4-[(4-甲氧基苯甲酰基)氨基]苯甲酸乙酯 | 100278-51-1

• 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-[(4-甲氧基苯甲酰基)氨基]苯甲酸乙酯
• 英文名称: ethyl 4-(4-methoxybenzoylamino)benzoate
• 英文别名: ethyl 4-(4-methoxybenzamido)benzoate；Ethyl 4-[(4-methoxybenzoyl)amino]benzoate
• CAS: 100278-51-1
• 化学式: C₁₇H₁₇NO₄
• mdl: MFCD00406454
• 分子量: 299.326
• InChiKey: LMFLTKIABAVKNV-UHFFFAOYSA-N

物化性质

• 熔点：
  175 °C
• 沸点：
  388.5±27.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  4-[(4-甲氧基苯甲酰基)氨基]苯甲酸乙酯 在 草酰氯 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 4-(4-methoxybenzamido)benzoyl chloride
  参考文献：
  名称：

  Design, synthesis and insulin-sensitising effects of novel PTP1B inhibitors

  摘要：

  Fifteen novel sulfathiazole-related compounds were designed as PTP1B inhibitors based on a previously reported allosteric inhibitor (1) of PTP1B. These compounds were synthesized and evaluated against human recombinant PTP1B. Six compounds (3, 4, 8 and 14-16) exhibited significant inhibitory activity against PTP1B. The most active compound (16) showed IC50 value of 3.2 mu M and kinetic analysis indicated that it is a non-competitive inhibitor of PTP1B. Furthermore, compound 16 demonstrated excellent selectivity to PTP1B over other PTPs. It also displayed in vivo insulin sensitizing effect in the insulin resistant mice. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.073
• 作为产物：
  描述：

  大茴香酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 4-[(4-甲氧基苯甲酰基)氨基]苯甲酸乙酯
  参考文献：
  名称：

  Design, synthesis and insulin-sensitising effects of novel PTP1B inhibitors

  摘要：

  Fifteen novel sulfathiazole-related compounds were designed as PTP1B inhibitors based on a previously reported allosteric inhibitor (1) of PTP1B. These compounds were synthesized and evaluated against human recombinant PTP1B. Six compounds (3, 4, 8 and 14-16) exhibited significant inhibitory activity against PTP1B. The most active compound (16) showed IC50 value of 3.2 mu M and kinetic analysis indicated that it is a non-competitive inhibitor of PTP1B. Furthermore, compound 16 demonstrated excellent selectivity to PTP1B over other PTPs. It also displayed in vivo insulin sensitizing effect in the insulin resistant mice. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.073

文献信息

• Synthesis, characterisation and biological activity of novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds
  作者：Ş.Güniz Küçükgüzel、E.Elçin Oruç、Sevim Rollas、Fikrettin Şahin、Ahmet Özbek

  DOI：10.1016/s0223-5234(01)01326-5

  日期：2002.3

  4-thiazolidinone derivatives, namely 2-substituted-3-([4-(4-methoxybenzoylamino)benzoyl]amino)-4-thiazolidinones (7a-e) and 2-[4-(4-methoxybenzoylamino)benzoylhydrazono]-3-alkyl-4-thiazolidinones (5a-c) together with 2-[4-(4-methoxybenzoylamino)phenyl]-5-(substituted phenyl)amino-1,3,4-oxadiazoles (6a-c) have been synthesised as title compounds. N(1)-[4-(4-methoxybenzoylamino)benzoyl]-N(2)-substituted methylene

  2-噻唑烷酮衍生物的两个新颖系列，即2-取代的-3-（[[4-（4-甲氧基苯甲酰基氨基）苯甲酰基]氨基）-4-噻唑烷酮（7a-e）和2- [4-（4-甲氧基苯甲酰基氨基）苯甲酰肼基] -3-烷基-4-噻唑烷酮（5a-c）与2- [4-（4-甲氧基苯甲酰基氨基）苯基] -5-（取代的苯基）氨基-1,3,4-恶二唑（6a-c）具有合成为标题化合物。N（1）-[4-（4-甲氧基苯甲酰基氨基）苯甲酰基] -N（2）取代的亚甲基肼（3a-e）和1- [4-（4-甲氧基苯甲酰基氨基）苯甲酰基] -4-取代的苯基硫代氨基脲（4a -f）也被制备并用作中间体以得到标题化合物。筛选所有合成的化合物对结核分枝杆菌H37Rv的抗分枝杆菌活性以及对各种细菌和真菌的抗菌活性。发现化合物7a和7b是最具活性的衍生物，分别在6.25微克mL（-1）的初步筛选中显示出90％和98％的结核分枝杆菌H37Rv分枝杆菌生长抑制。但是，II级分析显示MIC值不小于6
• Type IIA - Type IIB protein tyrosine kinase inhibitors hybridization as an efficient approach for potent multikinase inhibitor development: Design, synthesis, anti-proliferative activity, multikinase inhibitory activity and molecular modeling of novel indolinone-based ureides and amides
  作者：Wagdy M. Eldehna、Ahmed M. El Kerdawy、Ghada H. Al-Ansary、Sara T. Al-Rashood、Mamdouh M. Ali、Abeer E. Mahmoud

  DOI：10.1016/j.ejmech.2018.11.061

  日期：2019.2

  potent derivative towards HepG2 cells (IC50 = 2.67 ± 0.14 μM), 6r stood out as the most potent indolinone against A498 cells (IC50 = 0.78 ± 0.02 μM). Additionally, the target indolinones displayed non-significant cytotoxic impact towards human normal melanocyte (HFB4). ADME prediction study of the designed compounds showed that they are not only with promising multikinase inhibitory activity but also

  基于我们对开发新型多激酶抑制剂的努力，在此我们报告了新型基于2-吲哚满酮的酰脲6a-u和酰胺10a - j的设计和合成。在这项工作中，我们采用IIA型PTK抑制剂（索拉非尼）和IIB型PTK抑制剂（舒尼替尼和nintedanib）之间的杂交策略。这是通过以下方式实现的舒尼替尼和nintedanib中的吲哚酮核心之间的连接非常合适，而索拉非尼中的茚满酮核心适合于激酶结构域前裂的铰链区和联芳基脲延伸区，而索拉非尼则位于门区域和疏水性后袋中。按照计划，设计的杂合化合物在VEGFR-2和FGFR-1活性位点上的分子对接揭示了它们建立由原始IIA型和IIB型抑制剂实现的结合相互作用的能力。评价所设计的化合物对VEGFR-2，PDGFR-b和FGFR-1的多激酶抑制活性以及对HepG2，MCF-7，A549和A498癌细胞系的抗增殖活性。脲基类似物6u成为具有VEGFR-2，FGFR-1和PDGFR-b
• Buchwald–Hartwig cross-coupling of amides (transamidation) by selective N–C(O) cleavage mediated by air- and moisture-stable [Pd(NHC)(allyl)Cl] precatalysts: catalyst evaluation and mechanism
  作者：Guangchen Li、Tongliang Zhou、Albert Poater、Luigi Cavallo、Steven P. Nolan、Michal Szostak

  DOI：10.1039/c9cy02080b

  日期：——

  The Pd–NHC-catalyzed acyl-type Buchwald–Hartwig cross-coupling of amides by N–C(O) cleavage (transamidation) provides a valuable alternative to the classical methods for amide synthesis. Herein, we report a combined experimental and computational study of the Buchwald–Hartwig cross-coupling of amides using well-defined, air- and moisture-stable [Pd(NHC)(allyl)Cl] precatalysts. Most crucially, we present

  通过N-C（O）裂解（酰胺基转移），Pd-NHC催化的酰胺基酰基型布赫瓦尔德-哈特维格交叉偶联为经典的酰胺合成方法提供了有价值的替代方法。本文中，我们报告了使用定义明确的，对空气和水分稳定的[Pd（NHC）（烯丙基）Cl]预催化剂进行的Buchwald-Hartwig酰胺交叉偶联的实验和计算研究。最关键的是，我们对一系列不同的Pd（II）-NHC预催化剂进行了全面评估，这些催化剂具有不同的NHC支架和可抛弃的配体，用于合成与化学计量无过渡金属的酰胺化方法不兼容的官能化酰胺。此外，我们目前通过DFT方法对一系列不同的Pd（II）的催化循环进行评估）– NHC预催化剂。获得NHC支持的酰基-钯（II）酰胺基配合物的可行性将对涉及稳定酰胺亲电试剂的交叉偶联方法的设计和开发产生影响。
• Design, synthesis, and activity evaluation of broad-spectrum small-molecule inhibitors of anti-apoptotic Bcl-2 family proteins: Characteristics of broad-spectrum protein binding and its effects on anti-tumor activity
  作者：Can-Hui Zheng、Hui Yang、Meng Zhang、Shi-Hai Lu、Duo Shi、Juan Wang、Xiu-Hua Chen、Xiao-Hui Ren、Jia Liu、Jia-Guo Lv、Ju Zhu、You-Jun Zhou

  DOI：10.1016/j.bmcl.2011.11.101

  日期：2012.1

  than ABT-737 at inhibiting growth in multiple tumor cell lines known to express Bcl-xL, Bcl-2, and Mcl-1 proteins at high levels. Compounds B-11 and B-12 had the strongest anti-tumor activity of any compounds we produced. This study suggests that it is feasible to design small-molecule inhibitors based on the structure of Bim BH3, which shows broad-spectrum binding to Bcl-xL, Bcl-2, and Mcl-1 proteins

  在比较Bim BH3：Bcl-x L络合物和ABT-737：Bcl-x L络合物的结构的基础上，设计了一系列A类化合物。这些化合物具有ABT-737的基本骨架和Bim BH3的h2残基。在饱和诱变测定中，这些残基已显示出与Bim BH3的广谱结合特性有关。与作为Bcl-2蛋白家族抗凋亡成员的选择性抑制剂的ABT-737不同，A类化合物对目标蛋白具有广谱结合活性，类似于Bim BH3肽。然后通过修饰最有效的A类化合物的结构来合成B类化合物化合物A - 4。这些大多数B类化合物显示出比A类化合物更好的与靶蛋白的结合亲和力。他们还显示出比ABT-737更有效地抑制已知以高水平表达Bcl-x L，Bcl-2和Mcl-1蛋白的多种肿瘤细胞的生长。在我们生产的所有化合物中，化合物B - 11和B - 12具有最强的抗肿瘤活性。这项研究表明，根据Bim BH3的结构设计小分子抑制剂是可行的，该结构显示了与Bcl-x
• Synthesis and Biological Evaluation of Some Hydrazide-Hydrazone Derivatives as Anticancer Agents
  作者：Kadriye Akdağ、Fatih Tok、Sevgi Karakuş、Ömer Erdoğan、Özge Çevik、Bedia Kaymakçıoğlu

  DOI：10.17344/acsi.2022.7614

  日期：——

  In this study, a series of hydrazide-hydrazone derivatives (3a-3u) were synthesized and evaluated for their anticancer activitiesagainst prostate cancer cell line (PC-3), breast cancer cell line (MCF-7), colon cancer cell line (HT-29) and human umbilical vein endothelial cells (HUVEC) using MTT assay. In particular, compound 3h having a pyrrole ring was found to be the most potent derivative with IC50 = 1.32, 2.99, 1.71 μM against PC-3, MCF-7, HT-29 cancer cell lines respectively using paclitaxel as a standard compound. Furthermore, compound 3h was subjected to further biological studies such as caspase-3 activity and Annexin-V assay to evaluate their inhibitory potentials. The activity results displayed that compound 3h increased caspase-3 activation and the number of cells to early apoptosis. The additional studies like pharmacokinetics, bioavailability scores and drug-likeness properties were also evaluated. The in silico pharmacokinetics predictions displayed that the bioavailability of these compounds may be high.

  本研究合成了一系列酰肼-腙衍生物（3a-3u），并使用 MTT 法评估了它们对前列腺癌细胞系（PC-3）、乳腺癌细胞系（MCF-7）、结肠癌细胞系（HT-29）和人脐静脉内皮细胞（HUVEC）的抗癌活性。其中，以紫杉醇为标准化合物，发现具有吡咯环的化合物 3h 是最有效的衍生物，对 PC-3、MCF-7 和 HT-29 癌细胞株的 IC50 分别为 1.32、2.99 和 1.71 μM。此外，还对化合物 3h 进行了进一步的生物学研究，如 Caspase-3 活性和 Annexin-V 检测，以评估其抑制潜力。活性结果显示，化合物 3h 增加了 caspase-3 的活化和早期凋亡细胞的数量。此外，还评估了药代动力学、生物利用度评分和药物相似性等其他研究。硅药代动力学预测显示，这些化合物的生物利用度可能很高。