2-(indolin-5-yl)acetic acid methyl ester | 188111-62-8

• 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: 2-(indolin-5-yl)acetic acid methyl ester
• 英文别名: methyl indoline-5-acetate；methyl 2-(indolin-5-yl)acetate；Methyl 2-(2,3-dihydro-1H-indol-5-yl)acetate
• CAS: 188111-62-8
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: VHCHZAYZABZJOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(indolin-5-yl)acetic acid methyl ester 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 生成 methyl 1-(5-hydroxypentanoyl)indoline-5-acetate
  参考文献：
  名称：

  Photorelease of Carboxylic Acids from 1-Acyl-7-nitroindolines in Aqueous Solution:  Rapid and Efficient Photorelease of l-Glutamate¹

  摘要：

  DOI：

  10.1021/ja990931e
• 作为产物：
  描述：

  methyl 1-acetylindoline-5-acetate 在 甲醇 、 硫酸 、 乙酸乙酯 、 disodium;carbonate 、 cyclohexane, ethyl acetate 作用下， 以 盐酸 为溶剂， 反应 6.0h， 以to give the title compound as a brown oil (0.40 g)的产率得到2-(indolin-5-yl)acetic acid methyl ester
  参考文献：
  名称：

  Arylethanolamine derivatives and their use as agonists of atypical

  摘要：

  本发明涉及公式（I）的苯乙醇胺衍生物，其中R.sup.1代表芳基基团，该基团可以选择地被卤素、羟基、C.sub.1-6-烷氧基、C.sub.1-6-烷基、硝基、氰基、羟甲基和三氟甲基中的一个或多个取代基取代; R.sup.2代表氢或C.sub.1-6-烷基; R.sup.3代表一个(A)基团，其中环被选择自C.sub.1-6-烷基、卤素、三氟甲基和C.sub.1-6-烷氧基的一个到四个进一步取代基取代; 或R.sup.3代表一个(B)基团，其中芳香环可以选择地被最多三个进一步的C.sub.1-6-烷基、卤素、三氟甲基和C.sub.1-6-烷氧基取代; R.sup.4代表氢或C.sub.1-6-烷基; R.sup.5代表ZCH.sub.2CO.sub.2H，其中Z代表键或O; Y代表(CH.sub.2).sub.n，其中n为1-3; 以及其生理上可接受的衍生物的制备方法; 以及它们在通过非典型β-肾上腺素受体激动剂改善的情况的治疗中的用途。

  公开号：

  US06048872A1

文献信息

• Synthesis and characterisation of13C and15N isotopomers of a 1-acyl-7-nitroindoline
  作者：John E. T. Corrie、Andreas Barth、George Papageorgiou

  DOI：10.1002/jlcr.494

  日期：2001.8

  Efficient methods are described for synthesis of isotopomers of the water-soluble, photolabile 1-acyl-7-nitroindoline 5 with either 13C in the carbonyl of the acyl substituent or 15N in the nitro group. The isotopic incorporations were verified by IR difference spectroscopy coupled with flash photolysis.

  本文描述了合成水溶性、光敏性的1-酰基-7-硝基吲哚5的同位素体的高效方法，其中酰基的羰基位置包含13C，或者硝基位置包含15N。通过红外差谱光谱学结合闪光光解技术验证了同位素的掺入。
• 1-Acyl-7-nitroindoline derivatives, their preparation and their use as photocleavable precursors
  申请人：Medical Research Council

  公开号：US06765014B1

  公开（公告）日：2004-07-20

  Photoreleasable compounds comprising a caging moiety linked to an effector moiety represented by structural formula (I) wherein R1 is hydrogen; C1-10 alkyl or substituted alkyl; O(CH2)n—Y; N(COZ)(CH2)mY; or N[(CH2)mY′[(CH2)NY]; R2 and R3 are independently selected from: hydrogen; C1-10 alkyl or substituted alkyl; or R2 and R3 together are cycloalkyl; R4 is hydrogen; C1-10 alkyl or substituted alkyl; phenyl or substituted phenyl; (CH2)nY; or (CH2)mO(CH2)nY; wherein m and n are independently between 1 and 10; Y and Y′ are independently selected from hydrogen, CO2H or salts thereof or OPO32−, Z is hydrogen or C1-10 alkyl or substituted alkyl; and, X is an effector moiety or a group capable of being coupled or converted to an effector moiety, which are capable of releasing the effector moiety on irradiation, typically by flash irradiation with UV light. The photoreleasable compounds can therefor be used to deliver biologically active effector moieties such as neuroactive amino acids or metal chelators to sites where their activity is required.

  含有一个与结构式（I）所代表的效应子结构式相连的光释放化合物，其中R1为氢；C1-10烷基或取代烷基；O(CH2)n—Y；N(COZ)(CH2)mY；或N[(CH2)mY′[(CH2)NY]; R2和R3分别选择自：氢；C1-10烷基或取代烷基；或R2和R3一起为环烷基；R4为氢；C1-10烷基或取代烷基；苯基或取代苯基；(CH2)nY；或(CH2)mO(CH2)nY；其中m和n分别在1和10之间；Y和Y′分别选择自氢、CO2H或其盐或OPO32−，Z为氢或C1-10烷基或取代烷基；X为效应子或能够与效应子偶联或转化的基团，能够在照射下释放效应子，通常通过紫外光的闪烁照射。因此，这些光释放化合物可用于将生物活性效应子，如神经活性氨基酸或金属螯合剂，输送到需要其活性的部位。
• [EN] SUBSTITUTED CONDENSED PYRIMIDINE COMPOUNDS<br/>[FR] COMPOSÉS DE PYRIMIDINE CONDENSÉS SUBSTITUÉS
  申请人：GRUENENTHAL GMBH

  公开号：WO2014170020A1

  公开（公告）日：2014-10-23

  The invention relates to novel substituted condensed pyrimidine compounds of general formula (I) in which the chemical groupings, substituents and indices are as defined in the description, and to their use as medicaments, in particular as medicaments for the treatment of conditions and diseases that can be treated by inhibition of the PDE4 enzyme.

  本发明涉及通式(I)的新型取代的稠合嘧啶化合物，其中化学基团、取代基和指数如说明书中所定义，以及它们作为药物的用途，特别是作为治疗可通过抑制PDE4酶治疗的病症和疾病的药物。
• Synthesis and Photolytic Assessment of Nitroindolinyl-Caged Calcium Ion Chelators
  作者：George Papageorgiou、John E. T. Corrie

  DOI：10.3390/molecules27092645

  日期：——

  Neuroactive amino acids derivatised at their carboxylate groups with a photolabile nitroindolinyl group are highly effective reagents for the sub-µs release of neuroactive amino acids in physiological solutions. However, the same does not apply in the case of calcium ion chelators. In this study, nitroindolinyl-caged BAPTA is found to be completely photostable, whereas nitroindolinyl-caged EDTA photolyses only when saturated with calcium ions.

  使用光敏硝基吲哚基衍生的神经活性氨基酸，其羧酸基团高效释放亚微秒级神经活性氨基酸在生理溶液中。然而，对于钙离子螯合剂并非如此。在这项研究中，发现硝基吲哚基囚禁的BAPTA是完全光稳定的，而硝基吲哚基囚禁的EDTA只有在饱和钙离子时才会光解。
• Arylethanolamine derivatives and their use as agonists of atypical
  申请人：Glaxo Wellcome Inc.

  公开号：US06048872A1

  公开（公告）日：2000-04-11

  The present invention relates to phenethanolamine derivatives of formula (I) wherein R.sup.1 represents an aryl group optionally substituted by one or more substituents selected from halogen, hydroxy, C.sub.1-6 -alkoxy, C.sub.1-6 -alkyl, nitro, cyano, hydroxymethyl and trifluoromethyl; R.sup.2 represents hydrogen or C.sub.1-6 -alkyl; R.sup.3 represents a group (A) where the ring is substituted by one to four further substituents selected from C.sub.1-6 -alkyl, halogen, trifluoromethyl, and C.sub.1-6 -alkoxy; or R.sup.3 represents a group (B) where the aromatic ring is optionally substituted by up to three further substituents selected from C.sub.1-6 -alkyl, halogen, trifluoromethyl, and C.sub.1-6 -alkoxy; R.sup.4 represents hydrogen, or C.sub.1-6 -alkyl; R.sup.5 represents ZCH.sub.2 CO.sub.2 H wherein Z represents a bond, or O; Y represents (CH.sub.2).sub.n where n is 1-3; and physiologically acceptable derivatives thereof; to process for their preparation; and their use in the treatment of conditions susceptible of amelioration by an atypical beta-adrenoceptor agonist.

  本发明涉及公式（I）的苯乙醇胺衍生物，其中R.sup.1代表芳基基团，该基团可以选择地被卤素、羟基、C.sub.1-6-烷氧基、C.sub.1-6-烷基、硝基、氰基、羟甲基和三氟甲基中的一个或多个取代基取代; R.sup.2代表氢或C.sub.1-6-烷基; R.sup.3代表一个(A)基团，其中环被选择自C.sub.1-6-烷基、卤素、三氟甲基和C.sub.1-6-烷氧基的一个到四个进一步取代基取代; 或R.sup.3代表一个(B)基团，其中芳香环可以选择地被最多三个进一步的C.sub.1-6-烷基、卤素、三氟甲基和C.sub.1-6-烷氧基取代; R.sup.4代表氢或C.sub.1-6-烷基; R.sup.5代表ZCH.sub.2CO.sub.2H，其中Z代表键或O; Y代表(CH.sub.2).sub.n，其中n为1-3; 以及其生理上可接受的衍生物的制备方法; 以及它们在通过非典型β-肾上腺素受体激动剂改善的情况的治疗中的用途。