧基、氨基甲酰基或硝基，R2和R4代表卤原子、羟基或氨基，R6代表氢原子、较低的烷基或较低的烯基，R7代表氢原子、较低的烷基、较低的烯基或芳基烷基，m和n是1到3的整数]或其生理上可接受的盐作为活性成分，具有血清素5-HT3受体拮抗作用和血清素5-HT3受体激活作用。
• Benzoxazole derivatives and drugs containing the same as the active ingredient
  申请人：Koichi Shudo

  公开号：US07045516B1

  公开（公告）日：2006-05-16

  A compound represented by the following general formula (1): wherein R1 represents a halogen atom, R2 represents hydrogen atom or a lower alkyl group, and R3 represents hydrogen atom, a lower alkyl group, a lower alkoxyl group, a hydroxy lower alkyl group, a halogen atom, or a substituted or unsubstituted amino group, wherein a substituent on the amino group is selected from the group consisting of a lower alkyl group, a lower alkenyl group, a lower alkylcarbonyl group, and an amino protective group, or a salt thereof. The compound of the present invention or a salt thereof is useful as an active ingredient of medicaments for preventive and/or therapeutic treatment of conditions of irritable bowel syndrome and digestive tract functional disorder, or condition of diarrhea.

  以下为通式（1）所代表的化合物：其中R1代表卤素原子，R2代表氢原子或较低的烷基团，R3代表氢原子、较低的烷基团、较低的烷氧基团、羟基较低的烷基团、卤素原子或取代或未取代的氨基团，氨基团上的取代基选自以下群组：较低的烷基团、较低的烯基团、较低的烷基羰基团和氨基保护基，或其盐。本发明的化合物或其盐可作为药物的活性成分，用于预防和/或治疗肠易激综合征和消化道功能障碍症状或腹泻症状。
• BENZOXAZOLE DERIVATIVES AND DRUGS CONTAINING THE SAME AS THE ACTIVE INGREDIENT
  申请人：Shudo, Koichi

  公开号：EP1134220B1

  公开（公告）日：2004-08-18