3-氨基-5-羧基-N-甲基苯甲酰胺 | 1954-96-7

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 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: 3-氨基-5-羧基-N-甲基苯甲酰胺
• 中文别名: 3-氨基-5-[(甲氨基)羰基]苯甲酸；5-氨基-n-甲基异邻氨甲酰苯甲酸
• 英文名称: 3-amino-5-(methylcarbamoyl)benzoic acid
• 英文别名: 5-Amino-isophthalsaeure-mono-methylamid；3-amino-5-[(methylamino)carbonyl]benzoic acid；5-amino-N-methylisophthalamic acid；3-N-methylcarbamoyl-5-amino-benzoic acid
• CAS: 1954-96-7
• 化学式: C₉H₁₀N₂O₃
• mdl: MFCD00215980
• 分子量: 194.19
• InChiKey: SIIWAVHOCVSSKA-UHFFFAOYSA-N

物化性质

• 熔点：
  227-230 °C
• 沸点：
  442.7±40.0 °C(Predicted)
• 密度：
  1.343±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

制备方法与用途

化学性质：结晶状固体，熔点为225-228℃。

用途：作为异泛影（新泛影）的中间体。

生产方法：首先使用异酞酸（间苯二甲酸），以发烟硝酸进行硝化反应生成5-硝基异酞酸。随后，在硫酸催化下与甲醇酯化，再通过氢氧化钠部分水解得到5-硝基异酞酸单甲酯单钠。最后，经甲胺胺化并还原硝基，最终制得目标产物。

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  5-氨基-3-羧基-2,4,6-三碘-N-甲基苯甲酰胺	N-Methyl-2.4.6-trijod-5-amino-isophthalamidsaeure	2280-89-9	C9H7I3N2O3	571.88

反应信息

• 作为反应物：
  描述：

  3-氨基-5-羧基-N-甲基苯甲酰胺 生成 2,4,6-tribromo-3-N-methylcarbamoyl-5-amino-benzoic acid
  参考文献：
  名称：

  BONNEMAIN, B.;HARDOUIN, J. -C.;LAUTROU, J. -F.

  摘要：

  DOI：

文献信息

• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSÉS CHIMIQUES
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2013096151A1

  公开（公告）日：2013-06-27

  The invention is directed to substituted quinoline derivatives. Specifically, the invention is directed to compounds according to Formula (I): wherein R1, R2, R3; R4; and R5 are defined herein. The compounds of the invention are inhibitors of lactate dehydrogenase A and can be useful in the treatment of cancer and diseases associated with tumor cell metabolism, such as cancer, and more specifically cancers of the breast, colon, prostate and lung. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting lactate dehydrogenase A activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  该发明涉及取代喹啉衍生物。具体而言，该发明涉及符合以下式（I）的化合物：其中R1、R2、R3；R4；和R5在此处被定义。该发明的化合物是乳酸脱氢酶A的抑制剂，可用于治疗癌症和与肿瘤细胞代谢相关的疾病，如乳腺癌、结肠癌、前列腺癌和肺癌等。因此，该发明进一步涉及包含该发明化合物的药物组合物。该发明还进一步涉及使用该发明化合物或包含该发明化合物的药物组合物来抑制乳酸脱氢酶A活性和治疗相关疾病的方法。
• Process for the preparation of
  申请人：Mallinckrodt, Inc.

  公开号：US05013865A1

  公开（公告）日：1991-05-07

  An improved process for preparing a compound selected from among 2,4,6-triiodo-5-amino-N-alkylisophthalamic acid, salts thereof, esters thereof, 2,4,6-triiodo-5-amino-isophthalamide, 2,4,6-triiodo-5-amino-N-hydroxyalkyl-isophthalamide and 2,4,6-triiodo-5-amino-N,N'-bishydroxyalkyl-isophthalamide. A substrate selected from among 5-amino-N-alkylisophthalamic acid, salts thereof, esters thereof 5-amino-isophthalamide, 5-amino-N-hydroxyalkyl-isophthalamide and 5-amino-N,N'-bishydroxyalkylisophthalamide is reacted with an iodine halide in an aqueous reaction medium. In accordance with the improvement, the substrate and a source of the iodine halide are added to the reaction medium at such relative rates that, at any instant substantially throughout the addition cycle, the substrate is present in stoichoimetric excess over the iodine halide, but the difference between the cumulative amount of the substrate that has been added to the medium at such instant, expressed as a proportion of the total ultimate charge of the substrate, and the cumulative amount of the source of iodine halide that has been added to the medium at such instant, expressed as a proportion of the total ultimate charge of the source of iodine halide, does not exceed 10%. When the substrate is 5-amino-isophthalamide, 5-amino-N-hydroxyalkyl-isophthalamide or 5-amino-N,N'-bishydroxyalkyl-isophthalamide, the cumulative amount of the iodine halide may be in stoichiometric excess of not more than about 10% of the substrate computed on the same basis. Further improvements, respectively comprising incorporation of an alkaline buffer composition and operation at relative high dilution, are also disclosed.

  一种改进的制备方法，用于制备从2,4,6-三碘-5-氨基-N-烷基异苯二甲酸、其盐、酯，2,4,6-三碘-5-氨基异苯酰胺，2,4,6-三碘-5-氨基-N-羟基烷基异苯酰胺和2,4,6-三碘-5-氨基-N，N'-双羟基烷基异苯酰胺中选择的化合物。选择从5-氨基-N-烷基异苯二甲酸、其盐、酯，5-氨基异苯酰胺，5-氨基-N-羟基烷基异苯酰胺和5-氨基-N，N'-双羟基烷基异苯二甲酰胺中的底物，在水性反应介质中与碘卤素反应。根据改进，底物和碘卤素来源以相对速率加入反应介质中，以使在任何瞬间，底物在摩尔比上相对于碘卤素处于化学计量过量状态，但在该瞬间底物的累积添加量与碘卤素来源的累积添加量之间的差值，以底物的总最终电荷的比例表示，不超过10％。当底物为5-氨基异苯酰胺，5-氨基-N-羟基烷基异苯酰胺或5-氨基-N，N'-双羟基烷基异苯酰胺时，碘卤素的累积添加量可以在计算相同基础上不超过底物的摩尔比的化学计量过量不超过10％。此外，还公开了进一步的改进，分别包括加入碱性缓冲剂组成和在相对高稀释下操作。
• BONNEMAIN, B.;HARDOUIN, J. -C.;LAUTROU, J. -F.
  作者：BONNEMAIN, B.、HARDOUIN, J. -C.、LAUTROU, J. -F.

  DOI：——

  日期：——
• PROCESS FOR THE PREPARATION OF 2,4,6-TRIIODO-5-AMINO-N-ALKYLISOPHTHALAMIC ACID
  申请人：MALLINCKRODT, INC.

  公开号：EP0408654B1

  公开（公告）日：1995-05-24
• PROCESS FOR THE PREPARATION OF 2,4,6-TRIIODO-5-AMINO-N-ALKYLISOPHTHALAMIC ACID AND 2,4,6-TRIIODO-5-AMINO-ISOPHTHALAMIDE COMPOUNDS
  申请人：MALLINCKRODT, INC.

  公开号：EP0484328A1

  公开（公告）日：1992-05-13