2-氯-1-(5-甲基-1H-吲哚-3-基)乙-1-酮 | 38693-12-8

• 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-(5-甲基-1H-吲哚-3-基)乙-1-酮
• 英文名称: 2-chloro-1-(5-methyl-1H-indol-3-yl)ethanone
• 英文别名: 5-Methyl-3-chloracetyl-indol
• CAS: 38693-12-8
• 化学式: C₁₁H₁₀ClNO
• mdl: MFCD06589825
• 分子量: 207.659
• InChiKey: JYKPHNPNYVGFFG-UHFFFAOYSA-N

物化性质

• 沸点：
  389.3±27.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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

反应信息

• 作为反应物：
  描述：

  2-氯-1-(5-甲基-1H-吲哚-3-基)乙-1-酮 、 1-(N-benzylguanyl)thiourea 以 乙醇 为溶剂， 生成 N-Benzyl-N'-[4-(5-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：

  5-甲基吲哚 以 四氢呋喃 、 正己烷 为溶剂， 反应 25.0h， 生成 2-氯-1-(5-甲基-1H-吲哚-3-基)乙-1-酮
  参考文献：
  名称：

  通过常见的N-吲哚基三乙基硼酸酯从游离（NH）吲哚中集体合成3-乙酰基吲哚，吲哚-3-羧酸酯，吲哚-3-亚磺酸和3-（甲基磺酰基）吲哚

  摘要：

  据报道，通过常见的N-吲哚基三乙基硼酸酯中间体，可以利用容易获得的亲电子试剂（如酰氯，氯甲酸酯，亚硫酰氯和甲基磺酰氯）对游离（NH）吲哚进行一般和直接的C3功能化。反应在温和条件下平稳进行，收率高达93％。在C2，C4，C5，C6和C7位置带有取代基的吲哚具有良好的耐受性。各种重要的3-acylindoles，吲哚-3-羧酸酯，吲哚-3-亚磺酸和3-（甲基磺酰基）吲哚的易于获得证明了该方法的高度相容性和实用性。

  DOI：

  10.1021/acs.orglett.6b01970

文献信息

• Sepiapterin Reductase Inhibitors For The Treatment of Pain
  申请人：Blagg Julian

  公开号：US20120322800A1

  公开（公告）日：2012-12-20

  Disclosed herein are small molecule heterocyclic inhibitors of sepiapterin reductase (SPR), and prodrugs and pharmaceutically acceptable salts thereof. The Also featured are pharmaceutical compositions of the compounds and uses of these compounds for the treatment or prevention of pain (e.g., inflammatory pain, nociceptive pain, functional pain, and neuropathic pain).
• SEPIAPTERIN REDUCTASE INHIBITORS FOR THE TREATMENT OF PAIN
  申请人：Children's Medical Center Corporation

  公开号：US20160031812A1

  公开（公告）日：2016-02-04

  Disclosed herein are small molecule heterocyclic inhibitors of sepiapterin reductase (SPR), and prodrugs and pharmaceutically acceptable salts thereof. The Also featured are pharmaceutical compositions of the compounds and uses of these compounds for the treatment or prevention of pain (e.g., inflammatory pain, nociceptive pain, functional pain, and neuropathic pain).
• US9169234B2
  申请人：——

  公开号：US9169234B2

  公开（公告）日：2015-10-27
• 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.
• Collective Synthesis of 3-Acylindoles, Indole-3-carboxylic Esters, Indole-3-sulfinic Acids, and 3-(Methylsulfonyl)indoles from Free (N–H) Indoles via Common <i>N</i>-Indolyl Triethylborate
  作者：Zhi-Wei Zhang、Hong Xue、Hailing Li、Huaiping Kang、Juan Feng、Aijun Lin、Shouxin Liu

  DOI：10.1021/acs.orglett.6b01970

  日期：2016.8.5

  A general and direct C3 functionalization of free (N–H) indoles with readily available electrophiles such as acid chlorides, chloroformates, thionyl chloride, and methylsulfonyl chloride via a common N-indolyl triethylborate intermediate is reported. The reaction proceeds smoothly under mild conditions in up to 93% yield. Indoles with substituents at the C2, C4, C5, C6, and C7 positions are well tolerated

  据报道，通过常见的N-吲哚基三乙基硼酸酯中间体，可以利用容易获得的亲电子试剂（如酰氯，氯甲酸酯，亚硫酰氯和甲基磺酰氯）对游离（NH）吲哚进行一般和直接的C3功能化。反应在温和条件下平稳进行，收率高达93％。在C2，C4，C5，C6和C7位置带有取代基的吲哚具有良好的耐受性。各种重要的3-acylindoles，吲哚-3-羧酸酯，吲哚-3-亚磺酸和3-（甲基磺酰基）吲哚的易于获得证明了该方法的高度相容性和实用性。