5-苄氧基-1H-吲哚-2-羧酸甲酯 | 55581-41-4

• 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
• 中文名称: 5-苄氧基-1H-吲哚-2-羧酸甲酯
• 英文名称: methyl 5-benzyloxyindole-2-carboxylate
• 英文别名: 5-benzyloxy-1H-indole-2-carboxylic acid methyl ester；methyl 5-(benzyloxy)-1H-indole-2-carboxylate；5-benzyloxy-indole-2-carboxylic acid methyl ester；5-Benzyloxy-indol-2-carbonsaeure-methylester；methyl 5-phenylmethoxy-1H-indole-2-carboxylate
• CAS: 55581-41-4
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: ZLVQXIOLOMFGEE-UHFFFAOYSA-N

物化性质

• 熔点：
  150-151 °C
• 沸点：
  472.3±30.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319
• 储存条件：
  存储条件：2-8°C，避光干燥。

反应信息

• 作为反应物：
  描述：

  5-苄氧基-1H-吲哚-2-羧酸甲酯 在 甲醇 、 palladium on activated charcoal 作用下， 生成 5-羟基-1H-吲哚-2-羧酸甲酯
  参考文献：
  名称：

  17. 5-羟基吲哚

  摘要：

  DOI：

  10.1039/jr9430000049
• 作为产物：
  描述：

  4-硝基间甲苯酚 在 sodium hydroxide 、 乙醚 、 乙醇 、 potassium ethoxide 、 sodium ethanolate 、 iron(II) sulfate 作用下， 生成 5-苄氧基-1H-吲哚-2-羧酸甲酯
  参考文献：
  名称：

  17. 5-羟基吲哚

  摘要：

  DOI：

  10.1039/jr9430000049

文献信息

• Continuous flow thermolysis of azidoacrylates for the synthesis of heterocycles and pharmaceutical intermediates
  作者：Alexander G. O'Brien、François Lévesque、Peter H. Seeberger

  DOI：10.1039/c0cc04481d

  日期：——

  An efficient, safe and scalable procedure for the continuous flow thermolysis of azidoacrylates to yield indoles has been developed and was applied to the synthesis of related heterocycles. The scalability of the process was demonstrated in the continuous flow synthesis of a precursor to the DAAO inhibitor 4H-furo[3,2-b]pyrrole-5-carboxylic acid.

  已经开发了一种有效，安全和可扩展的方法，用于叠氮丙烯酸酯的连续流热解以生成吲哚，并将其用于相关杂环的合成。该方法的可扩展性在DAAO抑制剂4H-呋喃[3,2-b]吡咯-5-羧酸的前体的连续流动合成中得到证明。
• Probing the Subpockets of Factor Xa Reveals Two Binding Modes for Inhibitors Based on a 2-Carboxyindole Scaffold:  A Study Combining Structure-Activity Relationship and X-ray Crystallography
  作者：Marc Nazaré、David W. Will、Hans Matter、Herman Schreuder、Kurt Ritter、Matthias Urmann、Melanie Essrich、Armin Bauer、Michael Wagner、Jörg Czech、Martin Lorenz、Volker Laux、Volkmar Wehner

  DOI：10.1021/jm0490540

  日期：2005.7.1

  remarkably potent factor Xa inhibitor displaying a K(i) value of 0.07 nM. X-ray crystallography of inhibitors bound to factor Xa revealed substituent-dependent switching of the inhibitor binding mode and provided a rationale for the SAR obtained. These results underscore the key role played by the P1 ligand not only in determining the binding affinity of the inhibitor by direct interaction but also in

  描述了一系列结合了中性P1配体的高效能2-羧基吲哚基因子Xa抑制剂之间的结构活性关系，尤其着重于解决因子Xa酶亚口袋的结构要求。通过系统地取代2-羧基吲哚支架与优先的P1和P4取代基来探索与亚口袋的相互作用。在吲哚核上结合最有利的取代基导致发现显示K（i）值为0.07 nM的非常有效的Xa抑制剂。与因子Xa结合的抑制剂的X射线晶体学分析揭示了抑制剂结合模式的取代基依赖性转换，并为获得的SAR提供了理论依据。
• Structural Necessity of Indole C5-O-Substitution of seco-Duocarmycin Analogs for Their Cytotoxic Activity
  作者：Taeyoung Choi、Eunsook Ma

  DOI：10.3390/molecules15117971

  日期：——

  A series of racemic indole C5-O-substituted seco-cyclopropylindole (seco-CI) compounds 1-5 were prepared by coupling in the presence of EDCI of 1-(tert-butyloxycarbonyl)-3-(chloromethyl)indoline (seg-A) with 5-hydroxy-, 5-O-methylsulfonyl, 5-O-aminosulfonyl, 5-O-(N,N-dimethylaminosulfonyl)- and 5-O-benzyl-1H-indole-2-carboxylic acid as seg-B. Compounds 1-5 were tested for cytotoxic activity against four human cancer cell lines (COLO 205, SK-MEL-2, A549, and JEG-3) using a MTT assay. Compounds 2 and 3 with small sized sulfonyl substituents like 5-O-methylsulfonyl and 5-O-aminosulfonyl exhibit a similar level of activity as doxorubicin against all cell lines tested.

  一系列对映体吲哚C5-O取代的seco-环丙基吲哚（seco-CI）化合物1-5是通过在EDCI存在下将1-(叔丁氧基羧基)-3-(氯甲基)吲哚（sEG-A）与5-羟基、5-O-甲基磺酰、5-O-氨基磺酰、5-O-(N,N-二甲基氨基磺酰)和5-O-苄基-1H-吲哚-2-羧酸（作为sEG-B）进行偶联制备的。使用MTT法测试了化合物1-5对四种人癌细胞系（COLO 205、SK-MEL-2、A549和JEG-3）的细胞毒活性。化合物2和3的磺酰取代基较小，如5-O-甲基磺酰和5-O-氨基磺酰，其对所有测试的细胞系表现出与多柔比星相似的活性水平。
• Indole derivatives and their use as MCP-1 antagonist
  申请人：AstraZeneca AB

  公开号：US06737435B1

  公开（公告）日：2004-05-18

  A compound of formula (1) wherein R1 is hydrogen, halo or methoxy, R2 is hydrogen, halo, methyl, ethyl or methoxy; R3 is carboxy, tetrazolyl, or —CONHSO2R4 where R4 is methyl, ethyl, phenyl, 2,5-dimethylisoxazolyl or trifluoromethyl; T is —CH2— or —SO2—; and ring A is 3-chlorophenyl, 4-chlorophenyl, 3-trifluoromethylphenyl, 3,4-dichlorophenyl, 3,4-difluorophenyl, 3-fluoro-4-chlorophenyl, 3-chloro-4-fluorophenyl or 2,3-dichloropyrid-5-yl; or a pharmaceutically acceptable salt or prodrug thereof, as well as pharmaceutical compositions containing them are described and claimed. These compounds and compositions are useful in the treatment of disease mediated by monocyte chemoattractant protein-1 or RANTES (Regulated Upon Activation, Normal T-cell Expressed and Secreted), such as inflammatory disease.

  式（1）的化合物，其中R1为氢，卤素或甲氧基，R2为氢，卤素，甲基，乙基或甲氧基；R3为羧基，四唑基，或-CONHSO2R4，其中R4为甲基，乙基，苯基，2,5-二甲基异噁唑基或三氟甲基；T为-CH2-或-SO2-；环A为3-氯苯基，4-氯苯基，3-三氟甲基苯基，3,4-二氯苯基，3,4-二氟苯基，3-氟-4-氯苯基，3-氯-4-氟苯基或2,3-二氯吡啶-5-基；或其药学上可接受的盐或前药，以及包含它们的药物组合物被描述和声明。这些化合物和组合物在治疗由单核细胞趋化蛋白-1或RANTES（活化后调节的、正常T细胞表达和分泌的）介导的疾病，如炎症性疾病中是有用的。
• Substituted naphthylene compounds exhibiting selective leukotriene
  申请人：Rhone-Poulenc Rorer Pharmaceuticals Inc.

  公开号：US05468898A1

  公开（公告）日：1995-11-21

  This invention relates to bicyclic aryl compounds having selective LTB.sub.4 antagonist properties and comprising an amido substituent, a substituent group having a terminal carboxylic acid or derivative thereof and a lipophilic substituent, and to methods for the treatment of disorders which result from LTB.sub.4 activity and pharmaceutical compositions including such compounds.

  本发明涉及具有选择性LTB.sub.4拮抗剂特性的双环芳基化合物，其包括一个酰胺取代基，一个具有末端羧酸或其衍生物的取代基团和一个亲脂性取代基，并涉及使用这些化合物治疗由LTB.sub.4活性引起的疾病的方法和包括这些化合物的制药组合物。