1-(2-oxo-2-phenylethyl)-1H-indole-3-carboxaldehyde | 171734-90-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-oxo-2-phenylethyl)-1H-indole-3-carboxaldehyde
• 英文别名: 1-phenacylindole-3-carbaldehyde
• CAS: 171734-90-0
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: HJVAYUYPNYYOBZ-UHFFFAOYSA-N

物化性质

• 沸点：
  482.3±25.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  39.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-oxo-2-phenylethyl)-1H-indole-3-carboxaldehyde 生成 5-(1-phenacylindol-3-yl)methylene-2,4-thiazolidinedione
  参考文献：
  名称：

  Thiazolidinedione derivatives, method for preparing the derivatives and

  摘要：

  以下是通用公式（I）所代表的噻唑烷二酮衍生物：##STR1## 其中虚线代表单键或双键，噻唑烷二酮环残基连接到吲哚环的2-、3-、4-、5-和6-位置中的任一位置，R代表从氢原子和烷基、烯基、炔基、苯基、芳基烷基、杂环烷基、芳基磺酰基和芳基氨基甲酰基组成的群中选择的一个群！或其药学上可接受的盐表现出降低血糖水平和降低血液中脂质浓度的优异效果，因此可用作治疗糖尿病的治疗剂。这些衍生物及其药学上可接受的盐几乎没有任何副作用。

  公开号：

  US05811439A1
• 作为产物：
  描述：

  1-<2-(2-bromophenyl)-2-oxoethyl>-1H-indole-3-carboxaldehyde 在 四(三苯基膦)钯 、 potassium acetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 1-(2-oxo-2-phenylethyl)-1H-indole-3-carboxaldehyde
  参考文献：
  名称：

  Desarbre, Eric; Merour, Jean-Yves, Heterocycles, 1995, vol. 41, # 9, p. 1987 - 1998

  摘要：

  DOI：

文献信息

• [EN] INDOLYL-PIPERIDINYL BENZYLAMINES AS BETA-TRYPTASE INHIBITORS<br/>[FR] INDOLYL-PIPÉRIDINYL BENZYLAMINES INHIBITRICES DE LA BÊTA-TRYPTASE
  申请人：SANOFI SA

  公开号：WO2011079102A1

  公开（公告）日：2011-06-30

  The present invention discloses and claims a series of substituted indolyl-piperidinyl benzylamines of formula (I), wherein R1, R2 and R3 are as described herein. More specifically, the compounds of this invention are inhibitors of β-tryptase and are, therefore, useful as pharmaceutical agents. Additionally, this invention also discloses methods of preparation of substituted indolyl-piperidinyl benzylamines. In one of the embodiments, there is provided the compounds of formula (I) wherein R3 is (II).

  本发明公开并要求一系列取代的吲哚基-哌啶基苄胺化合物，其公式为（I），其中R1、R2和R3如本文所述。更具体地说，本发明的化合物是β-tryptase的抑制剂，因此可用作药物制剂。此外，本发明还公开了取代的吲哚基-哌啶基苄胺的制备方法。在其中一个实施例中，提供了公式（I）的化合物，其中R3是（II）。
• Thiazolidinedione derivatives, process for their preparation and pharmaceutical compositions containing them
  申请人：TOBISHI PHARMACEUTICAL CO., LTD.

  公开号：EP0780389A1

  公开（公告）日：1997-06-25

  A thiazolidinedione derivative represented by the following general formula (I): [wherein the dotted line represents a single bond or a double bond , the thiazolidinedione ring residue is linked to either of 2-, 3-, 4-, 5- and 6-positions on the indole ring and R represents a group selected from the group consisting of hydrogen atom and alkyl, alkenyl, alkynyl, phenyl, aralkyl, heterocycloalkyl, arylsulfonyl and arylaminocarbonyl groups] or a pharmaceutically acceptable salt thereof exhibits excellent effects of reducing the blood sugar level and of reducing the lipid concentration in blood and is accordingly useful as a therapeutic agent for treating diabates mellitus. These derivatives and pharmaceutically acceptable salt thereof are almost free of any side effect.

  由以下通式（I）代表的噻唑烷二酮衍生物： [其中虚线代表单键或双键，噻唑烷二酮环残基与吲哚环上的 2-、3-、4-、5-和 6-位中的任一个相连，R 代表选自氢原子和烷基、烯基、炔基、苯基、芳基、杂环烷基、芳基磺酰基和芳基氨基羰基组成的基团]或其药用盐、或其药学上可接受的盐具有极佳的降低血糖水平和血脂浓度的效果，因此可用作治疗糖尿病的药物。这些衍生物及其药学上可接受的盐几乎没有任何副作用。
• Discovery of certain benzyl/phenethyl thiazolidinone-indole hybrids as potential anti-proliferative agents: Synthesis, molecular modeling and tubulin polymerization inhibition study
  作者：Dilep Kumar Sigalapalli、Venkatesh Pooladanda、Priti Singh、Manasa Kadagathur、Sravanthi Devi Guggilapu、Jaya Lakshmi Uppu、Neelima D. Tangellamudi、Pavan Kumar Gangireddy、Chandraiah Godugu、Nagendra Babu Bathini

  DOI：10.1016/j.bioorg.2019.103188

  日期：2019.11

  A series of certain benzyl/phenethyl thiazolidinone-indole hybrids were synthesized for the study of anti-proliferative activity against A549, NCI-H460 (lung cancer), MDA-MB-231 (breast cancer), HCT-29 and HCT-15 (colon cancer) cell lines by using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT). We found that compound G37 displayed highest cytotoxicity with IC50 value of 0.92 +/- 0.12 mu M towards HCT-15 cancer cell line among all the synthesized compounds. Moreover, compound G37 was also tested on normal human lung epithelial cells (L132) and was found to be safe in contrast to HCT-15 cells. The lead compound G37 showed significant G2/M phase arrest in HCT-15 cells. Additionally, compound G37 significantly inhibited tubulin polymerization with IC50, value of 2.92 +/- 0.23 mu M. Mechanistic studies such as acridine orange/ethidium bromide (AO/EB) dual staining, DAPI nuclear staining, annexinV/propidium iodide dual staining, donogenic growth inhibition assays inferred that compound G37 induced apoptotic cell death in HCT-15 cells. Moreover, loss of mitochondrial membrane potential with elevated intracellular ROS levels was observed by compound G37. These compounds bind at the active pocket of the alpha/beta-tubulin with higher number of stable hydrogen bonds, hydrophobic and arene-cation interactions confirmed by molecular modeling studies.
• US5811439A
  申请人：——

  公开号：US5811439A

  公开（公告）日：1998-09-22
• Desarbre, Eric; Merour, Jean-Yves, Heterocycles, 1995, vol. 41, # 9, p. 1987 - 1998
  作者：Desarbre, Eric、Merour, Jean-Yves

  DOI：——

  日期：——