ethyl 2-(pyridin-3-yl)thiazole-4-carboxylate | 39067-28-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-(pyridin-3-yl)thiazole-4-carboxylate
• 英文别名: ethyl 2-pyridin-3-yl-1,3-thiazole-4-carboxylate
• CAS: 39067-28-2
• 化学式: C₁₁H₁₀N₂O₂S
• mdl: MFCD00052302
• 分子量: 234.279
• InChiKey: UXJLPDWBCGOLPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-(pyridin-3-yl)thiazole-4-carboxylate 在 草酰氯 、 N,N-二甲基甲酰胺 、 lithium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-(吡啶-3-基)噻唑-4-羰酰氯
  参考文献：
  名称：

  Discovery of Novel Aryl Carboxamide Derivatives as Hypoxia-Inducible Factor 1α Signaling Inhibitors with Potent Activities of Anticancer Metastasis

  摘要：

  In order to discover novel hypoxia-inducible factor 1 (HIF-1) inhibitors for the cancer metastasis treatment, 68 new aryl carboxamide compounds were synthesized and evaluated for their inhibitory effect by dual luciferase-reporter assay. Based on five rounds of investigation on structure-activity relationships step by step, compound 30m was discovered as the most active inhibitor (IC50 = 0.32 mu M) with no obvious cytotoxicity (CC50 > 50 mu M). It effectively attenuated hypoxia-induced HIF-1 alpha protein accumulation and reduced transcription of vascular epidermal growth factor in a dose-dependent manner, which was further demonstrated by its inhibitory potency on capillary-like tube formation, angiogenesis of zebrafish as well as cellular migration and invasion. Importantly, compound 30m exhibited antimetastatic potency in breast cancer lung metastasis in the mice model, indicating its promising therapeutic potential for prevention and treatment of tumor metastasis. These results definitely merit attention for further rational design of more efficient HIF-1 inhibitors in the future.

  DOI：

  10.1021/acs.jmedchem.9b01313
• 作为产物：
  描述：

  巯基尼古胺 、 2-丁酮酸乙酯 以 乙醇 为溶剂， 反应 6.0h， 以73%的产率得到ethyl 2-(pyridin-3-yl)thiazole-4-carboxylate
  参考文献：
  名称：

  Discovery of Novel Aryl Carboxamide Derivatives as Hypoxia-Inducible Factor 1α Signaling Inhibitors with Potent Activities of Anticancer Metastasis

  摘要：

  In order to discover novel hypoxia-inducible factor 1 (HIF-1) inhibitors for the cancer metastasis treatment, 68 new aryl carboxamide compounds were synthesized and evaluated for their inhibitory effect by dual luciferase-reporter assay. Based on five rounds of investigation on structure-activity relationships step by step, compound 30m was discovered as the most active inhibitor (IC50 = 0.32 mu M) with no obvious cytotoxicity (CC50 > 50 mu M). It effectively attenuated hypoxia-induced HIF-1 alpha protein accumulation and reduced transcription of vascular epidermal growth factor in a dose-dependent manner, which was further demonstrated by its inhibitory potency on capillary-like tube formation, angiogenesis of zebrafish as well as cellular migration and invasion. Importantly, compound 30m exhibited antimetastatic potency in breast cancer lung metastasis in the mice model, indicating its promising therapeutic potential for prevention and treatment of tumor metastasis. These results definitely merit attention for further rational design of more efficient HIF-1 inhibitors in the future.

  DOI：

  10.1021/acs.jmedchem.9b01313

文献信息

• HIV protease inhibiting compounds
  申请人：DeGoey A. David

  公开号：US20050131017A1

  公开（公告）日：2005-06-16

  A compound of the formula is disclosed as an HIV protease inhibitor. Methods and compositions for inhibiting an HIV infection are also disclosed.

  公开了一种公式的化合物作为HIV蛋白酶抑制剂。还公开了用于抑制HIV感染的方法和组合物。
• Lactol PAF antagonists
  申请人：British Biotech Pharmaceuticals Limited

  公开号：US05428168A1

  公开（公告）日：1995-06-27

  The invention encompasses compounds of general formula I: ##STR1## wherein W represents an imidazo[4,5-c]pyridyl group, optionally substituted with one or more substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halo, CF, and CN; and Z, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 are variables. These compounds are useful as antagonists of platelet activating factor.

  这项发明涵盖了一般式I的化合物：##STR1## 其中W代表一种咪唑并[4,5-c]吡啶基团，可选地取代为一个或多个从C.sub.1 -C.sub.6烷基，C.sub.1 -C.sub.6烷氧基，卤素，CF和CN中选择的取代基；而Z，R.sup.1，R.sup.2，R.sup.3，R.sup.4，R.sup.5，R.sup.6是变量。这些化合物可用作血小板活化因子的拮抗剂。
• [EN] QUINOLINE DERIVATIVES AS TAM RTK INHIBITORS<br/>[FR] DÉRIVÉS DE QUINOLÉINE UTILISÉS COMME INHIBITEURS DE RTK DE TAM
  申请人：QURIENT CO LTD

  公开号：WO2016166250A1

  公开（公告）日：2016-10-20

  The present invention relates to novel compounds which are inhibitors of TAM (Axl, Mer and Tyro 3) and/or Met family receptor tyrosine kinases (RTKs). These compounds are suitable for the treatment of disorders associated with, accompanied by, caused by or induced by a receptor of the TAM family, in particular a hyperfunction thereof. The compounds are suitable for the treatment of hyperproliferative disorders, such as cancer, particularly immune-suppressive cancer, refractory cancer and cancer metastases.

  本发明涉及一种新型化合物，它们是TAM（Axl、Mer和Tyro 3）和/或Met家族受体酪氨酸激酶（RTKs）的抑制剂。这些化合物适用于治疗与TAM家族受体相关的、伴随的、由其引起的或诱导的疾病，特别是其过度功能。这些化合物适用于治疗高增殖性疾病，如癌症，特别是免疫抑制性癌症、难治性癌症和癌症转移。
• Novel Heterocyclic Compounds as Pesticides
  申请人：MÜHLTHAU Friedrich August

  公开号：US20120094837A1

  公开（公告）日：2012-04-19

  The present invention relates to novel heterocyclic compounds, to processes for preparation thereof and to the use thereof for controlling animal pests, which include arthropods and especially insects.

  本发明涉及新颖的杂环化合物，其制备过程以及用于控制动物害虫的用途，包括节肢动物，尤其是昆虫。
• Synthesis of the Central Heterocyclic Skeleton of an Antibiotic, A10255
  作者：Kazuyuki Umemura、Shin Ikeda、Juji Yoshimura、Kazuo Okumura、Hiroyuki Saito、Chung-gi Shin

  DOI：10.1246/cl.1997.1203

  日期：1997.12

  The central heterocylic skeleton (13) of an antibiotic, A10255, was synthesized by stepwise introduction of two groups into the 2,6-positions of 3-(4-ethoxycarbonyl)-2-thiazolyl} pyridine, via 17 steps in 4.8% total yield.

  在 3-（4-乙氧羰基）-2-噻唑基}吡啶的 2,6 位逐步引入两个基团，通过 17 个步骤合成了抗生素 A10255 的中心杂环骨架（13），总产率为 4.8%。