Ethyl 3-amino-5,6-dimethoxyindol-2-carboxylate

• 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: Ethyl 3-amino-5,6-dimethoxyindol-2-carboxylate
• 英文别名: ethyl 3-amino-5,6-dimethoxy-1H-indole-2-carboxylate
• 化学式: C₁₃H₁₆N₂O₄
• mdl: MFCD04171550
• 分子量: 264.281
• InChiKey: LUIAZGKXCGSIJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 3-amino-5,6-dimethoxyindol-2-carboxylate 在 盐酸 、 三氯氧磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 34.0h， 生成 4-chloro-2-(furan-2-yl)-7,8-dimethoxy-5H-pyrimido[5,4-b]indole
  参考文献：
  名称：

  Synthesis and anti-HIV-1 activities of new pyrimido[5,4-b]indoles

  摘要：

  A set of new pyrimido[5,4-b]indole derivatives that are structurally related to some non-nucleoside HIV-I reverse transcriptase inhibitors were synthesized and biologically evaluated for their activity as inhibitors of wild and mutant HIV-1 RT types in an 'in vitro' recombinant HIV-1 RT screening assay, as well as anti-infectives in HLT4lacZ-1(IIIB) cells. Preliminary structure-activity relationships suggest that activity is promoted by simultaneous substitution in positions 2 and 4, especially when chains of alkyldiamine type are present, and by electron-releasing substituents (methoxy) in positions 7 and 8. The inactivity or the very low activity of title derivatives does not suggest interest in AIDS therapy. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00035-x
• 作为产物：
  描述：

  (2-Cyano-4,5-dimethoxy-phenylamino)-acetic acid ethyl ester 、 potassium tert-butylate 、 在 氮气 、 乙酸乙酯 、 magnesium sulfate 、 silica gel 、 二氯甲烷 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以to provide 61.9 mg (49%) of the title compound as a solid的产率得到Ethyl 3-amino-5,6-dimethoxyindol-2-carboxylate
  参考文献：
  名称：

  Interleukin-4 gene expression inhibitors

  摘要：

  本发明揭示和声明了一类吲哚和苯并(b)噻吩衍生物，用于治疗过敏、哮喘、鼻炎、皮炎、B细胞淋巴瘤、肿瘤以及与细菌、鼻病毒或呼吸道合胞病毒(RSV)感染相关的疾病。本发明的化合物由式(I)定义：其中X、Y、Z、R1、R2和R3如规范中所定义；或其药学上可接受的盐。在本发明的优选实施方式中，还揭示和声明本发明的化合物能够调节T辅助细胞(Th)、Th1/Th2，并能够抑制白细胞介素-4(IL-4)信息的转录，IL-4的释放或IL-4的产生。

  公开号：

  US20040006123A1

文献信息

• Indole derivatives as interleukin -4 gene expression inhibitors
  申请人：——

  公开号：US20040010029A1

  公开（公告）日：2004-01-15

  This invention discloses and claims a new class of indole derivatives for use in treating allergy, asthma, rhinitis, dermatitis, B-cell lymphomas, tumors and diseases associated with bacterial, rhinovirus or respiratory syncytial virus (RSV) infections. It has now been found that the compounds of this invention are capable of modulating T helper (Th) cells, Th1/Th2, and thereby capable of inhibiting the transcription of interleukin-4 (IL-4) message, IL-4 release or IL-4 production.

  这项发明揭示并声明了一类新的吲哚衍生物，用于治疗过敏、哮喘、鼻炎、皮炎、B细胞淋巴瘤、肿瘤以及与细菌、鼻病毒或呼吸道合胞病毒（RSV）感染相关的疾病。现在已经发现，该发明的化合物能够调节T辅助细胞（Th）细胞、Th1 / Th2，从而能够抑制白细胞介素-4（IL-4）信息的转录、IL-4释放或IL-4的产生。
• Interleukin-4 gene expression inhibitors
  申请人：——

  公开号：US20040006123A1

  公开（公告）日：2004-01-08

  This invention discloses and claims a class of indole and benzo(b)thiophene derivatives for use in treating allergy, asthma, rhinitis, dermatitis, B-cell lymphomas, tumors and diseases associated with bacterial, rhinovirus or respiratory syncytial virus (RSV) infections. The compounds of this invention are defined by the Formula (I): 1 wherein X, Y, Z, R 1 , R 2 and R 3 are as defined in the specification; or a pharmaceutically acceptable salt thereof. In preferred embodiments of this invention it is also disclosed and claimed that the compounds of this invention are capable of modulating T helper (Th) cells, Th1/Th2, and thereby capable of inhibiting the transcription of interleukin-4 (IL-4) message, IL-4 release or IL-4 production.

  本发明揭示和声明了一类吲哚和苯并(b)噻吩衍生物，用于治疗过敏、哮喘、鼻炎、皮炎、B细胞淋巴瘤、肿瘤以及与细菌、鼻病毒或呼吸道合胞病毒(RSV)感染相关的疾病。本发明的化合物由式(I)定义：其中X、Y、Z、R1、R2和R3如规范中所定义；或其药学上可接受的盐。在本发明的优选实施方式中，还揭示和声明本发明的化合物能够调节T辅助细胞(Th)、Th1/Th2，并能够抑制白细胞介素-4(IL-4)信息的转录，IL-4的释放或IL-4的产生。
• Indole derivatives as interleukin-4 gene expression inhibitors
  申请人：Aventis Pharmaceuticals Inc.

  公开号：US07169925B2

  公开（公告）日：2007-01-30

  This invention discloses and claims a new class of indole derivatives for use in treating allergy, asthma, rhinitis, dermatitis, B-cell lymphomas, tumors and diseases associated with bacterial, rhinovirus or respiratory syncytial virus (RSV) infections. It has now been found that the compounds of this invention are capable of modulating T helper (Th) cells, Th1/Th2, and thereby capable of inhibiting the transcription of interleukin-4 (IL-4) message, IL-4 release or IL-4 production.

  本发明揭示和声明了一类新的吲哚衍生物，用于治疗过敏、哮喘、鼻炎、皮炎、B细胞淋巴瘤、肿瘤以及与细菌、鼻病毒或呼吸道合胞病毒（RSV）感染相关的疾病。现已发现，本发明的化合物能够调节T辅助细胞（Th）细胞、Th1/Th2细胞，并因此能够抑制白细胞介素-4（IL-4）信息的转录、IL-4的释放或IL-4的产生。
• US7169925B2
  申请人：——

  公开号：US7169925B2

  公开（公告）日：2007-01-30
• Synthesis and anti-HIV-1 activities of new pyrimido[5,4-b]indoles
  作者：Isidro Merino、Antonio Monge、Marı́a Font、Juan José Martı́nez de Irujo、Elena Alberdi、Esteban Santiago、Isidro Prieto、Juan José Lasarte、Pablo Sarobe、Francisco Borrás

  DOI：10.1016/s0014-827x(99)00035-x

  日期：1999.4

  A set of new pyrimido[5,4-b]indole derivatives that are structurally related to some non-nucleoside HIV-I reverse transcriptase inhibitors were synthesized and biologically evaluated for their activity as inhibitors of wild and mutant HIV-1 RT types in an 'in vitro' recombinant HIV-1 RT screening assay, as well as anti-infectives in HLT4lacZ-1(IIIB) cells. Preliminary structure-activity relationships suggest that activity is promoted by simultaneous substitution in positions 2 and 4, especially when chains of alkyldiamine type are present, and by electron-releasing substituents (methoxy) in positions 7 and 8. The inactivity or the very low activity of title derivatives does not suggest interest in AIDS therapy. (C) 1999 Elsevier Science S.A. All rights reserved.