3-(3-Bromo-phenyl)-3-methyl-2-methylamino-butyric acid | 676627-44-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(3-Bromo-phenyl)-3-methyl-2-methylamino-butyric acid
• 英文别名: 3-(3-Bromophenyl)-3-methyl-2-(methylamino)butanoic acid
• CAS: 676627-44-4
• 化学式: C₁₂H₁₆BrNO₂
• 分子量: 286.169
• InChiKey: MGHALFQEQDFKCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3-Bromo-phenyl)-3-methyl-2-methylamino-butyric acid 在 N-甲基吗啉 、 lithium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 (E,4S)-4-[[(2S)-2-[[(2R)-3-(3-bromophenyl)-3-methyl-2-(methylamino)butanoyl]amino]-3,3-dimethylbutanoyl]-methylamino]-2,5-dimethylhex-2-enoic acid
  参考文献：
  名称：

  Synthesis and activity of novel analogs of hemiasterlin as inhibitors of tubulin polymerization: modification of the A segment

  摘要：

  Analogs of hemiasterlin (1) and HTI-286 (2), which contain various aromatic rings in the A segment, were synthesized as potential inhibitors of tubulin polymerization. The structure-activity relationships related to stereo- and regio-chemical effects of substituents on the aromatic ring in the A segment were studied. Analogs, which carry a meta-substituted phenyl ring in the A segment show comparable activity for inhibition of tubulin polymerization to 2, as well as in the cell proliferation assay using KB cells containing P-glycoprotein, compared to those of 1 and 2. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.024
• 作为产物：
  描述：

  3-(3-Bromo-phenyl)-3-methyl-2-oxo-butyric acid 在 吡啶硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 3-(3-Bromo-phenyl)-3-methyl-2-methylamino-butyric acid
  参考文献：
  名称：

  Synthesis and activity of novel analogs of hemiasterlin as inhibitors of tubulin polymerization: modification of the A segment

  摘要：

  Analogs of hemiasterlin (1) and HTI-286 (2), which contain various aromatic rings in the A segment, were synthesized as potential inhibitors of tubulin polymerization. The structure-activity relationships related to stereo- and regio-chemical effects of substituents on the aromatic ring in the A segment were studied. Analogs, which carry a meta-substituted phenyl ring in the A segment show comparable activity for inhibition of tubulin polymerization to 2, as well as in the cell proliferation assay using KB cells containing P-glycoprotein, compared to those of 1 and 2. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.024

文献信息

• [EN] HEMIASTERLIN DERIVATIVES FOR CONJUGATION AND THERAPY<br/>[FR] DÉRIVÉS D'HÉMIASTERLINE POUR CONJUGAISON ET THÉRAPIE
  申请人：SUTRO BIOPHARMA INC

  公开号：WO2016123582A1

  公开（公告）日：2016-08-04

  Provided herein are hemiasterlin derivatives, conjugates thereof, compositions comprising the derivatives or conjugates thereof, methods of producing the derivatives and conjugates thereof, and methods of using the derivatives, conjugates, and compositions for the treatment of cell proliferation. The derivatives, conjugates, and compositions are useful in methods of treatment and prevention of cell proliferation and cancer, methods of detection of cell proliferation and cancer, and methods of diagnosis of cell proliferation and cancer. In an embodiment, the hemiasterlin derivatives are according to Formula 1000: or a pharmaceutically acceptable salt, solvate, or tautomer thereof, wherein Ar, L, W1, W4, W5, SG, and R are as described herein.

  本文提供了半星菱素衍生物，以及与之结合的共轭物，包含这些衍生物或共轭物的组合物，生产这些衍生物和共轭物的方法，以及利用这些衍生物、共轭物和组合物治疗细胞增殖的方法。这些衍生物、共轭物和组合物在治疗和预防细胞增殖和癌症的方法中很有用，也可用于检测细胞增殖和癌症的方法，以及诊断细胞增殖和癌症的方法。在一个实施例中，半星菱素衍生物符合公式1000：或其药用可接受的盐、溶剂化合物或互变异构体，其中Ar、L、W1、W4、W5、SG和R如本文所述。
• [EN] IMMUNOMODULATOR ANTIBODY DRUG CONJUGATES AND USES THEREOF<br/>[FR] CONJUGUÉS ANTICORPS-MÉDICAMENT IMMUNOMODULATEURS ET UTILISATIONS ASSOCIÉES
  申请人：SUTRO BIOPHARMA INC

  公开号：WO2020252015A1

  公开（公告）日：2020-12-17

  Provided herein are compounds, trifunctional antibody products thereof, and methods and pharmaceutical compositions for use in treatment of inflammatory and/or proliferative diseases.

  本文提供了化合物、三功能抗体产品以及用于治疗炎症和/或增殖性疾病的方法和药物组合物。
• Method of treating resistant tumors
  申请人：Wyeth Holdings Corporation

  公开号：US20040121965A1

  公开（公告）日：2004-06-24

  The invention provides a method of treating or inhibiting the growth of or eradicating a tumor in a mammal in need thereof wherein said tumor is resistant to at least one chemotherapeutic agent which method comprises providing to said mammal an effective amount of a compound of Formula II or a pharmaceutically acceptable salt thereof.

  本发明提供了一种治疗或抑制哺乳动物体内对至少一种化疗药物产生耐药性的肿瘤生长或根除肿瘤的方法，该方法包括向该哺乳动物提供有效量的公式II化合物或其药学上可接受的盐。
• HEMIASTERLIN DERIVATIVES FOR CONJUGATION AND THERAPY
  申请人：SUTRO BIOPHARMA, INC.

  公开号：US20160257709A1

  公开（公告）日：2016-09-08

  Provided herein are hemiasterlin derivatives, conjugates thereof, compositions comprising the derivatives or conjugates thereof, methods of producing the derivatives and conjugates thereof, and methods of using the derivatives, conjugates, and compositions for the treatment of cell proliferation. The derivatives, conjugates, and compositions are useful in methods of treatment and prevention of cell proliferation and cancer, methods of detection of cell proliferation and cancer, and methods of diagnosis of cell proliferation and cancer. In an embodiment, the hemiasterlin derivatives are according to Formula 1000: or a pharmaceutically acceptable salt, solvate, or tautomer thereof, wherein Ar, L, W 1 , W 4 , W 5 , SG, and R are as described herein.

  本文提供了半天然菌素衍生物及其共轭物，包含这些衍生物或共轭物的组合物，制备这些衍生物和共轭物的方法，以及使用这些衍生物，共轭物和组合物治疗细胞增殖的方法。这些衍生物，共轭物和组合物在治疗和预防细胞增殖和癌症的方法中有用，用于细胞增殖和癌症的检测方法以及细胞增殖和癌症的诊断方法。在一个实施例中，半天然菌素衍生物如公式1000所示：或其药学上可接受的盐，溶剂或互变异构体，其中Ar，L，W1，W4，W5，SG和R如本文所述。