2-氯-1-(6-甲基-1H-吲哚-3-基)乙酮 | 115027-18-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 2-氯-1-(6-甲基-1H-吲哚-3-基)乙酮
• 英文名称: 6-methyl-3-(α-chloroacetyl)indole
• 英文别名: 2-chloro-1-(6-methyl-1H-indol-3-yl)ethanone
• CAS: 115027-18-4
• 化学式: C₁₁H₁₀ClNO
• mdl: MFCD03848185
• 分子量: 207.659
• InChiKey: XVEKDVUZMSRMAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-氯-1-(6-甲基-1H-吲哚-3-基)乙酮 、 1-(N-benzylguanyl)thiourea 以 乙醇 为溶剂， 生成 N-Benzyl-N'-[4-(6-methyl-1H-indol-3-yl)-thiazol-2-yl]-guanidine
  参考文献：
  名称：

  Antiulcer agents. 4-Substituted 2-guanidinothiazoles: reversible, competitive, and selective inhibitors of gastric H+,K+-ATPase

  摘要：

  A series of 4-substituted 2-guanidinothiazoles has been found to inhibit the gastric proton-pump enzyme H+,K(+)-ATPase. In general, these compounds were reversible inhibitors of canine gastric H+,K(+)-ATPase, competitive at the K+ site, and selective relative to canine renal Na+,K(+)-ATPase. Structure-activity relationship (SAR) studies on this series revealed no general replacement for the guanidinothiazole. On the other hand, use of pyrrolyl, phenyl, and indolyl groups as the C-4 substituent yielded active compounds. Extensive studies of substitution patterns on these 4-aryl groups led to more active compounds, but no consistent SAR became apparent. Monosubstitution of the guanidine and substitution of the thiazole at C-5 both often led to increased activity, but combining these changes generated compounds less active than the parents. Despite 100-fold improvement in in vitro inhibitory potency, only a 3-fold increase in gastric antisecretory activity in rats was observed for these agents.

  DOI：

  10.1021/jm00164a012
• 作为产物：
  描述：

  6-甲基吲哚 、 氯乙酰氯 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以56%的产率得到2-氯-1-(6-甲基-1H-吲哚-3-基)乙酮
  参考文献：
  名称：

  4-(吲哚-3-基)噻唑-2-胺和4-吲哚-3-基)噻唑酰胺作为新型抗微生物剂。合成、计算机模拟和体外评估

  摘要：

  本手稿涉及 29 种 4-（吲哚-3-基）噻唑-2-胺和 4-吲哚-3-基）噻唑酰胺的抗菌活性的合成、计算和实验评估。对革兰氏 (+) 和革兰氏 (-) 细菌的抗菌活性评估表明，吲哚衍生物的 MIC 范围为 0.06-1.88 mg/mL，而在 14 种甲基吲哚衍生物中，只有 6 种具有活性，MIC 为范围为 0.47–1.88 mg/mL。S. aureus似乎是最具抗性的菌株，而S. Typhimurium 是最敏感的。化合物5x是最有希望的，MIC 在 0.06–0.12 mg/mL 范围内，其次是5d和5m. 对耐药菌株，即MRSA这三种化合物的评价P. 铜绿假单胞菌和E. 大肠杆菌，表明，它们更有效的抗MRSA比氨苄青霉素。此外，与氨苄青霉素和链霉素相比，化合物5m和5x是生物膜形成的优良抑制剂，就化合物5d、5m和5x以加性方式与链霉素相互作用而言。一些化合物的抗真菌活性超过或

  DOI：

  10.3390/ph14111096

文献信息

• Antiulcer agents. 4-Substituted 2-guanidinothiazoles: reversible, competitive, and selective inhibitors of gastric H+,K+-ATPase
  作者：John L. LaMattina、Peter A. McCarthy、Lawrence A. Reiter、William F. Holt、Li An Yeh

  DOI：10.1021/jm00164a012

  日期：1990.2

  A series of 4-substituted 2-guanidinothiazoles has been found to inhibit the gastric proton-pump enzyme H+,K(+)-ATPase. In general, these compounds were reversible inhibitors of canine gastric H+,K(+)-ATPase, competitive at the K+ site, and selective relative to canine renal Na+,K(+)-ATPase. Structure-activity relationship (SAR) studies on this series revealed no general replacement for the guanidinothiazole. On the other hand, use of pyrrolyl, phenyl, and indolyl groups as the C-4 substituent yielded active compounds. Extensive studies of substitution patterns on these 4-aryl groups led to more active compounds, but no consistent SAR became apparent. Monosubstitution of the guanidine and substitution of the thiazole at C-5 both often led to increased activity, but combining these changes generated compounds less active than the parents. Despite 100-fold improvement in in vitro inhibitory potency, only a 3-fold increase in gastric antisecretory activity in rats was observed for these agents.
• 4-(Indol-3-yl)thiazole-2-amines and 4-ιndol-3-yl)thiazole Acylamines as Νovel Antimicrobial Agents: Synthesis, In Silico and In Vitro Evaluation
  作者：Sergei Simakov、Victor Kartsev、Anthi Petrou、Ioannis Nicolaou、Athina Geronikaki、Marija Ivanov、Marina Kostic、Jasmina Glamočlija、Marina Soković、Despoina Talea、Ioannis S. Vizirianakis

  DOI：10.3390/ph14111096

  日期：——

  4-ιndol-3-yl)thiazole acylamines. An evaluation of antibacterial activity against Gram (+) and Gram (−) bacteria revealed that the MIC of indole derivatives is in the range of 0.06–1.88 mg/mL, while among fourteen methylindole derivatives, only six were active, with an MIC in the range of of 0.47–1.88 mg/mL. S. aureus appeared to be the most resistant strain, while S. Typhimurium was the most sensitive

  本手稿涉及 29 种 4-（吲哚-3-基）噻唑-2-胺和 4-吲哚-3-基）噻唑酰胺的抗菌活性的合成、计算和实验评估。对革兰氏 (+) 和革兰氏 (-) 细菌的抗菌活性评估表明，吲哚衍生物的 MIC 范围为 0.06-1.88 mg/mL，而在 14 种甲基吲哚衍生物中，只有 6 种具有活性，MIC 为范围为 0.47–1.88 mg/mL。S. aureus似乎是最具抗性的菌株，而S. Typhimurium 是最敏感的。化合物5x是最有希望的，MIC 在 0.06–0.12 mg/mL 范围内，其次是5d和5m. 对耐药菌株，即MRSA这三种化合物的评价P. 铜绿假单胞菌和E. 大肠杆菌，表明，它们更有效的抗MRSA比氨苄青霉素。此外，与氨苄青霉素和链霉素相比，化合物5m和5x是生物膜形成的优良抑制剂，就化合物5d、5m和5x以加性方式与链霉素相互作用而言。一些化合物的抗真菌活性超过或