5-chloro-7-methyl-2-(1-piperazinyl)benzoxazole | 270917-30-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 5-chloro-7-methyl-2-(1-piperazinyl)benzoxazole
• 英文别名: 5-chloro-7-methyl-2-piperazin-1-yl-1,3-benzoxazole
• CAS: 270917-30-1
• 化学式: C₁₂H₁₄ClN₃O
• 分子量: 251.716
• InChiKey: MZUBRHZGTLTPRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 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-piperazinyl)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-piperazinyl)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：

  4-氯-2-甲基-6-硝基苯酚 在 sulfide carbon 、 铂 氢氧化钾 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 、 甲苯 为溶剂， 反应 48.0h， 生成 5-chloro-7-methyl-2-(1-piperazinyl)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

• 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
• US7045516B1
  申请人：——

  公开号：US7045516B1

  公开（公告）日：2006-05-16
• Synthesis of new carbon-11 labeled benzoxazole derivatives for PET imaging of 5-HT3 receptor
  作者：Mingzhang Gao、Min Wang、Gary D. Hutchins、Qi-Huang Zheng

  DOI：10.1016/j.ejmech.2007.10.017

  日期：2008.7

  in brain, heart and cancer diseases, and imaging agents for use in biomedical imaging technique PET. Benzoxazole derivatives are a novel class of 5-HT(3) receptor partial agonists with high binding affinity. Carbon-11 labeled benzoxazole derivatives have been synthesized as new potential PET radioligands for imaging 5-HT(3) receptor. The target tracers were prepared by N-[(11)C]methylation of their

  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％，
• Orally Active Benzoxazole Derivative as 5-HT₃ Receptor Partial Agonist for Treatment of Diarrhea-Predominant Irritable Bowel Syndrome
  作者：Satoshi Yoshida、Sojiro Shiokawa、Ken-ichi Kawano、Tomoko Ito、Hiroshi Murakami、Hisashi Suzuki、Yasuo Sato

  DOI：10.1021/jm050209t

  日期：2005.11.1

  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.