3-(4-aminophenoxy)propionic acid methyl ester | 130198-72-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-aminophenoxy)propionic acid methyl ester
• 英文别名: 3-(4-amino-phenoxy)-propionic acid methyl ester；Methyl 3-(4-aminophenoxy)propanoate
• CAS: 130198-72-0
• 化学式: C₁₀H₁₃NO₃
• mdl: MFCD12779273
• 分子量: 195.218
• InChiKey: BUXRTYMRNUWARN-UHFFFAOYSA-N

物化性质

• 沸点：
  344.9±22.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-aminophenoxy)propionic acid methyl ester 在 盐酸 、 sodium azide 、 氯甲酸乙酯 、 溶剂黄146 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 丙酮 、 苯 为溶剂， 反应 51.59h， 生成 4-(2-氨基乙氧基)-N,N-二(2-氯乙基)苯胺
  参考文献：
  名称：

  DNA-directed alkylating agents. 3. Structure-activity relationships for acridine-linked aniline mustards: consequences of varying the length of the linker chain

  摘要：

  Four series of acridine-linked aniline mustards have been prepared and evaluated for in vitro cytotoxicity, in vivo antitumor activity, and DNA cross-linking ability. The anilines were attached to the DNA-intercalating acridine chromophores by link groups (-O-, -CH2-, -S-, and -SO2-) of widely varying electronic properties, providing four series of widely differing mustard reactivity where the alkyl chain linking the acridine and mustard moieties was varied from two to five carbons. Relationships were sought between chain length and biological properties. Within each series, increasing the chain length did not alter the reactivity of the alkylating moiety but did appear to position it differently on the DNA, since cross-linking ability (measured by agarose gel assay) altered with chain length, being maximal with the C4 analogue. The in vivo antitumor activities of the compounds depended to some extent on the reactivity of the mustard, with the least reactive SO2 compounds being inactive. However, DNA-targeting did appear to allow the use of less reactive mustards, since the S-linked acridine mustards showed significant activity whereas the parent S-mustard did not. Within each active series, the most active compound was the C4 homologue, suggesting some relationship between activity and extent of DNA alkylation.

  DOI：

  10.1021/jm00173a016
• 作为产物：
  描述：

  methyl 3-(4-nitrophenoxy)propionate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 3-(4-aminophenoxy)propionic acid methyl ester
  参考文献：
  名称：

  DNA-directed alkylating agents. 3. Structure-activity relationships for acridine-linked aniline mustards: consequences of varying the length of the linker chain

  摘要：

  Four series of acridine-linked aniline mustards have been prepared and evaluated for in vitro cytotoxicity, in vivo antitumor activity, and DNA cross-linking ability. The anilines were attached to the DNA-intercalating acridine chromophores by link groups (-O-, -CH2-, -S-, and -SO2-) of widely varying electronic properties, providing four series of widely differing mustard reactivity where the alkyl chain linking the acridine and mustard moieties was varied from two to five carbons. Relationships were sought between chain length and biological properties. Within each series, increasing the chain length did not alter the reactivity of the alkylating moiety but did appear to position it differently on the DNA, since cross-linking ability (measured by agarose gel assay) altered with chain length, being maximal with the C4 analogue. The in vivo antitumor activities of the compounds depended to some extent on the reactivity of the mustard, with the least reactive SO2 compounds being inactive. However, DNA-targeting did appear to allow the use of less reactive mustards, since the S-linked acridine mustards showed significant activity whereas the parent S-mustard did not. Within each active series, the most active compound was the C4 homologue, suggesting some relationship between activity and extent of DNA alkylation.

  DOI：

  10.1021/jm00173a016

文献信息

• [EN] TRIAZOLO[4,5-D]PYRIMIDINE DERIVATIVES FOR THE TREATMENT OF DISEASES SUCH AS CANCER<br/>[FR] DÉRIVÉS DE TRIAZOLO[4,5-D]PYRIMIDINE POUR LE TRAITEMENT DE MALADIES TELLES QUE LE CANCER
  申请人：MERCK PATENT GMBH

  公开号：WO2014135244A1

  公开（公告）日：2014-09-12

  Compounds of the formula I, in which R1 and R2 have the meanings indicated in Claim 1, are inhibitors of GCN2, and can be employed, inter alia, for the treatment of cancer.

  式I的化合物，其中R1和R2具有权利要求1中指示的含义，是GCN2的抑制剂，可用于治疗癌症。
• [EN] MACROCYCLES AS KINASE INHIBITORS<br/>[FR] MACROCYCLES UTILISÉS EN TANT QU'INHIBITEURS DE KINASES
  申请人：MERCK PATENT GMBH

  公开号：WO2014180524A1

  公开（公告）日：2014-11-13

  Compounds of the formula I in which X, Y, Q1, M, Q2 and B have the meanings indicated in Claim 1, are inhibitors of GCN2, and can be employed, inter alia, for the treatment of cancer.

  式I中X、Y、Q1、M、Q2和B具有权利要求1中所指示的含义的化合物是GCN2的抑制剂，可用于治疗癌症。
• THERAPEUTIC COMPOUNDS FOR DISEASES AND DISORDERS
  申请人：Klein Christine

  公开号：US20090253768A1

  公开（公告）日：2009-10-08

  Pyrrole derivatives are disclosed as agents for the treatment and prevention of neuropathies and neurodegenerative diseases characterized by the presence of axonal blockages, impaired axonal transport or impaired trafficking of vesicles in neurons.

  吡咯衍生物被披露为治疗和预防神经病变和神经退行性疾病的药物，这些疾病的特征是存在轴突阻塞、轴突运输受损或神经元中囊泡运输受损。
• PYRROLE DERIVATIVES AS THERAPEUTIC COMPOUNDS
  申请人：Weiner Warren S.

  公开号：US20080249158A1

  公开（公告）日：2008-10-09

  Novel pyrrole derivatives are disclosed as Aβ 42 -lowering agents for the treatment and prevention of neurodegenerative disorders characterized by the formation or accumulation of amyloid plaques comprising the Aβ 42 peptide.

  本发明揭示了新型吡咯衍生物，作为Aβ42降低剂，用于治疗和预防神经退行性疾病，其特征是形成或积累包含Aβ42肽的淀粉样斑块。
• Pyrrole Derivatives As Therapeutic Compounds
  申请人：Weiner Warren S.

  公开号：US20100216862A1

  公开（公告）日：2010-08-26

  Novel pyrrole derivatives are disclosed as Aβ 42 -lowering agents for the treatment and prevention of neurodegenerative disorders characterized by the formation or accumulation of amyloid plaques comprising the Aβ 42 peptide.

  本发明揭示了一种新型吡咯衍生物，作为降低Aβ42的药物，用于治疗和预防由Aβ42肽形成或积累的淀粉样斑块所特征的神经退行性疾病。