3-<(2-aminoethyl)thio>-5-chloroindole | 135381-12-3

• 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
• 英文名称: 3-<(2-aminoethyl)thio>-5-chloroindole
• 英文别名: 2-(5-chloro-3-indolylthio)-ethanamine；2-[(5-chloro-1H-indol-3-yl)sulfanyl]ethanamine
• CAS: 135381-12-3
• 化学式: C₁₀H₁₁ClN₂S
• 分子量: 226.73
• InChiKey: JNAGIIJCIXUDEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-<(2-aminoethyl)thio>-5-chloroindole 、 5-ethoxy-1-methyl-3,4-dihydro-2H-pyrrolium, tetrafluoroborate 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 N-[2-[(5-chloro-1H-indol-3-yl)sulfanyl]ethyl]-1-methylpyrrolidin-2-imine
  参考文献：
  名称：

  Cardiac-slowing amidines containing the 3-thioindole group. Potential antianginal agents

  摘要：

  A series of 3-thioindolamidines (and 3-indolamidines) related to mixidine (1) was studied for cardiac-slowing properties, following the discovery of activity for prototype thioindole 2. Structure-activity relationships were explored, leading to many potent antitachycardiac agents (6-9, 12, 13, 15-17, 20, 23, 24, 30, 34, 35, 45, and 47-49). Relative to 2, cardiac-slowing activity is enhanced by substitution of the indole nitrogen with small (C1-C3) saturated alkyl groups (6-9), unsaturated alkyl groups (12, 13, and 15-17), or a methoxyethyl group (20); replacement of the N-methyl group with alkyl (23) or phenyl groups (24); and extension of the ethylene bridge by two methylene units (34). Dethio (i.e., 3-indole) analogues of 2 with alkyl substitution on the indole nitrogen (47-49) have greater activity as well. Several potent compounds were also found to have minimal myocardial depression (6-9, 13, 45, and 47). Secondary pharmacological testing is reported for thioindoles 2, 6, 7, 9, and 28.

  DOI：

  10.1021/jm00356a021
• 作为产物：
  描述：

  5-氯吲哚 在 sodium hydroxide 、 三氟化硼四氢呋喃络合物 、 碘 、 硫脲 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 为溶剂， 反应 22.5h， 生成 3-<(2-aminoethyl)thio>-5-chloroindole
  参考文献：
  名称：

  Cardiac-slowing amidines containing the 3-thioindole group. Potential antianginal agents

  摘要：

  A series of 3-thioindolamidines (and 3-indolamidines) related to mixidine (1) was studied for cardiac-slowing properties, following the discovery of activity for prototype thioindole 2. Structure-activity relationships were explored, leading to many potent antitachycardiac agents (6-9, 12, 13, 15-17, 20, 23, 24, 30, 34, 35, 45, and 47-49). Relative to 2, cardiac-slowing activity is enhanced by substitution of the indole nitrogen with small (C1-C3) saturated alkyl groups (6-9), unsaturated alkyl groups (12, 13, and 15-17), or a methoxyethyl group (20); replacement of the N-methyl group with alkyl (23) or phenyl groups (24); and extension of the ethylene bridge by two methylene units (34). Dethio (i.e., 3-indole) analogues of 2 with alkyl substitution on the indole nitrogen (47-49) have greater activity as well. Several potent compounds were also found to have minimal myocardial depression (6-9, 13, 45, and 47). Secondary pharmacological testing is reported for thioindoles 2, 6, 7, 9, and 28.

  DOI：

  10.1021/jm00356a021

文献信息

• Aza spiro decane and use thereof in treating CNS disorders
  申请人：Novo Nordisk A/S

  公开号：US05227488A1

  公开（公告）日：1993-07-13

  Indole derivatives of formula (I) ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 may be hydrogen or lower alkyl optionally substituted by halogen; X represents oxygen or sulfur; A.sup.1 represents a straight or branched alkylene chain containing from 2 to 4 carbon atoms; R.sup.5 is hydrogen or a straight or branched alkyl group; A.sup.2 is a straight or branched, saturated or unsaturated hydrocarbon chain containing from 2 to 6 carbon atoms; and R.sup.6 is selected from a group consisting of various structures, have been found to exhibit central nervous system activities.

  式(I)的吲哚衍生物：##STR1## 其中，R.sup.1，R.sup.2，R.sup.3和R.sup.4可以是氢或低碳烷基，可选地被卤素取代；X代表氧或硫；A.sup.1代表含有2至4个碳原子的直链或支链烷基链；R.sup.5是氢或直链或支链烷基；A.sup.2是含有2至6个碳原子的直链或支链、饱和或不饱和的碳氢链；R.sup.6从各种结构中选择，已发现具有中枢神经系统活性。
• ZELESKO, M. J.;MCCOMSEY, D. F.;HAGEMAN, W. E.;NORTEY, S. O.;BAKER, C. A.;+, J. MED. CHEM., 1983, 26, N 2, 230-237
  作者：ZELESKO, M. J.、MCCOMSEY, D. F.、HAGEMAN, W. E.、NORTEY, S. O.、BAKER, C. A.、+

  DOI：——

  日期：——
• INDOLE DERIVATIVES, THEIR PREPARATION AND USE
  申请人：NOVO NORDISK A/S

  公开号：EP0495826A1

  公开（公告）日：1992-07-29
• US5227488A
  申请人：——

  公开号：US5227488A

  公开（公告）日：1993-07-13
• [EN] INDOLE DERIVATIVES, THEIR PREPARATION AND USE
  申请人：NOVO NORDISK A/S

  公开号：WO1991004973A1

  公开（公告）日：1991-04-18

  (EN) Indole derivatives of formula (I) wherein R1, R2, R3 and R4 may be hydrogen or lower alkyl optionally substituted by halogen; X represents oxygen or sulfur; A1 represents a straight or branched alkylene chain containing from 2 to 4 carbon atoms; R5 is hydrogen or a straight or branched alkyl group; A2 is a straight or branched, saturated or unsaturated hydrocarbon chain containing from 2 to 6 carbon atoms; and R6 is selected from a group consisting of various structures, have been found to exhibit central nervous system activities.(FR) Dérivés d'indole de la formule (I), dans laquelle R1, R2, R3 et R4 peuvent être de l'hydrogène ou de l'alkyle inférieur facultativement remplacés par de l'halogène; X représente de l'oxygène ou du soufre, A1 représente une chaîne d'alkylène droite ou ramifiée contenant 2 à 4 atomes de carbone; R5 représente de l'hydrogène ou un groupe alkyle droit ou ramifié; A2 représente une chaîne d'hydrocarbure droite ou ramifiée, saturée ou insaturée, contenant 2 à 4 atomes de carbone; et R6 est choisie dans le groupe composé de diverses structures. On a découvert que les dérivés présentent des activités au niveau du système nerveux central.