ethyl 3'-chlorooxanilate | 17710-00-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 3'-chlorooxanilate
• 英文别名: ethyl 2-(3-chloroanilino)-2-oxoacetate
• CAS: 17710-00-8
• 化学式: C₁₀H₁₀ClNO₃
• mdl: MFCD01806306
• 分子量: 227.647
• InChiKey: ROIXZGUCSLCCRW-UHFFFAOYSA-N

物化性质

• 密度：
  1.331±0.06 g/cm3(Predicted)

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：
  0.2
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3'-chlorooxanilate 在 四氯化碳 、 sodium azide 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 16.33h， 生成 ethyl 1-(3-chlorophenyl)-1H-tetrazole-5-carboxylate
  参考文献：
  名称：

  Design, synthesis and biological evaluation of 1-Aryl-5-(4-arylpiperazine-1-carbonyl)-1H-tetrazols as novel microtubule destabilizers

  摘要：

  A series of 1-aryl-5-(4-arylpiperazine-1-carbonyl)-1H-tetrazols as microtubule destabilizers were designed, synthesised and evaluated for anticancer activity. Based on bioisosterism, we introduced the tetrazole moiety containing the hydrogen-bond acceptors as B-ring of XRP44X analogues. The key intermediates ethyl 1-aryl-1H-tetrazole-5-carboxylates 10 can be simply and efficiently prepared via a microwave-assisted continuous operation process. Among the compounds synthesised, compound 6-31 showed noteworthy potency against SGC-7901, A549 and HeLa cell lines. In mechanism studies, compound 6-31 inhibited tubulin polymerisation and disorganised microtubule in SGC-7901 cells by binding to tubulin. Moreover, compound 6-31 arrested SGC-7901cells in G2/M phase. This study provided a new perspective for development of antitumor agents that target tubulin.

  DOI：

  10.1080/14756366.2020.1759582
• 作为产物：
  描述：

  重氮基乙酰乙酸乙酯 、 3-氯苯胺 在 dirhodium tetraacetate 、 氧气 作用下， 以 苯 为溶剂， 反应 1.17h， 以71.6%的产率得到ethyl 3'-chlorooxanilate
  参考文献：
  名称：

  N-烷基化苯胺向N-芳基草酸酯的转化

  摘要：

  研究了将N-烷基化苯胺转化为N-芳基草酸酯的方法，研究方法是使用2-重氮乙酰乙酸乙酯作为烷基化剂，并用四乙酸二钠（Rh 2（OAc）4）作为催化剂。用许多取代的N-烷基化苯胺研究了该反应作为N-芳基草酸酯的合成方法的一般适用性。结果表明草酸盐是通过与分子O 2和Rh 2（OAc）4作为引发剂的自由基反应形成的。

  DOI：

  10.1002/hlca.201200603

文献信息

• New Highlights in the Synthesis of 4-Aryl-1,4-dihydropyrazines
  作者：Jing-Yu He、Xiu-Qing Song、Hong Yan、Ru-Gang Zhong

  DOI：10.1002/jhet.989

  日期：2012.11

  The 4‐aryl‐1,4‐dihydropyrazines were prepared via the cyclization of N,N‐bisalkylated anilines with ammonium acetate. These reactions were aided by improvements in the synthesis of N,N‐bisalkylated anilines which were alkylated with anilines using ethyl 2‐diazo acetoacetate in a reaction catalyzed by rhodium acetate in the absence of oxygen. A possible mechanistic route is postulated on the basis of

  通过将N，N-双烷基化苯胺与乙酸铵环化来制备4-芳基-1,4-二氢吡嗪。这些反应得益于N，N-双烷基化苯胺的合成的改进，N2-N-双烷基化苯胺在无氧乙酸铑的催化下，使用乙酰丙酮-2-重氮乙酯与苯胺烷基化。推测可能的机理路线是基于N烷基化中间体的分离，该中间体经1 H NMR数据和X射线衍射确定为N芳基草酸酯。
• Discovery of Cytochrome P450 4F11 Activated Inhibitors of Stearoyl Coenzyme A Desaturase
  作者：Sarah E. Winterton、Emanuela Capota、Xiaoyu Wang、Hong Chen、Prema L. Mallipeddi、Noelle S. Williams、Bruce A. Posner、Deepak Nijhawan、Joseph M. Ready

  DOI：10.1021/acs.jmedchem.8b00052

  日期：2018.6.28

  Stearoyl-CoA desaturase (SCD) catalyzes the first step in the conversion of saturated fatty acids to unsaturated fatty acids. Unsaturated fatty acids are required for membrane integrity and for cell proliferation. For these reasons, inhibitors of SCD represent potential treatments for cancer. However, systemically active SCD inhibitors result in skin toxicity, which presents an obstacle to their development

  硬脂酰辅酶A去饱和酶（SCD）催化饱和脂肪酸向不饱和脂肪酸转化的第一步。膜完整性和细胞增殖需要不饱和脂肪酸。由于这些原因，SCD抑制剂代表了潜在的癌症治疗方法。但是，具有内在活性的SCD抑制剂会导致皮肤毒性，这对它们的发展构成了障碍。我们最近描述了一系列草酸二酰胺，它们通过CYP4F11介导的代谢转化为癌症子集内的活性SCD抑制剂。在本文中，我们描述了草酸二酰胺和相关N-酰基脲的优化，以及与代谢活化和SCD抑制有关的结构-活性关系的分析。
• Synthesis and Quantitative Structure−Activity Relationships of Oxanilates as Chemical Hybridizing Agents for Wheat (<i>Triticum aestivum </i>L.)
  作者：Kajal Chakraborty、Chakravarthi Devakumar、Shiv M. S. Tomar、Rajendra Kumar

  DOI：10.1021/jf025870+

  日期：2003.2.1

  Chemical hybridizing agents (CHAs) can facilitate two-line breeding in heterosis programs of crops. Twenty-seven oxanilates having different aromatic substitutions were synthesized and screened as CHAs on two genotypes of wheat, PBW 343 and HID 2733, during two Rabi (winter) seasons, 200001 and 2001-02. The oxanilates prepared by thermal condensation of anilines with diethyl oxalate or by acylation with ethoxycarbonyl methanoyl chloride were sprayed at 1000 and 1500 ppm at the premeiotic stage of wheat, when the length of the emerging spike of the first node was 7-8 mm. Pollen sterility and spikelet sterility were measured in each treatment. Ethyl oxanilates 5, 6, and 25, containing 4-F, 4-Br, and 4-CF3 aromatic substituents, respectively, induced greater than 98% spikelet sterility, the desired level, at 1500 ppm. Quantitative structure -activity relationship analysis revealed a direct relationship between F-p and molecular mass but an inverse relationship between MR, E-S, and R in influencing the bioactivity. Several F-1 hybrids were developed using 5, and at least one showed heterosis.
• SOME DERIVATIVES OF OXANILIDE¹
  作者：CHARLES C. PRICE、BERNARD H. VELZEN

  DOI：10.1021/jo01167a005

  日期：1947.5
• Petyunin,P.A.; Zakalyuzhnyi,M.V., Journal of general chemistry of the USSR, 1964, vol. 34, p. 26 - 30
  作者：Petyunin,P.A.、Zakalyuzhnyi,M.V.

  DOI：——

  日期：——