2-(2,4-二氨基苯基)乙酸 | 79637-84-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(2,4-二氨基苯基)乙酸
• 英文名称: 2,4-diaminophenylacetic acid
• 英文别名: 2-(2,4-Diaminophenyl)acetic acid
• CAS: 79637-84-6
• 化学式: C₈H₁₀N₂O₂
• 分子量: 166.18
• InChiKey: KHZHJGIOIIUHOO-UHFFFAOYSA-N

物化性质

• 熔点：
  193 °C
• 沸点：
  431.2±30.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  89.3
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2922499990

反应信息

• 作为反应物：
  描述：

  2-(2,4-二氨基苯基)乙酸 在 四氢吡咯 、 盐酸 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 6.25h， 生成 (E)-N-(3-benzylidene-2-oxoindolin-6-ylcarbamoyl)-4-methoxybenzamide
  参考文献：
  名称：

  Novel acylureidoindolin-2-one derivatives as dual Aurora B/FLT3 inhibitors for the treatment of acute myeloid leukemia

  摘要：

  A series of 6-acylureido derivatives containing a 3-(pyrrol-2-ylmethylidene)indolin-2-one scaffold were synthesized as potential dual Aurora B/FLT3 inhibitors by replacing the 6-arylureido moiety in 6-arylureidoindolin-2-one-based multi-kinase inhibitors. (Z)-N-(2-(pyrrolidin-l-yl)ethyl)-5-((6-(3-(2-fluoro-4-methoxybenzoyflureido)-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide (54) was identified as a dual Aurora B/FLT3 inhibitor (IC50 = 0.4 nM and 0.5 nM, respectively). Compound 54 also exhibited potent cytotoxicity with single-digit nanomolar IC50 values against the FLT3 mutant-associated human acute myeloid leukemia (AML) cell lines MV4-11 (FLT3-ITD) and MOLM-13 (FLT3-ITD). Compound 54 also specifically induced extrinsic apoptosis by inhibiting the phosphorylation of the Aurora B and FLT3 pathways in MOLM-13 cells. Compound 54 had a moderate pharmacokinetic profile. The mesylate salt of 54 efficiently inhibited tumor growth and reduced the mortality of BALB/c nude mice (subcutaneous xenograft model) that had been implanted with AML MOLM-13 cells. Compound 54 is more potent than sunitinib not only against FLT3-WT AML cells but also active against sunitinib-resistant FLT3-ITD AML cells. This study demonstrates the significance of dual Aurora B/FLT3 inhibitors for the development of potential agents to treat AML. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.108
• 作为产物：
  描述：

  2,4-二硝基苯乙酸 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 2-(2,4-二氨基苯基)乙酸
  参考文献：
  名称：

  (Z)-1-(3-((1H-Pyrrol-2-yl)methylene)-2-oxindolin-6-yl)-3-(isoxazol-3-yl)脲衍生物的发现作为新型和口服高效用于潜在结直肠癌免疫治疗的 CSF-1R 抑制剂

  摘要：

  通过阻断 CSF-1/CSF-1R 信号转导抑制肿瘤相关巨噬细胞的极化或存活已成为癌症免疫治疗的一种有前景的策略。在此，设计了一系列( Z )-1-(3-((1 H -pyrrol-2-yl)methylene)-2-oxoindolin-6-yl)-3-(isoxazol-3-yl)脲衍生物，合成并评估为用于结直肠癌免疫治疗的新型和口服高效 CSF-1R 抑制剂。在这些衍生物中，发现化合物21具有优异的 CSF-1R 抑制活性 (IC 50 = 2.1 nM) 和对结肠直肠癌细胞的有效抗增殖活性。化合物21通过抑制巨噬细胞的迁移、将 M2 样巨噬细胞重编程为 M1 表型和增强抗肿瘤免疫力来抑制结直肠癌的进展。更重要的是，化合物21作为单一药物，在体内抗结直肠癌疗效显着优于PLX3397，突出了结直肠癌免疫治疗的有希望的候选者。

  DOI：

  10.1021/acs.jmedchem.1c01184

文献信息

• NON-NUCLEOSIDE ANTI-HEPACIVIRUS AGENTS AND USES THEREOF
  申请人：Boyd A. Vincent

  公开号：US20070021434A1

  公开（公告）日：2007-01-25

  The present dislcosure provides amide-based, non-nucleoside compounds having antiviral activity against Hepacivirus, such as hepatitis C virus (HCV), methods and intermediates for synthesizing such compounds, and methods of using the compounds in a variety of contexts, including in the treatment and prevention of viral infections. The present dislcosure also provides methods for identifying amide-based, non-nucleoside compounds having antiviral activity.

  本公开提供了基于酰胺的非核苷类化合物，具有抗Hepacivirus活性，例如丙型肝炎病毒（HCV），合成这类化合物的方法和中间体，以及在各种情境中使用这些化合物的方法，包括在治疗和预防病毒感染中的应用。本公开还提供了识别具有抗病毒活性的基于酰胺的非核苷类化合物的方法。
• COMPOSITIONS AND METHODS FOR TREATING HYPERPROLIFERATIVE DISEASE
  申请人：Cameron Dale Russell

  公开号：US20080171783A1

  公开（公告）日：2008-07-17

  The present disclosure provides amide-based, non-nucleoside compounds having an inhibitory activity against endogenous polymerases, such as polymerase alpha and polymerase gamma. This disclosure further provides uses of treating hyperproliferative diseases or disorders, such as benign or malignant neoplasms, and more specifically cancers that are sensitive to inhibition of polymerase alpha and polymerase gamma.

  本公开提供了基于酰胺的非核苷类化合物，具有对内源聚合酶（如聚合酶α和聚合酶γ）的抑制活性。本公开进一步提供了用于治疗过度增殖性疾病或疾病的用途，例如良性或恶性肿瘤，更具体地是对聚合酶α和聚合酶γ抑制敏感的癌症。
• INDOLIN-2-ONE DERIVATIVES AS PROTEIN KINASE INHIBITORS
  申请人：ANNJI PHARMACEUTICAL CO., LTD.

  公开号：US20130281451A1

  公开（公告）日：2013-10-24

  A novel class of indoline-2-one derivatives are disclosed. These compounds are protein kinase inhibitors which are useful for treating hyperproliferative diseases such as cancer.

  揭示了一类新型的吲哚啉-2-酮衍生物。这些化合物是蛋白激酶抑制剂，可用于治疗癌症等过度增殖性疾病。
• Discovery of (<i>Z</i>)-1-(3-((1<i>H</i>-Pyrrol-2-yl)methylene)-2-oxoindolin-6-yl)-3-(isoxazol-3-yl)urea Derivatives as Novel and Orally Highly Effective CSF-1R Inhibitors for Potential Colorectal Cancer Immunotherapy
  作者：Qi Lv、Xiang Pan、Dan Wang、Quanjin Rong、Ben Ma、Xiaolong Xie、Yinan Zhang、Junwei Wang、Lihong Hu

  DOI：10.1021/acs.jmedchem.1c01184

  日期：2021.12.9

  colorectal cancer immunotherapy. Among these derivatives, compound 21 was found to possess excellent CSF-1R inhibitory activity (IC50 = 2.1 nM) and potent antiproliferative activity against colorectal cancer cells. Compound 21 inhibited the progression of colorectal cancer by suppressing the migration of macrophages, reprograming M2-like macrophages to the M1 phenotype, and enhancing the antitumor immunity

  通过阻断 CSF-1/CSF-1R 信号转导抑制肿瘤相关巨噬细胞的极化或存活已成为癌症免疫治疗的一种有前景的策略。在此，设计了一系列( Z )-1-(3-((1 H -pyrrol-2-yl)methylene)-2-oxoindolin-6-yl)-3-(isoxazol-3-yl)脲衍生物，合成并评估为用于结直肠癌免疫治疗的新型和口服高效 CSF-1R 抑制剂。在这些衍生物中，发现化合物21具有优异的 CSF-1R 抑制活性 (IC 50 = 2.1 nM) 和对结肠直肠癌细胞的有效抗增殖活性。化合物21通过抑制巨噬细胞的迁移、将 M2 样巨噬细胞重编程为 M1 表型和增强抗肿瘤免疫力来抑制结直肠癌的进展。更重要的是，化合物21作为单一药物，在体内抗结直肠癌疗效显着优于PLX3397，突出了结直肠癌免疫治疗的有希望的候选者。
• Compositions of lipopeptide antibiotic derivatives and methods of use thereof
  申请人：Cameron R. Dale

  公开号：US20050153876A1

  公开（公告）日：2005-07-14

  The present invention provides derivatives of lipopeptide antibiotics that display antimicrobial activity against microorganisms, methods and compounds for synthesizing such antimicrobial derivatives and analogues, and methods of using the compounds in a variety of contexts, including in the treatment and prevention of microbial infections.

  本发明提供了脂肽类抗生素的衍生物，对微生物显示出抗菌活性，包括合成这种抗微生物衍生物和类似物的方法和化合物，以及在多种情况下使用这些化合物的方法，包括在治疗和预防微生物感染中使用。