methyl 5-methoxy-1-methyl-1H-indole-2-carboxylate | 67929-87-7

• 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: methyl 5-methoxy-1-methyl-1H-indole-2-carboxylate
• 英文别名: Methyl 5-methoxy-1-methyl-1H-indolecarboxylate；methyl 5-methoxy-1-methylindole-2-carboxylate
• CAS: 67929-87-7
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: ATBRZWKEUADOQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 5-methoxy-1-methyl-1H-indole-2-carboxylate 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 5-methoxy-1-methyl-1H-indole-2-carbaldehyde
  参考文献：
  名称：

  金(I)-催化2-(烯基)吲哚碳环化合成咔唑

  摘要：

  通过金（I）催化的（Z）-2-（烯基）吲哚的分子内加氢芳基化实现了咔唑的新合成方案，收率良好。必需的 (Z)-2-(烯炔基) 吲哚是通过三甲基镓促进的、Z-选择性 Wittig 烯化 N-烷基吲哚-2-甲醛与炔丙基叶立德的立体选择性合成的。在这些反应条件下，具有烷基和芳族基团的底物具有良好的耐受性。

  DOI：

  10.1055/s-0030-1259537
• 作为产物：
  描述：

  5-甲氧基吲哚-2-羧酸 在 硫酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 methyl 5-methoxy-1-methyl-1H-indole-2-carboxylate
  参考文献：
  名称：

  金(I)-催化2-(烯基)吲哚碳环化合成咔唑

  摘要：

  通过金（I）催化的（Z）-2-（烯基）吲哚的分子内加氢芳基化实现了咔唑的新合成方案，收率良好。必需的 (Z)-2-(烯炔基) 吲哚是通过三甲基镓促进的、Z-选择性 Wittig 烯化 N-烷基吲哚-2-甲醛与炔丙基叶立德的立体选择性合成的。在这些反应条件下，具有烷基和芳族基团的底物具有良好的耐受性。

  DOI：

  10.1055/s-0030-1259537

文献信息

• [EN] PYRROLOBENZODIAZEPINE PRODRUGS AND ANTIBODY CONJUGATES THEREOF<br/>[FR] PROMÉDICAMENTS DE PYRROLOBENZODIAZÉPINE ET CONJUGUÉS D'ANTICORPS DE CEUX-CI
  申请人：GENENTECH INC

  公开号：WO2018031662A1

  公开（公告）日：2018-02-15

  The invention relates generally to pyrrolobenzodiazepine monomer and dimer prodrugs having a glutathione-activated disulfide prodrug moiety, a DT-diaphorase-activated quinone prodrug moiety or a reactive oxygen species-activated aryl boronic acid or aryl boronic ester prodrug moiety. The invention further relates to pyrrolobenzodiazepine prodrug dimer-antibody conjugates.

  这项发明涉及具有谷胱甘肽活化二硫键前药基团、DT-二氢呋喃酮酶活化醌前药基团或活化氧化物种的芳基硼酸或芳基硼酯前药基团的吡咯苯并二氮杂环烷单体和二聚体前药。该发明还涉及吡咯苯并二氮杂环烷前药二聚体-抗体共轭物。
• Indole-2-carboxamides as inhibitors of cell adhesion
  申请人：Warner-Lambert Company

  公开号：US05424329A1

  公开（公告）日：1995-06-13

  3-Substituted-indole-2-carboxamides are described as agents which inhibit leukocyte adherence to vascular endothelium and, as such, are effective therapeutic agents for treating inflammatory diseases. Certain of these compounds are novel and methods of manufacture are also described. Certain of the indole-2-carboxamides also inhibit the activation of human immunodeficiency virus (HIV), latent in infected humans.

  3-取代吲哚-2-羧酰胺被描述为抑制白细胞粘附到血管内皮的药物，并且作为有效的治疗药物用于治疗炎症性疾病。其中一些化合物是新颖的，并且还描述了其制造方法。其中一些吲哚-2-羧酰胺也能抑制潜伏在感染人体内的人类免疫缺陷病毒（HIV）的激活。
• 2,5-Dihydro-1,2-thiazino(5,6-b)indole-3-carboxamide-1,1-dioxides and
  申请人：Boehringer Ingelheim GmbH

  公开号：US04137313A1

  公开（公告）日：1979-01-30

  Compounds of the formula ##STR1## WHEREIN R.sub.1 is hydrogen, methyl or ethyl; R.sub.2 is methyl or ethyl; Y is hydrogen, fluorine, chlorine, bromine, methoxy, methyl, ethyl or trifluoromethyl; and Ar is 2-thiazolyl which may have one or two methyl or ethyl substituents attached thereto; 5,6-dihydro-4H-cyclopentathiazol-2-yl; 4,5,6,7-tetrahydro-2-benzothiazolyl; 2-benzothiazolyl; 3-isothiazolyl which may have a methyl substituent attached thereto; 2-pyridyl which may have a methyl or hydroxyl substituent attached thereto; 3-pyridyl; 4-pyridyl; 4-pyrimidinyl; pyrazinyl; 2-benzimidazolyl; 2-oxazolyl which may have a methyl substituent attached thereto; 2-benzoxazolyl; or phenyl which may have a fluoro, chloro, bromo, methyl, ethyl, trifluoromethyl or methoxy substituent attached thereto; and non-toxic, pharmacologically acceptable salts thereof formed with inorganic or organic bases. The compounds as well as their salts are useful as antiphlogistics and blood platelet aggregation inhibitors.

  式为 ##STR1## 的化合物，其中 R.sub.1 是氢、甲基或乙基；R.sub.2 是甲基或乙基；Y 是氢、氟、氯、溴、甲氧基、甲基、乙基或三氟甲基；Ar 是2-噻唑基，可能具有一个或两个连接的甲基或乙基取代基；5,6-二氢-4H-环戊噻唑-2-基；4,5,6,7-四氢-2-苯并噻唑基；2-苯并噻唑基；3-异噻唑基，可能具有一个连接的甲基取代基；2-吡啶基，可能具有一个连接的甲基或羟基取代基；3-吡啶基；4-吡啶基；4-吡咪啶基；吡嗪基；2-苯并咪唑基；2-噁唑基，可能具有一个连接的甲基取代基；2-苯并噁唑基；或苯基，可能具有一个氟、氯、溴、甲基、乙基、三氟甲基或甲氧基取代基；以及与无机或有机碱形成的非毒性、药理学上可接受的盐。这些化合物及其盐可用作抗炎药和血小板聚集抑制剂。
• Phosphoramide compounds
  申请人：——

  公开号：US20030008850A1

  公开（公告）日：2003-01-09

  The invention provides a compound of formula I: 1 wherein R 1 , R a , R b , R c , and R d have any of the values defined in the specification, as well as pharmaceutical compositions comprising such compounds or salts. The compounds are useful for treating cancer in animals.

  本发明提供了一种I式化合物：1，其中R1、Ra、Rb、Rc和Rd的任何值均定义在规范中，以及包含这种化合物或盐的药物组合物。这些化合物对于治疗动物的癌症具有用处。
• From Far West to East: Joining the Molecular Architecture of Imidazole-like Ligands in HO-1 Complexes
  作者：Giuseppe Floresta、Antonino Nicolò Fallica、Vincenzo Patamia、Valeria Sorrenti、Khaled Greish、Antonio Rescifina、Valeria Pittalà

  DOI：10.3390/ph14121289

  日期：——

  HO-1 overexpression has been reported in several cases/types of human malignancies. Unfortunately, poor clinical outcomes are reported in most of these cases, and the inhibition of HO-1 is considered a valuable and proven anticancer approach. To identify novel hit compounds suitable as HO-1 inhibitors, we report here a fragment-based approach where ligand joining experiments were used. The two most important parts of the classical structure of the HO-1 inhibitors were used as a starting point, and 1000 novel compounds were generated and then virtually evaluated by structure and ligand-based approaches. The joining experiments led us to a novel series of indole-based compounds. A synthetic pathway for eight selected molecules was designed, and the compounds were synthesized. The biological activity revealed that some molecules reach the micromolar activity, whereas molecule 4d inhibits the HO-1 with an IC50 of 1.03 μM. This study suggested that our joining approach was successful, and a novel hit compound was generated. These results are ongoing for further development.

  HO-1过度表达已被报道在多种人类恶性肿瘤中。不幸的是，在大多数这些情况下，报道了糟糕的临床结果，因此HO-1的抑制被认为是一种有价值且经过验证的抗癌方法。为了寻找适合作为HO-1抑制剂的新型化合物，我们在这里报告了一种基于片段的方法，其中使用了配体连接实验。将HO-1抑制剂的经典结构的两个最重要的部分作为起点，生成了1000种新型化合物，并通过结构和配体基础方法进行了虚拟评估。连接实验使我们得到了一系列新型的吲哚基化合物。设计了八种选择分子的合成途径，并合成了这些化合物。生物活性显示，一些分子达到了微摩尔活性，而分子4d以1.03μM的IC50抑制了HO-1。这项研究表明，我们的连接方法是成功的，并生成了一种新型的命中化合物。这些结果正在进行进一步的开发。