4-(丁基氨基)苯甲酸 | 99855-49-9

• 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-(丁基氨基)苯甲酸
• 中文别名: 4-丁酰氨基苯甲酸
• 英文名称: 4-butyrylamino-benzoic acid
• 英文别名: p-butanamidobenzoic acid；4-(Butyrylamino)benzoic acid；4-(butanoylamino)benzoic acid
• CAS: 99855-49-9
• 化学式: C₁₁H₁₃NO₃
• mdl: MFCD00448229
• 分子量: 207.229
• InChiKey: MUILCOCVGKGNRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  4-(丁基氨基)苯甲酸 在 palladium on activated charcoal TEA 、 氢气 、 双(2-氧代-3-恶唑烷基)次磷酰氯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 4-butyrylamino-N-hydroxy-benzamide
  参考文献：
  名称：

  Zn²⁺-Chelating Motif-Tethered Short-Chain Fatty Acids as a Novel Class of Histone Deacetylase Inhibitors

  摘要：

  Among various classes of histone deacetylase (HDAC) inhibitors, short-chain fatty acids exhibit the least potency, with IC50 in the millimolar range. We rationalized that this weak potency was, in part, attributable to their inability to access the zinc cation in the HDAC active-site pocket, which is pivotal to the deacetylation catalysis. We thus explored the structural optimization of valproate, butyrate, phenylacetate, and phenylbutyrate by coupling them with Zn2+-chelating motifs (hydroxamic acid and o-phenylenediamine) through aromatic W-amino acid linkers. This strategy has led to a novel class of Zn2+ -chelating, motif-tethered, short-chain fatty acids that exhibited varying degrees of HDAC inhibitory potency. One hydroxamate-tethered phenylbutyrate compound, N-hydroxy-4-(4-phenylbutyrylamino)benzamide (HTPB), displayed nanomolar potency in inhibiting HDAC activity. Exposure of several cancer cell lines to HTPB at the submicromolar level showed reduced cell proliferation accompanied by histone hyperacetylation and elevated p21(WAF/CIPI) expression, which are hallmark features associated with intracellular HDAC inhibition.

  DOI：

  10.1021/jm0303655
• 作为产物：
  描述：

  4-氨基苯甲酸甲酯 在 氢氧化钾 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 4-(丁基氨基)苯甲酸
  参考文献：
  名称：

  Zn²⁺-Chelating Motif-Tethered Short-Chain Fatty Acids as a Novel Class of Histone Deacetylase Inhibitors

  摘要：

  Among various classes of histone deacetylase (HDAC) inhibitors, short-chain fatty acids exhibit the least potency, with IC50 in the millimolar range. We rationalized that this weak potency was, in part, attributable to their inability to access the zinc cation in the HDAC active-site pocket, which is pivotal to the deacetylation catalysis. We thus explored the structural optimization of valproate, butyrate, phenylacetate, and phenylbutyrate by coupling them with Zn2+-chelating motifs (hydroxamic acid and o-phenylenediamine) through aromatic W-amino acid linkers. This strategy has led to a novel class of Zn2+ -chelating, motif-tethered, short-chain fatty acids that exhibited varying degrees of HDAC inhibitory potency. One hydroxamate-tethered phenylbutyrate compound, N-hydroxy-4-(4-phenylbutyrylamino)benzamide (HTPB), displayed nanomolar potency in inhibiting HDAC activity. Exposure of several cancer cell lines to HTPB at the submicromolar level showed reduced cell proliferation accompanied by histone hyperacetylation and elevated p21(WAF/CIPI) expression, which are hallmark features associated with intracellular HDAC inhibition.

  DOI：

  10.1021/jm0303655

文献信息

• Prodrugs of butyric acid. Novel derivatives possessing increased aqueous solubility and potential for treating cancer and blood diseases
  作者：A Nudelman

  DOI：10.1016/s0223-5234(00)01199-5

  日期：2001.1

  The synthesis and biological activities of acidic, basic and neutral types of butyric acid (BA) prodrugs possessing increased aqueous solubility are described. The compounds are butyroyloxyalkyl derivatives of carboxylic acids, which possess functionalities suitable for aqueous solubilization. The anticancer activity of the prodrugs in vitro was evaluated by examining their effect on the growth of

  描述了具有增加的水溶性的酸性，碱性和中性类型的丁酸（BA）前药的合成和生物活性。该化合物是羧酸的丁酰氧基烷基衍生物，其具有适合于水溶性溶解的官能度。通过检查前药对人结肠癌，乳腺癌和胰腺癌细胞系生长的影响来评估前药的体外抗癌活性，并确定其在水介质中的溶解度。就活性和溶解度而言，最有前途的化合物被发现是戊二酸2a和烟酸4a的丁酰氧基甲基酯和磷酸作为其二乙酯10a的磷酸，其IC（50）值等于或小于100 microM。预期这些前药在代谢水解后会释放甲醛。代谢时释放乙醛的相应丁酰氧基乙基酯（2b，4b和10b）的效力明显较低。在人类前列腺癌细胞系PC-3和LnCap的生长抑制以及在人类髓样白血病细胞系HL-60的诱导分化和凋亡中观察到相似的相关性。当测量人红白血病细胞系K562中血红蛋白（Hb）合成的诱导时，进一步证实了释放甲醛的前药2a和10a具有更高的生物活性。此外，治疗指数（IC（50）/
• [EN] SUBSTITUTED 6-CYCLOHEXYLALKYL SUBSTITUTED 2-QUINOLINONES AND 2-QUINOXALINONES AS POLY(ADP-RIBOSE) POLYMERASE INHIBITORS<br/>[FR] 2-QUINOLINONES SUBSTITUES 6-CYCLOHEXYLALKYL SUBSTITUES ET 2-QUINOXALINONES UTILISES EN TANT QU'INHIBITEURS DE LA POLY(ADP-RIBOSE) POLYMERASE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2005058843A1

  公开（公告）日：2005-06-30

  The present invention provides compounds of formula (I), their use as PARP inhibitors as well as pharmaceutical compositions comprising said compounds of formula (I) wherein n, s, R1, R2, R3, Q, X and Y have defined meanings.

  本发明提供了式(I)的化合物，其作为PARP抑制剂的用途，以及包含所述式(I)的化合物的药物组合物，其中n、s、R1、R2、R3、Q、X和Y具有定义的含义。
• [EN] QUINAZOLINONE DERIVATIVES AS PARP INHIBITORS<br/>[FR] DERIVES DE QUINAZOLINONE EN TANT QU'INHIBITEURS DE PARP
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2006003146A1

  公开（公告）日：2006-01-12

  The present invention provides compounds of formula (I), their use as PARP inhibitors as well as pharmaceutical compositions comprising said compounds of formula (I) wherein R1, R2, R3, L, X, Y and Z have defined meanings.

  本发明提供了式(I)的化合物，它们可用作PARP抑制剂，以及包含该式(I)化合物的制药组合物，其中R1、R2、R3、L、X、Y和Z具有定义的含义。
• QUINOLONE DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF
  申请人：KOGA Yuji

  公开号：US20120136025A1

  公开（公告）日：2012-05-31

  Disclosed are quinolone derivatives characterized in that these have lower alkyl, cycloalkyl or the like at the 1-position; —N(R 0 )C(O)-lower alkylene-CO 2 R 0 , lower alkylene-CO 2 R 0 , lower alkenylene-CO 2 R 0 , —O-lower alkylene-CO 2 R 0 , —O-(lower alkylene which may be substituted with —CO 2 R 0 )-aryl or —O-lower alkenylene-CO 2 R 0 (wherein R 0 is H or lower alkyl) at the 3-position; halogen at the 6-position; and amino group substituted with a substituent group having a ring structure at the 7-position, respectively, or pharmaceutically acceptable salts thereof, has excellent P2Y12 inhibitory activity. The quinolone derivatives have excellent platelet aggregation inhibitory activity. A method of using the compounds is also disclosed.

  本发明涉及喹诺酮衍生物，其特征在于它们在1-位具有较低烷基、环烷基或类似物；在3-位具有-N(R0)C(O)-较低烷基烯基-CO2R0、较低烷基-CO2R0、较低烯基-CO2R0、-O-较低烷基-CO2R0、-O-（可能被取代为-CO2R0的较低烷基）芳基或-O-较低烯基-CO2R0（其中R0为H或较低烷基）；在6-位具有卤素；在7-位具有被环状取代基取代的氨基，或其药学上可接受的盐，具有出色的P2Y12抑制活性。这些喹诺酮衍生物具有优异的血小板聚集抑制活性。本发明还公开了一种使用这些化合物的方法。
• Quinazolinone derivatives as PARP inhibitors
  申请人：Janssen Pharmaceutica NV

  公开号：US10150757B2

  公开（公告）日：2018-12-11

  The present invention provides compounds of formula (I), their use as PARP inhibitors as well as pharmaceutical compositions comprising said compounds of formula (I) wherein R1, R2, R3, L, X, Y and Z have defined meanings.

  本发明提供了式 (I) 化合物、其作为 PARP 抑制剂的用途以及包含所述式 (I) 化合物的药物组合物 其中 R1、R2、R3、L、X、Y 和 Z 具有定义的含义。