2-<(2-carboxyphenyl)amino>-4-methylbenzoic acid | 63329-46-4

• 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: 2-<(2-carboxyphenyl)amino>-4-methylbenzoic acid
• 英文别名: 2-((2-Hydroxycarbonyl)anilino)-4-methylbenzoic acid；4-methyl-2,2'-iminodibenzoic acid；2-[(2-carboxyphenyl)amino]-4-methylbenzoic acid；2-(2-Carboxyanilino)-4-methylbenzoic acid
• CAS: 63329-46-4
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: QFTSYOOBTREBMZ-UHFFFAOYSA-N

物化性质

• 熔点：
  302-304 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  475.9±40.0 °C(Predicted)
• 密度：
  1.378±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-<(2-carboxyphenyl)amino>-4-methylbenzoic acid 在 吡啶 、 氯化亚砜 、 硫酸 、 N,N-二甲基甲酰胺 、 三氯化磷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.75h， 生成 9-[4-(methanesulfonamido)-2-methoxyanilino]-N,6-dimethylacridine-4-carboxamide
  参考文献：
  名称：

  Potential antitumor agents. Part 38. 3-Substituted 5-carboxamido derivatives of amsacrine

  摘要：

  The synthesis and biological evaluation of a series of 3-substituted 5-carboxamido derivatives of amsacrine (m-AMSA) are described. This series was developed as the result of previous quantitative structure-activity relationship (QSAR) studies of the antitumor activity of 9-anilinoacridine derivatives. In agreement with these studies, this class of compounds, possessing a variety of small nonpolar groups at the 3-position, together with very hydrophilic carboxamido groups at the 5-position, have high in vivo activity against animal leukemia models.

  DOI：

  10.1021/jm00365a013
• 作为产物：
  描述：

  邻氨基苯甲酸 、 2-溴-4-甲基苯甲酸 在 copper(I) oxide 、 铜 、 potassium carbonate 作用下， 以 乙二醇乙醚 为溶剂， 反应 0.5h， 以96%的产率得到2-<(2-carboxyphenyl)amino>-4-methylbenzoic acid
  参考文献：
  名称：

  Potential antitumor agents. Part 38. 3-Substituted 5-carboxamido derivatives of amsacrine

  摘要：

  The synthesis and biological evaluation of a series of 3-substituted 5-carboxamido derivatives of amsacrine (m-AMSA) are described. This series was developed as the result of previous quantitative structure-activity relationship (QSAR) studies of the antitumor activity of 9-anilinoacridine derivatives. In agreement with these studies, this class of compounds, possessing a variety of small nonpolar groups at the 3-position, together with very hydrophilic carboxamido groups at the 5-position, have high in vivo activity against animal leukemia models.

  DOI：

  10.1021/jm00365a013

文献信息

• 3,5-Disubstituted-4'-(9-acridinylamino)-methane-sulfon-m-anisidide
  申请人：Development Finance Corporation of New Zealand

  公开号：US04472582A1

  公开（公告）日：1984-09-18

  3,5-Disubstituted-4'-(9-acridinylamino)-methane-sulfon-m-anisidide compounds represented by the general formula ##STR1## in which R.sup.2 and R.sup.3 represent, respectively, --CH.sub.3 and --CONHCH.sub.3, --CH.sub.3 and --CONHCH.sub.2 CONH.sub.2, --Cl and --CONHCH.sub.2 CONH.sub.2, --CONHCH.sub.3 and --CH.sub.3 ; and acid addition salts thereof have unexpectedly high antitumor activity in leukemic animals and low or no direct mutagenicity.

  该文描述了一类化合物，其通用式为##STR1##，其中R.sup.2和R.sup.3分别代表--CH.sub.3和--CONHCH.sub.3，--CH.sub.3和--CONHCH.sub.2 CONH.sub.2，--Cl和--CONHCH.sub.2 CONH.sub.2，--CONHCH.sub.3和--CH.sub.3。这些化合物的酸加成盐在白血病动物中具有意外的高抗肿瘤活性，并且低或没有直接致突变性。
• Compounds having antitumour properties, process for their preparation, these compounds for use as antitumour agents and pharmaceutical compositions containing them
  申请人：DEVELOPMENT FINANCE CORPORATION OF NEW ZEALAND

  公开号：EP0025705A1

  公开（公告）日：1981-03-25

  Compounds represented by the general formula in which R1 represents-CH3, -CH2CH3 or -(CH2)2 CH3; R2 represents -CONHR4, -F, -Cl, -Br, -I, -CF3, -N02, -NH2, -CH3, -OCH3 or-NHCOCH3, and R3 represents -CONHR4, -H, -CH3 or -OCH3, with the proviso that at least one of R2 and R3 represents -CONHR4; and R4 represents H, or -CH3, -CH2CH3, -(CH2)2CH3, -(CH2)3CH3 or - CH2CH(CH3)2, each optionally substituted with hydroxyl, amine and/or amide functions; and acid addition salts thereof have antitumour properties.

  由通式表示的化合物 其中 R1 代表-CH3、- 或-(CH2)2 ； R2 代表-CONHR4、-F、-Cl、-Br、-I、 -CF3、-N02、-NH2、- 、-O 或-NHCO ，以及 R3 代表-CONHR4、-H、- 或-O ，但 R2 和 R3 中至少有一个代表-CONHR4； 和 R4 代表 H、或- 、- 、-( )2 、-( )3 或- CH( )2，各自任选被羟基、胺和/或酰胺官能团取代； 及其酸加成盐具有抗肿瘤特性。
• Stewart, Georgina M.; Rewcastle, Gordon W.; Denny, William A., Australian Journal of Chemistry, 1984, vol. 37, # 9, p. 1939 - 1950
  作者：Stewart, Georgina M.、Rewcastle, Gordon W.、Denny, William A.

  DOI：——

  日期：——
• DENNY, W. A.;ATWELL, G. J.;BAGULEY, B. C., J. MED. CHEM., 1983, 26, N 11, 1619-1625
  作者：DENNY, W. A.、ATWELL, G. J.、BAGULEY, B. C.

  DOI：——

  日期：——
• REWCASTLE, G. W.;ATWELL, G. J.;CHAMBERS, D.;BAGULEY, B. C.;DENNY, W. A., J. MED. CHEM., 1986, 29, N 4, 472-477
  作者：REWCASTLE, G. W.、ATWELL, G. J.、CHAMBERS, D.、BAGULEY, B. C.、DENNY, W. A.

  DOI：——

  日期：——