methyl 4-(N-2,5-dihydroxybenzylamino)benzoate | 140674-76-6

• 物质功能分类: 生物化工 - 抑制剂
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-(N-2,5-dihydroxybenzylamino)benzoate
• 英文别名: Tyrphostin AG 957；N-(2,5-dihydroxylbenzyl)-4-methoxycarbonyl aniline；Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester；methyl 4-[(2,5-dihydroxyphenyl)methylamino]benzoate
• CAS: 140674-76-6
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: QSFREBZMBNRGOK-UHFFFAOYSA-N

物化性质

• 沸点：
  504.2±45.0 °C(Predicted)
• 密度：
  1.337±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-(N-2,5-dihydroxybenzylamino)benzoate 在 碘 作用下， 以 水 、 乙腈 为溶剂， 以70%的产率得到methyl 4-{[(3,6-dioxocyclohexa-1,4-dien-1-yl)methyl]amino}benzoate
  参考文献：
  名称：

  11C labelling of AG957?a potential tyrphostin radiotracer for PET

  摘要：

  碳-11标记的4-(N-2,5-二羟基苄基)氨基甲基苯甲酸酯（AG957），一种用于成像bcr-abl受体的潜在放射性示踪剂，已被合成。[11C]AG957通过使用[11C]CH3I标记4-氨基苯甲酸制备，从而获得了相应的高产率的[11C]甲酯。随后，氨基与2,5-二羟基苯甲醛缩合形成相应的席夫碱。使用NaBH3CN还原此化合物，得到了总衰减校正放射性化学产率为65-75%（基于11CH3I）的[11C]AG957，平均比放射性为40 GBq/μmol（1.1 Ci/μmol）。从结束标记（EOB）到制剂的总合成时间为45分钟。在生理pH下，该化合物被发现足够稳定，适合进行体外和体内研究。版权所有 © 2002 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.546
• 作为产物：
  描述：

  desmethyl AG957 在 硫酸 作用下， 以 甲醇 为溶剂， 以65%的产率得到methyl 4-(N-2,5-dihydroxybenzylamino)benzoate
  参考文献：
  名称：

  Synthesis and biological evaluation of platensic alcohol as an adamantane surrogate in antitumor drug lead adaphostin

  摘要：

  DOI：

  10.1016/j.bmcl.2021.128270

文献信息

• 11C labelling of AG957?a potential tyrphostin radiotracer for PET
  作者：Uwe Ackermann、Henri J. Tochon-Danguy、Kenneth Young、John I. Sachinidis、J. Gordon Chan、Andrew M. Scott

  DOI：10.1002/jlcr.546

  日期：2002.2

  Carbon-11 labelled 4-(N-2,5-dihydroxybenzyl)amino methyl benzoate (AG957), a potential radiotracer for imaging bcr–abl receptors was synthesized. [11C]AG957 was prepared by labelling 4-aminobenzoic acid using [11C]CH3I, which affords the corresponding [11C] methyl ester in excellent yields. Subsequent condensation of the amino group with 2,5-dihydroxy-benzaldehyde formed the respective Schiff base. Reduction of this compound with NaBH3CN gave [11C]AG957 in overall decay corrected radiochemical yield of 65–75% (based on 11CH3I) with an average specific radioactivity of 40 GBq/μmol (1.1 Ci/μmol). The total synthesis time from EOB including formulation was 45 min. At physiological pH, the compound was found to be sufficiently stable for in vitro and in vivo investigations. Copyright © 2002 John Wiley & Sons, Ltd.

  碳-11标记的4-(N-2,5-二羟基苄基)氨基甲基苯甲酸酯（AG957），一种用于成像bcr-abl受体的潜在放射性示踪剂，已被合成。[11C]AG957通过使用[11C]CH3I标记4-氨基苯甲酸制备，从而获得了相应的高产率的[11C]甲酯。随后，氨基与2,5-二羟基苯甲醛缩合形成相应的席夫碱。使用NaBH3CN还原此化合物，得到了总衰减校正放射性化学产率为65-75%（基于11CH3I）的[11C]AG957，平均比放射性为40 GBq/μmol（1.1 Ci/μmol）。从结束标记（EOB）到制剂的总合成时间为45分钟。在生理pH下，该化合物被发现足够稳定，适合进行体外和体内研究。版权所有 © 2002 John Wiley & Sons, Ltd.
• THERAPEUTIC BENEFIT OF SUBOPTIMALLY ADMINISTERED CHEMICAL COMPOUNDS
  申请人：BROWN Dennis M.

  公开号：US20160045502A1

  公开（公告）日：2016-02-18

  The present invention describes methods and compositions for improving the therapeutic efficacy of therapeutic agents previously limited by suboptimal therapeutic performance by either improving efficacy as monotherapy or reducing side effects. Such methods and compositions are particularly applicable to mustard-based alkylating agents such as uracil mustard and analogs, derivatives, or prodrugs thereof, including 6-methyluracil mustard and 6-ethyluracil mustard.

  本发明描述了一种改善先前受到治疗性能不佳限制的治疗剂的治疗效果的方法和组合物，通过改善单药疗法的功效或减少副作用。这种方法和组合物特别适用于芥子碱基烷基化剂，例如尿嘧啶芥和其类似物、衍生物或前药，包括6-甲基尿嘧啶芥和6-乙基尿嘧啶芥。
• Compositions and methods to improve the therapeutic benefit of indirubin and analogs thereof, including meisoindigo
  申请人：Brown Dennis M.

  公开号：US10383847B2

  公开（公告）日：2019-08-20

  The present invention describes methods and compositions for improving the therapeutic efficacy of therapeutically active agents previously limited by suboptimal therapeutic performance by either improving efficacy as monotherapy or reducing side effects. Such methods and compositions are particularly applicable to therapeutically active agents selected from the group consisting of: (i) indirubin; (ii) an analog of indirubin; (iii) a derivative of indirubin or of an analog of indirubin; and (iv) a pharmaceutical composition comprising indirubin, an analog of indirubin, or a derivative of indirubin or of an analog of indirubin, especially meisoindigo. In particular, the therapeutically active agents selected from the group consisting of: (i) indirubin; (ii) an analog of indirubin; (iii) a derivative of indirubin or of an analog of indirubin; and (iv) a pharmaceutical composition comprising indirubin, an analog of indirubin, or a derivative of indirubin or of an analog of indirubin, especially meisoindigo, are effective Nek9 inhibitors. The active agent, such as meisoindigo, can act as a Nek9 inhibitor. The active agent can be used together with Nek9 inhibitors or agents that inhibit the expression of Nek9.

  本发明描述了通过提高单一疗法的疗效或减少副作用来提高以前受次优治疗性能限制的治疗活性制剂的疗效的方法和组合物。这种方法和组合物特别适用于选自以下组别的治疗活性剂：(i) 靛红素；(ii) 靛红素的类似物；(iii) 靛红素或靛红素类似物的衍生物；(iv) 包含靛红素、靛红素类似物或靛红素或靛红素类似物衍生物的药物组合物，特别是甲异靛。特别是，选自以下组别的治疗活性剂是有效的 Nek9 抑制剂：(i) 靛红素；(ii) 靛红素的类似物；(iii) 靛红素的衍生物或靛红素的类似物；以及 (iv) 由靛红素、靛红素的类似物或靛红素的衍生物或靛红素的类似物，特别是 meisoindigo 组成的药物组合物。活性剂，如 meisoindigo，可作为 Nek9 抑制剂。活性剂可与 Nek9 抑制剂或抑制 Nek9 表达的制剂一起使用。
• Use of dianhydrogalactitol and analogs and derivatives thereof to treat recurrent malignant glioma or progressive secondary brain tumor
  申请人：DelMar Pharmaceuticals, Inc.

  公开号：US11026914B2

  公开（公告）日：2021-06-08

  Methods and compositions suitable for the treatment of malignancies such as recurrent glioma and progressive secondary brain tumor are disclosed. These methods employ a hexitol derivative such as dianhydrogalactitol, a derivative or analog of dianhydrogalactitol, diacetyldianhydrogalactitol, or a derivative or analog of diacetyldianhydrogalactitol. The compositions can include such hexitol derivatives.

  本发明公开了适用于治疗复发性胶质瘤和进行性继发性脑瘤等恶性肿瘤的方法和组合物。这些方法采用己糖醇衍生物，如二氢半乳糖醇、二氢半乳糖醇的衍生物或类似物、二乙酰二氢半乳糖醇或二乙酰二氢半乳糖醇的衍生物或类似物。组合物可以包括此类己糖醇衍生物。
• Ackermann, U.; Tochon-Danguy, H. J.; Young, K., Journal of labelled compounds and radiopharmaceuticals, 2001, vol. 44, p. S307 - S309
  作者：Ackermann, U.、Tochon-Danguy, H. J.、Young, K.、Sachinidis, J.、Chan, J. G.、Scott, A. M.

  DOI：——

  日期：——