ethyl 2-[2-(benzoylamino)-1,3-thiazol-4-yl]acetate | 301226-58-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-[2-(benzoylamino)-1,3-thiazol-4-yl]acetate
• 英文别名: Ethyl 2-(2-benzamido-1,3-thiazol-4-yl)acetate
• CAS: 301226-58-4
• 化学式: C₁₄H₁₄N₂O₃S
• mdl: MFCD00751086
• 分子量: 290.343
• InChiKey: FSCXMDIXYSNIOD-UHFFFAOYSA-N

物化性质

• 熔点：
  92-95 °C
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  96.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-[2-(benzoylamino)-1,3-thiazol-4-yl]acetate 在 Oxone 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成 ethyl 2-(2-(benzoylimino)-3-hydroxy-2,3-dihydrothiazol-4-yl)acetate
  参考文献：
  名称：

  [EN] COMPOUNDS INHIBITORS OF ENZYME LACTATE DEHYDROGENASE (LDH) AND PHARMACEUTICAL COMPOSITIONS CONTAINING THESE COMPOUNDS
  [FR] COMPOSÉS INHIBITEURS D'ENZYME LACTATE DÉSHYDROGÉNASE (LDH) ET COMPOSITIONS PHARMACEUTIQUES CONTENANT CES COMPOSÉS

  摘要：

  这项发明涉及化合物，其中一些是新颖的，以及它们的药用应用。该发明的化合物抑制乳酸脱氢酶（LDH）酶，该酶参与低氧肿瘤细胞的代谢过程，以及疟疾引起的寄生原虫利用获取所需大部分能量的过程。

  公开号：

  WO2011054525A1
• 作为产物：
  描述：

  2-氨基-4-噻唑乙酸乙酯 、 苯甲酰氯 在 吡啶 作用下， 以60%的产率得到ethyl 2-[2-(benzoylamino)-1,3-thiazol-4-yl]acetate
  参考文献：
  名称：

  具有抗血小板活性的新型 2-氨基-噻唑-4-乙酰胺

  摘要：

  在 Born 试验中，合成了 23 种标题化合物，并研究了它们对作为聚集诱导剂的胶原蛋白、ADP、肾上腺素和血小板激活因子 (PAF) 的抗血小板活性。使用胶原蛋白，发现了三种 IC50 值低于 10 μM 的化合物（3a、3b、3c），并确定了 15 种 IC50 值在 10 到 100 μM 之间的化合物。一般来说，环己氨基位于 4-甲酰胺部分是这种药理活性的先决条件。观察到结构元素 Y 中取代基 R1 的明显依赖性。4-甲酰胺取代基中的间隔n也是如此。化合物 3e 显示出强烈的 ADP 拮抗作用（IC50 = 2.2 nM）；3c 拮抗肾上腺素 (IC50 = 2.8 nM)，而 3n 对血小板激活因子非常有效 (IC50 = 0.2 μM)。

  DOI：

  10.1002/ardp.200700046

文献信息

• Synthesis, in vitro and in silico studies of novel potent urease inhibitors: N -[4-({5-[(3-Un/substituted-anilino-3-oxopropyl)sulfanyl]-1,3,4-oxadiazol-2-yl}methyl)-1,3-thiazol-2-yl]benzamides
  作者：Muhammad Athar Abbasi、Mubashir Hassan、Aziz-ur-Rehman、Sabahat Zahra Siddiqui、Hussain Raza、Syed Adnan Ali Shah、Sung-Yum Seo

  DOI：10.1016/j.bmc.2018.06.005

  日期：2018.7

  The present article describes the synthesis, in vitro urease inhibition and in silico molecular docking studies of a novel series of bi-heterocyclic bi-amides. The synthesis of title compounds was initiated by benzoylation, with benzoyl chloride (1), of the key starter ethyl 2-(2-amino-1,3-thiazol-4-yl)acetate (2) in weak basic aqueous medium followed by hydrazide formation, 4, and cyclization with

  本文介绍了一系列新型的双杂环双酰胺的合成，体外脲酶抑制和计算机分子对接研究。标题化合物的合成是通过在弱碱性水性介质中，将关键起始剂2-（2-氨基-1,3-噻唑-4-基）乙酸乙酯（2）与苯甲酰氯（1）进行苯甲酰化反应开始的，然后酰肼的形成4，并与CS2环化以形成母体双杂环亲核试剂N- 4-[（5-硫烷基-1,3,4-恶二唑-2-基）甲基] -1,3-噻唑- 2-基}苯甲酰胺（5）。通过两步法合成了各种亲电试剂8a-1，最后将它们与5偶联，得到了目标双杂环双酰胺分子9a-1。通过IR，1 H NMR，13 C NMR，EI-MS和元素分析证实了新合成产物的结构。这些分子对脲酶的体外筛选研究表明，大多数化合物均显示出对该酶的有效抑制潜力。相对于IC50值为21.11±0.12 µM的标准硫脲，化合物9j的IC50值为2.58±0.02 µM，显示出最有希望的抑制活性。在计算机研究中，充分增强了
• Discovery of novel dual inhibitors of VEGFR and PI3K kinases containing 2-ureidothiazole scaffold
  作者：Lin Li、Cun-Long Zhang、Hong-Rui Song、Chun-Yan Tan、Huai-Wei Ding、Yu-Yang Jiang

  DOI：10.1016/j.cclet.2015.09.008

  日期：2016.1

  2-ureidothiazole scaffold were designed and synthesized. Some compounds demonstrated inhibition of cell proliferation against both MDA-MB-231 and HepG2 cell lines using Sorafenib as the positive control. Compounds 6i showed a good to moderate inhibition on VEGFR-2 and PI3Kα which was proved by further molecular docking study. This study suggests that compound 6i is a potential dual inhibitor of VEGFR-2 and

  设计并合成了一系列具有2-（3-苯基）脲基噻唑-4-甲酰胺衍生物和2-脲基噻唑骨架的化合物。使用索拉非尼作为阳性对照，某些化合物显示出针对MDA-MB-231和HepG2细胞系的细胞增殖抑制作用。化合物6i对VEGFR-2和PI3Kα表现出良好至中度的抑制作用，这已通过进一步的分子对接研究得到证实。这项研究表明化合物6i是VEGFR-2和PI3Kα的潜在双重抑制剂，可用于进一步研究。
• Synthesis and biological evaluation of thiazole derivatives on basic defects underlying cystic fibrosis
  作者：Emanuela Pesce、Nicoletta Pedemonte、Alberto Leoni、Alessandra Locatelli、Rita Morigi

  DOI：10.1016/j.bmcl.2020.127473

  日期：2020.11

  Cystic fibrosis is a genetic disease caused by loss-of-function mutations in the cystic fibrosis transmembrane conductance regulator gene, encoding for CFTR protein. The most frequent mutation is the deletion of phenylalanine at position 508 (F508del), which leads to distinct defects in channel gating and cellular processing. In last years, several thiazole containing small molecules, endowed with dual F508del-CFTR modulator activity, proved to be able to target these defects. In search of new chemical entities able to restore CFTR function, we designed and synthesized a small series of sixteen thiazole derivatives. The designed compounds were studied as correctors and potentiators of F508del-CFTR. Although none of the molecules showed significant corrector activity, compounds 10 and 11 exhibited potentiator effects, thus allowing to determine some basic structural features which enable to obtain F508del-CFTR potentiator activity. In silico ADME studies showed that these derivatives obey Lipinski's rule of five and are expected to be orally bioavailable. Therefore, these molecules may represent a good starting point for the design of analogues endowed with improved CFTR potentiator activity and a good pharmacokinetic profile.
• Synthesis of novel N-(1,3-thiazol-2-yl)benzamide clubbed oxadiazole scaffolds: Urease inhibition, Lipinski rule and molecular docking analyses
  作者：Muhammad Athar Abbasi、Hussain Raza、Aziz-ur-Rehman、Sabahat Zahra Siddiqui、Syed Adnan Ali Shah、Mubashir Hassan、Sung-Yum Seo

  DOI：10.1016/j.bioorg.2018.10.018

  日期：2019.3

  Present work aimed to synthesize some unique bi-heterocyclic benzamides as lead compounds for the in vitro inhibition of urease enzyme, followed by in silico studies. These targeted benzamides were synthesized in good yields through a multi-step protocol and their structures were confirmed by IR, H-1 NMR, C-13 NMR, EI-MS and elemental analysis. The in vitro screening results showed that most of the ligands exhibited good inhibitory potentials against the urease. Chemo-informatics analysis envisaged that all these compounds obeyed the Lipinski's rule. Molecular docking results showed that 7h exhibited good binding energy value (- 8.40 kcal/mol) and was bound within the active region of urease enzyme. From the present investigation, it was inferred that some of these potent urease inhibitors might serve as novel templates in drug designing.
• KR2020/140099
  申请人：——

  公开号：——

  公开（公告）日：——