4-Chloro-2,3-dimethyl-6-nitrophenol | 211363-27-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-Chloro-2,3-dimethyl-6-nitrophenol
• CAS: 211363-27-8
• 化学式: C₈H₈ClNO₃
• 分子量: 201.609
• InChiKey: CFRHQFGPONDFPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Chloro-2,3-dimethyl-6-nitrophenol 在 sulfide carbon 、 铂 氢氧化钾 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 32.0h， 生成 5-chloro-2-mercapto-6,7-dimethylbenzoxazole
  参考文献：
  名称：

  Benzoxazole Derivatives as Novel 5-HT₃ Receptor Partial Agonists in the Gut

  摘要：

  A series of benzoxazoles with a nitrogen-containing heterocyclic substituent at the 2-position was prepared and evaluated for 5-HT3 partial agonist activity on isolated guinea pig ileum. The nature of the substituent at the 5-position of the benzoxazole ring affected the potency for the 5-HT3 receptor, and the 5-chloro derivatives showed increased potency and lowered intrinsic activity. 5-Chloro-7-methyl-2-(4-methyl-1-homopiperazinyl)benzoxazole (6v) exhibited a high binding affinity in the same range as that of the 5-HT3 antagonist granisetron, and its intrinsic activity was 12% of that of 5-HT. Compound 6v inhibited 5-HT-evoked diarrhea but did not prolong the transition time of glass beads in the normal distal colon even at a dose of 100 times the ED50 for diarrhea inhibition in mice. Compounds of this type are expected to be effective for the treatment of irritable bowel syndrome without the side effect of constipation.

  DOI：

  10.1021/jm9801004
• 作为产物：
  描述：

  二甲酚 在 磺酰氯 、 硫酸 、 硝酸 、 溶剂黄146 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 4-Chloro-2,3-dimethyl-6-nitrophenol
  参考文献：
  名称：

  Benzoxazole Derivatives as Novel 5-HT₃ Receptor Partial Agonists in the Gut

  摘要：

  A series of benzoxazoles with a nitrogen-containing heterocyclic substituent at the 2-position was prepared and evaluated for 5-HT3 partial agonist activity on isolated guinea pig ileum. The nature of the substituent at the 5-position of the benzoxazole ring affected the potency for the 5-HT3 receptor, and the 5-chloro derivatives showed increased potency and lowered intrinsic activity. 5-Chloro-7-methyl-2-(4-methyl-1-homopiperazinyl)benzoxazole (6v) exhibited a high binding affinity in the same range as that of the 5-HT3 antagonist granisetron, and its intrinsic activity was 12% of that of 5-HT. Compound 6v inhibited 5-HT-evoked diarrhea but did not prolong the transition time of glass beads in the normal distal colon even at a dose of 100 times the ED50 for diarrhea inhibition in mice. Compounds of this type are expected to be effective for the treatment of irritable bowel syndrome without the side effect of constipation.

  DOI：

  10.1021/jm9801004

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
• Benzoxazole Derivatives as Novel 5-HT₃ Receptor Partial Agonists in the Gut
  作者：Yasuo Sato、Megumi Yamada、Satoshi Yoshida、Tomoko Soneda、Midori Ishikawa、Tetsutaro Nizato、Kokichi Suzuki、Fukio Konno

  DOI：10.1021/jm9801004

  日期：1998.7.1

  A series of benzoxazoles with a nitrogen-containing heterocyclic substituent at the 2-position was prepared and evaluated for 5-HT3 partial agonist activity on isolated guinea pig ileum. The nature of the substituent at the 5-position of the benzoxazole ring affected the potency for the 5-HT3 receptor, and the 5-chloro derivatives showed increased potency and lowered intrinsic activity. 5-Chloro-7-methyl-2-(4-methyl-1-homopiperazinyl)benzoxazole (6v) exhibited a high binding affinity in the same range as that of the 5-HT3 antagonist granisetron, and its intrinsic activity was 12% of that of 5-HT. Compound 6v inhibited 5-HT-evoked diarrhea but did not prolong the transition time of glass beads in the normal distal colon even at a dose of 100 times the ED50 for diarrhea inhibition in mice. Compounds of this type are expected to be effective for the treatment of irritable bowel syndrome without the side effect of constipation.