4-(((吡啶-3-基甲氧基)羰基氨基)甲基)苯甲酸 | 241809-79-0

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 环羧酸
• 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: 4-(((吡啶-3-基甲氧基)羰基氨基)甲基)苯甲酸
• 英文名称: 4-((((pyridin-3-ylmethoxy)carbonyl)amino)methyl)benzoic acid
• 英文别名: 4-[N-(pyridine-3-methoxycarbonyl)]aminomethyl benzoic acid；4-[(pyridin-3-ylmethoxycarbonylamino)methyl]benzoic acid
• CAS: 241809-79-0
• 化学式: C₁₅H₁₄N₂O₄
• 分子量: 286.287
• InChiKey: HZUDHRTWQOKGOX-UHFFFAOYSA-N

物化性质

• 沸点：
  548.3±50.0 °C(Predicted)
• 密度：
  1.316±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  88.5
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2933399090
• 储存条件：
  室温、密封、干燥保存。

反应信息

• 作为反应物：
  描述：

  4-(((吡啶-3-基甲氧基)羰基氨基)甲基)苯甲酸 在 草酰氯 、 N,N-二甲基甲酰胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 20.0h， 生成 恩替诺特
  参考文献：
  名称：

  Synthesis and Histone Deacetylase Inhibitory Activity of New Benzamide Derivatives

  摘要：

  Newly synthesized benzamide derivatives were evaluated for their inhibitory activity against histone deacetylase. The structure of these derivatives was unrelated to the known inhibitors, and IC50 values of the active compounds were in the range of 2-50 mu M. Structure-activity relationship on the benzanilide moiety showed that the 2'-substituent, an amino or hydroxy group, was indispensable for inhibitory activity. Although the electronic influence of the substituent in the anilide moiety showed only a small effect on inhibitory activity, the steric factor in the anilide moiety, especially at positions 3'and 4', played an important role in interaction with the enzyme. Among these benzamide derivatives, MS-275 (1), which showed significant antitumor activity in vivo, has been selected for further investigation.

  DOI：

  10.1021/jm980565u
• 作为产物：
  描述：

  3-吡啶甲醇 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 4-(((吡啶-3-基甲氧基)羰基氨基)甲基)苯甲酸
  参考文献：
  名称：

  Synthesis and Histone Deacetylase Inhibitory Activity of New Benzamide Derivatives

  摘要：

  Newly synthesized benzamide derivatives were evaluated for their inhibitory activity against histone deacetylase. The structure of these derivatives was unrelated to the known inhibitors, and IC50 values of the active compounds were in the range of 2-50 mu M. Structure-activity relationship on the benzanilide moiety showed that the 2'-substituent, an amino or hydroxy group, was indispensable for inhibitory activity. Although the electronic influence of the substituent in the anilide moiety showed only a small effect on inhibitory activity, the steric factor in the anilide moiety, especially at positions 3'and 4', played an important role in interaction with the enzyme. Among these benzamide derivatives, MS-275 (1), which showed significant antitumor activity in vivo, has been selected for further investigation.

  DOI：

  10.1021/jm980565u

文献信息

• Method of producing benzamide derivatives
  申请人：Mitsui Chemicals, Inc.

  公开号：US06320078B1

  公开（公告）日：2001-11-20

  In the case that a selectively monoacylated phenylenediamine derivative which is useful as any of medicines, agricultural chemicals, animal drugs and the intermediates of chemicals is prepared by reacting a benzoic acid derivative with a phenylenediamine derivative, the benzoic acid derivative is converted into a benzoyl imidazole derivative and this benzoyl imidazole derivative is then reaction with the phenylenediamine derivative, whereby the improvement of a preparation efficiency and the high selectivity of the monoacylation can be achieved, the steps of protection and deprotection being omitted.

  在一个选择性地单酰化的苯二胺衍生物的情况下，该衍生物作为药物、农药、兽药和化学品的中间体是有用的，通过将苯甲酸衍生物与苯二胺衍生物反应来制备，所述苯甲酸衍生物被转化为苯甲酰亚胺衍生物，然后这个苯甲酰亚胺衍生物再与苯二胺衍生物反应，通过这种方式可以实现在不进行保护和脱保护步骤的情况下提高制备效率和单酰化的高度选择性。
• [EN] INHIBITORS OF HISTONE DEACETYLASE<br/>[FR] INHIBITEURS D'HISTONE DEACETYLASE
  申请人：METHYLGENE INC

  公开号：WO2005030704A1

  公开（公告）日：2005-04-07

  The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.

  这项发明涉及抑制组蛋白去乙酰化酶。该发明提供了抑制组蛋白去乙酰化酶酶活性的化合物和方法。该发明还提供了治疗细胞增殖性疾病和症状的组合物和方法。
• Development of Potential Antitumor Agents. Synthesis and Biological Evaluation of a New Set of Sulfonamide Derivatives as Histone Deacetylase Inhibitors
  作者：Giliane Bouchain、Silvana Leit、Sylvie Frechette、Elie Abou Khalil、Rico Lavoie、Oscar Moradei、Soon Hyung Woo、Marielle Fournel、Pu T. Yan、Ann Kalita、Marie-Claude Trachy-Bourget、Carole Beaulieu、Zuomei Li、Marie-France Robert、A. Robert MacLeod、Jeffrey M. Besterman、Daniel Delorme

  DOI：10.1021/jm020377a

  日期：2003.2.1

  and anilides have been synthesized and studied as histone deacetylase (HDAC) inhibitors that can induce hyperacetylation of histones in human cancer cells. The inhibition of HDAC activity represents a novel approach for intervening in cell cycle regulation. The lead candidates were screened in a panel of human tumor and normal cell lines. They selectively inhibit proliferation, cause cell cycle blocks

  作为组蛋白脱乙酰基酶（HDAC）抑制剂，已经合成并研究了一系列磺酰胺异羟肟酸和苯甲酸酯，它们可以诱导人癌细胞中组蛋白的超乙酰化。HDAC活性的抑制代表一种干预细胞周期调控的新方法。在一组人类肿瘤和正常细胞系中筛选了主要候选药物。它们选择性抑制增殖，引起细胞周期阻滞，并诱导人癌细胞而非正常细胞凋亡。描述了结构活性关系，抗增殖活性和体内功效。
• [EN] ANTIMICROBIAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIMICROBIENS
  申请人：AKTHELIA PHARMACEUTICALS

  公开号：WO2015063694A1

  公开（公告）日：2015-05-07

  The invention provides compounds for use in treating microbial infection in an animal. Example compounds include Pyridin-3-ylmethyl (4-((2-aminophenyl)- carbamoyl)benzyl)carbamate ("Entinostat"). The compounds can act via induction of the innate antimicrobial peptide defense system, and stimulation of autophagy.

  这项发明提供了用于治疗动物微生物感染的化合物。示例化合物包括吡啶-3-基甲基(4-((2-氨基苯基)-羰胺)苄基)氨基甲酸酯（"Entinostat"）。这些化合物可以通过诱导天然抗微生物肽防御系统和促进自噬来发挥作用。
• Histone deacetylase inhibitors and uses thereof
  申请人：Li Jianqi

  公开号：US20110152323A1

  公开（公告）日：2011-06-23

  The present invention discloses a group of histone deacetylase inhibitors and use thereof. The histone deacetylase inhibitors are useful in the treatment of malignant tumors and the diseases associated with differentiation and proliferation. The histone deacetylase inhibitors are the compounds represented by the following formula or salts thereof:

  本发明公开了一组组蛋白去乙酰化酶抑制剂及其用途。这些组蛋白去乙酰化酶抑制剂在治疗恶性肿瘤和与分化和增殖相关的疾病中非常有用。这些组蛋白去乙酰化酶抑制剂是由以下式表示的化合物或其盐：