N-苯基乙酰基-对氨基苯甲酸 | 73548-12-6

• 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: N-苯基乙酰基-对氨基苯甲酸
• 中文别名: N-苯乙酰-P-氨基苯甲酸；4-[(苯乙酰基)氨基]苯甲酸
• 英文名称: 4-(2-phenylacetamido)benzoic acid
• 英文别名: 4-[(Phenylacetyl)amino]benzoic acid；4-[(2-phenylacetyl)amino]benzoic acid
• CAS: 73548-12-6
• 化学式: C₁₅H₁₃NO₃
• mdl: MFCD00056706
• 分子量: 255.273
• InChiKey: VNHSSBYXYMABJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-苯基乙酰基-对氨基苯甲酸 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 N-羟基-4-[(2-苯基乙酰基)氨基]苯甲酰胺
  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：

  methyl 4-(2-phenylacetamido)benzoate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.0h， 生成 N-苯基乙酰基-对氨基苯甲酸
  参考文献：
  名称：

  [EN] HDAC3-SELECTIVE INHIBITORS
  [FR] INHIBITEURS SÉLECTIFS DE HDAC3

  摘要：

  本文披露了选择性HDAC抑制剂。在某些实施例中，这些化合物是选择性HDAC3抑制剂。这些化合物可用于治疗各种疾病，包括癌症，如乳腺癌、虚弱和肝脂肪变性。

  公开号：

  WO2018223122A1

文献信息

• Design, synthesis, and activity evaluation of selective inhibitors of anti-apoptotic Bcl-2 proteins: The effects on the selectivity of the P1 pockets in the active sites
  作者：Mingping Wang、Wei Tian、Chongqing Wang、Shihai Lu、Chao Yang、Juan Wang、Yunlong Song、Youjun Zhou、Ju Zhu、Zhiyu Li、Canhui Zheng

  DOI：10.1016/j.bmcl.2016.09.061

  日期：2016.11

  The anti-apoptotic Bcl-2 proteins are attractive targets for anti-cancer drug development, and the discovery of their selective inhibitors has become a research focus. In this Letter, obvious differences in the P1 pocket of the active site between Bcl-2, Bcl-xL, and Mcl-1 proteins were proposed by the structural comparison of these proteins. As a result, the groups in their inhibitors binding to the P1

  抗凋亡的Bcl-2蛋白是抗癌药物开发的有吸引力的目标，其选择性抑制剂的发现已成为研究的重点。在这封信中，Bcl-2，Bcl-x L和Mcl-1蛋白在活性位点的P1口袋中存在明显差异，这是通过对这些蛋白的结构比较提出的。结果，其抑制剂中与P1口袋结合的基团可能对这些蛋白质的选择性产生重大影响。基于该假设，设计了前导化合物B-1的五种类型的衍生物，以及几种Bcl-x L（E-1）或Mcl-1蛋白（G） 被发现。本信中发现的Mcl-1蛋白选择性抑制剂为新型抗肿瘤药的开发提供了新的结构类型。
• Acylated 1<i>H</i>-1,2,4-Triazol-5-amines Targeting Human Coagulation Factor XIIa and Thrombin: Conventional and Microscale Synthesis, Anticoagulant Properties, and Mechanism of Action
  作者：Marvin Korff、Lukas Imberg、Jonas M. Will、Nico Bückreiß、Svetlana A. Kalinina、Benjamin M. Wenzel、Gregor A. Kastner、Constantin G. Daniliuc、Maximilian Barth、Ruzanna A. Ovsepyan、Kirill R. Butov、Hans-Ulrich Humpf、Matthias Lehr、Mikhail A. Panteleev、Antti Poso、Uwe Karst、Torsten Steinmetzer、Gerd Bendas、Dmitrii V. Kalinin

  DOI：10.1021/acs.jmedchem.0c01635

  日期：2020.11.12

  We herein report the conventional and microscale parallel synthesis of selective inhibitors of human blood coagulation factor XIIa and thrombin exhibiting a 1,2,4-triazol-5-amine scaffold. Structural variations of this scaffold allowed identifying derivative 21i, a potent 29 nM inhibitor of FXIIa, with improved selectivity over other tested serine proteases and also finding compound 21m with 27 nM

  我们在此报告了常规和微观并行合成的人类凝血因子XIIa和凝血酶的选择性抑制剂，这些抑制剂表现出1,2,4-三唑-5-胺骨架。该支架的结构变异允许鉴定衍生物21i（一种有效的FXIIa抑制剂29nM），具有比其他经过测试的丝氨酸蛋白酶更高的选择性，还可以发现化合物21m对凝血酶具有27 nM的抑制活性。首次证明酰化的1,2,4-三唑-5-胺具有抗凝特性，并具有影响凝血酶和癌细胞诱导的血小板凝集的能力。进行的质谱分析和分子建模使我们能够发现合成的抑制剂与FXIIa活性位点之间以前未知的相互作用，从而揭示了FXIIa抑制的机理细节。合成的化合物代表了开发新的抗血栓药物或化学工具以研究FXIIa和凝血酶在生理和病理过程中的作用的有希望的起点。
• [EN] HDAC3-SELECTIVE INHIBITORS<br/>[FR] INHIBITEURS SÉLECTIFS DE HDAC3
  申请人：OHIO STATE INNOVATION FOUNDATION

  公开号：WO2018223122A1

  公开（公告）日：2018-12-06

  Disclosed herein are selective HDAC inhibitors. In some embodiments, the compounds are selective HDAC3 inhibitors. The compounds are useful to treat a variety of conditions, including cancers, i.e., breast cancer, cachexia, and liver steatosis.

  本文披露了选择性HDAC抑制剂。在某些实施例中，这些化合物是选择性HDAC3抑制剂。这些化合物可用于治疗各种疾病，包括癌症，如乳腺癌、虚弱和肝脂肪变性。
• 4-[4-[(2-Hydroxybenzoyl)amino]phenyl]butyric Acid as a Novel Oral Delivery Agent for Recombinant Human Growth Hormone
  作者：Andrea Leone-Bay、Koc-Kan Ho、Rajesh Agarwal、Robert A. Baughman、Kiran Chaudhary、Frenel DeMorin、Lise Genoble、Campbell McInnes、Christine Lercara、Sam Milstein、Doris O'Toole、Donald Sarubbi、Bruce Variano、Duncan R. Paton

  DOI：10.1021/jm960038f

  日期：1996.1.1

  A series of N-acetylated, non-alpha, aromatic amino acids was prepared and shown to promote the absorption of recombinant human growth hormone (rhGH) from the gastrointestinal tract. Seventy compounds in this family were tested in vivo in rats. Of the compounds tested, 4-[4-[(2-hydroxybenzoyl)amino]phenyl]butyric acid was identified as a preclinical candidate and was used to demonstrate the oral delivery of rhGH in primates. A significant positive correlation was found between the relative log k' of the delivery agents, as determined by HPLC on an immobilized artificial membrane (IAM) column, and serum rhGH concentrations following oral or colonic dosing in rats. Structure-activity relationships have also been developed on the basis of electronic effects and hydrogen-bonding characteristics of the aromatic amide substituents.
• DE915214
  申请人：——

  公开号：——

  公开（公告）日：——