sodium 3-indolylthiolate

• 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: sodium 3-indolylthiolate
• 英文别名: sodium;1H-indole-3-thiolate
• 化学式: C₈H₆NS*Na
• 分子量: 171.198
• InChiKey: BCFKZTLZLVFAMM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.92
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  16.8
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  sodium 3-indolylthiolate 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 2.0h， 生成 ({1-[(Furan-2-yl)methyl]-1H-indol-3-yl}sulfanyl)acetonitrile
  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：

  吲哚-3-基硫氰酸酯 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 sodium 3-indolylthiolate
  参考文献：
  名称：

  Synthesis and evaluation of benzimidazole carbamates bearing indole moieties for antiproliferative and antitubulin activities

  摘要：

  A series of novel benzimidazole carbamates bearing indole moieties with sulphur or selenium atoms connecting the aromatic rings were synthesised and evaluated for their antiproliferative activities against three human cancer cell lines (SGC-7901. A-549 and HT-1080) using an MTT assay. Compounds 10a, 10b, 7a, 7b and 7f showed significant activities against these cell lines. The most potent compound in this series, 10a, was selected to investigate its antitumour mechanism. In addition, molecular docking studies suggested that compound 10a interacts very closely with the nocodazole docking pose through hydrogen bonds at the colchicine binding site of tubulin. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.071

文献信息

• 4-Phenyl-1-piperazinyl, -piperidinyl and -tetrahydropyridyl derivatives
  申请人：H. Lundbeck A/S

  公开号：US20030027832A1

  公开（公告）日：2003-02-06

  The present invention relates to substituted 4 -phenyl- 1 -piperazinyl derivatives having the formula I 1 wherein W is C, CH or N, and the dotted line emanating from W indicates a bond when W is C and no bond when W is N or CH; R 1 and R 2 are independently selected from hydrogen and halogen, provided at least one of R 1 and R 2 is a halogen atom; R 3 is selected from hydrogen, halogen, C 1-6 alkyl, trifluoromethyl, C 1-6 alkoxy, aryloxy, aralkoxy, hydroxy, amino, C 1-6 alkylamino, di(C 1-6 alkyl)amino, nitro and cyano n is 2, 3, 4 or 5; X is CH 2 , O, S, CO, CS, SO or SO 2 ; and Q is a group of formula 2 wherein Z is a chain of 3 to 4 chain members; wherein the chain members are selected from C, CH, CH 2 , CO, N and NH, provided that only one of the chain members may be N or NH, and said chain optionally containing one or two double bonds; hvad med acyl?? R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are independently selected from hydrogen, halogen, C 1-6 alkyl, trifluoromethyl, C 1-6 alkoxy, hydroxy, amino, C 1-6 alkylamino, di(C 1-6 alkyl)amino nitro and cyano; provided that X is not O or S when the group Q is attached via an N atom; and any of its enantiomers and acid addition salts thereof. These compounds have high affinity for D 4 receptors.

  本发明涉及具有式I1的取代4-苯基-1-哌嗪基衍生物，其中W为C、CH或N，从W发出的虚线表示当W为C时为键，当W为N或CH时不为键；R1和R2独立地选择自氢和卤素，只要R1和R2中至少有一个是卤素原子；R3选择自氢、卤素、C1-6烷基、三氟甲基、C1-6烷氧基、芳氧基、芳基氧基、羟基、氨基、C1-6烷基氨基、二(C1-6烷基)氨基、硝基和氰基，n为2、3、4或5；X为CH2、O、S、CO、CS、SO或SO2；Q是式2的一个基团，其中Z是3到4个链成员的链；链成员选择自C、CH、CH2、CO、N和NH，只有一个链成员可以是N或NH，该链可选择性地含有一个或两个双键；acetyl如何？R4、R5、R6、R7、R8、R9和R10独立地选择自氢、卤素、C1-6烷基、三氟甲基、C1-6烷氧基、羟基、氨基、C1-6烷基氨基、二(C1-6烷基)氨基、硝基和氰基；只要通过N原子连接时，X不是O或S；及其任何对映体和酸盐。这些化合物对D4受体具有高亲和力。
• 4-Phenyl-1-piperazinyl, -piperidinyl and-tetrahydropyridyl derivatives
  申请人：Bang-Andersen Benny

  公开号：US20060148815A1

  公开（公告）日：2006-07-06

  The present invention relates to substituted 4-phenyl-1-piperazinyl derivatives having the formula I wherein W is C, CH or N, and the dotted line emanating from W indicates a bond when W is C and no bond when W is N or CH; X is CH 2 , O, S, CO, CS, SO or SO 2 ; and Q is a group of formula wherein Z is a chain of 3 to 4 chain members; wherein the chain members are selected from C, CH, CH 2 , CO, N and NH, provided that only one of the chain members may be N or NH, and said chain optionally containing one or two double bonds; provided that X is not O or S when the group Q is attached via an N atom; and any of its enantiomers and acid addition salts thereof. These compounds have high affinity for D 4 receptors.

  本发明涉及具有以下式子I的取代的4-苯基-1-哌嗪基衍生物： 其中，W为C、CH或N，当W为C时，点线由W发出表示键合，当W为N或CH时，则没有键合；X为CH2、O、S、CO、CS、SO或SO2；Q为以下式子的基团： 其中，Z为3至4个链成员的链，其中链成员从C、CH、CH2、CO、N和NH中选择，只有一个链成员可以是N或NH，并且该链可选择包含一或两个双键；当基团Q通过一个N原子连接时，X不为O或S；以及其任何对映异构体和酸加成盐。这些化合物具有对D4受体的高亲和力。
• 4-PHENYL-1-PIPERAZINYL, -PIPERIDINYL AND -TETRAHYDROPYRIDYL DERIVATIVES
  申请人：H. Lundbeck A/S

  公开号：EP1246817A1

  公开（公告）日：2002-10-09
• 4-Phenyl-piperazinyl, -piperidinyl and tetrahydropyridyl derivatives as dopamine D4 antagonists
  申请人：H. LUNDBECK A/S

  公开号：EP1464641B1

  公开（公告）日：2008-05-14
• US4059583A
  申请人：——

  公开号：US4059583A

  公开（公告）日：1977-11-22