4-dichloromethylene-p-tolyl-1,3-oxazol-5(4H)-one | 61767-34-8

• 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: 4-dichloromethylene-p-tolyl-1,3-oxazol-5(4H)-one
• 英文别名: 2-(4-methylphenyl)-4-dichloromethylideneoxazol-5(4H)-one；4-dichloromethylene-2-p-tolyl-4H-oxazol-5-one；5(4H)-Oxazolone, 4-(dichloromethylene)-2-(4-methylphenyl)-；4-(dichloromethylidene)-2-(4-methylphenyl)-1,3-oxazol-5-one
• CAS: 61767-34-8
• 化学式: C₁₁H₇Cl₂NO₂
• 分子量: 256.088
• InChiKey: OJMRYZVUUKELRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-dichloromethylene-p-tolyl-1,3-oxazol-5(4H)-one 在 劳森试剂 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 为溶剂， 反应 75.0h， 生成 2-(5-methylthio-2-p-tolyl-1,3-oxazol-4-yl)-1,3-benzothiazole
  参考文献：
  名称：

  10.1023/b:rugc.0000031875.13196.08

  摘要：

  DOI：

  10.1023/b:rugc.0000031875.13196.08
• 作为产物：
  描述：

  3,3-dichloro-2-(4-methyl-benzoylamino)-acrylic acid 在 五氯化磷 作用下， 以 苯 为溶剂， 反应 0.25h， 生成 4-dichloromethylene-p-tolyl-1,3-oxazol-5(4H)-one
  参考文献：
  名称：

  Drach,B.S. et al., Russian Journal of Organic Chemistry, 1976, vol. 12, p. 2170 - 2175

  摘要：

  DOI：

文献信息

• Design, synthesis and evaluation of the anti-breast cancer activity of 1,3-oxazolo[4,5-<i>d</i>]pyrimidine and 1,3-oxazolo[5,4-<i>d</i>]pyrimidine derivatives
  作者：Yevheniia Velihina、Raey Gesese、Victor Zhirnov、Oleksandr Kobzar、Benjamin Bui、Stepan Pilyo、Andriy Vovk、Hai-Ying Shen、Volodymyr Brovarets

  DOI：10.1039/d2md00377e

  日期：——

  A series of 1,3-oxazolo[4,5-d]pyrimidine and 1,3-oxazolo[5,4-d]pyrimidine derivatives were synthesized and functionalized in this study. The obtained compounds were tested against breast cancer cell lines of the NCI subpanel, followed by further analysis using the COMPARE algorithm from the Therapeutics Development Program, NCI. All synthesized derivatives displayed activity against most cell lines

  本研究合成并功能化了一系列1,3-恶唑并[4,5- d ]嘧啶和1,3-恶唑并[5,4- d ]嘧啶衍生物。获得的化合物针对 NCI 子组的乳腺癌细胞系进行了测试，然后使用 NCI 治疗开发计划的 COMPARE 算法进行进一步分析。就所有研究参数而言，所有合成的衍生物在微摩尔浓度范围内均表现出针对大多数细胞系的活性。恶唑并嘧啶5表现出最高的抗肿瘤活性。化合物的标准COMPARE分析表明，衍生物10和11的细胞毒活性载体与他莫昔芬表现出接近非常高的相关性，恶唑并嘧啶13与相同药物表现出非常高的相关性。五种衍生物（ 2、4、6、11和13 ）与 TGI 载体中的阿克拉霉素A 表现出高度相关性。同时，化合物1在培养的MDA-MB 231细胞系中有效抑制ADK，表明ADK是其发挥抗癌特性的靶标之一。根据分子对接结果，提出了恶唑并嘧啶1与ADK可能的结合模式。
• Conversion of 2-aryl-4-dichloromethylen-5(4H)oxazolones to 5-acylamino-substituted pyrimidine bases
  作者：V. M. Prokopenko、V. N. Sviripa、S. G. Pil’o、V. S. Brovarets、A. N. Chernega、B. S. Drach

  DOI：10.1134/s1070363209030256

  日期：2009.3

  Available polycentral unsaturated azlactones with 4-dichloromethylene group by successive treating with benzamidine and then with morpholine or its analogs were converted to substituted 5-acylamino-4-hydroxypyrimidines containing the residues of the corresponding nitrogen bases in the position 6. The structure of these cyclization products is consistent with the scheme of their preparation and has been confirmed also by H-1 NMR spectroscopy and XRD analysis.
• Successive reaction of 2-aryl-4-dichloromethylideneoxazol-54H-ones with 2-amino-1,3-thiazoles and strongly basic nitrogen-containing reagents
  作者：V. M. Prokopenko、V. N. Sviripa、V. S. Brovarets、E. B. Rusanov、B. S. Drach

  DOI：10.1134/s1070363208040221

  日期：2008.4

  Treatment of 2-aryl-4-dichloromethylideneoxazole-5(4H)-ones first with 2-aminothiazoles and then with benzylamine, piperidine, or morpholine gave the corresponding 5-amino-4-(1,3-thiazol-2-ylcarbamoyl)-1,3-oxazole derivatives whose structure was confirmed by a combination of spectral data and X-ray analysis.
• DRACH B. S.; MARTYNYUK A. P.; MISKEVICH G. N., ZH. ORGAN. XIMII, 1976, 12, HO 10, 2238-2244
  作者：DRACH B. S.、 MARTYNYUK A. P.、 MISKEVICH G. N.

  DOI：——

  日期：——
• Reaction of 2-aryl-4-dichloromethylidene-1,3-oxazol-5(4H)-ones with 2-aminopyridine
  作者：V. M. Prokopenko、S. G. Pil’o、V. S. Brovarets、A. N. Vasilenko、B. S. Drach

  DOI：10.1134/s1070363210010160

  日期：2010.1

  Reactions of multicenter electrophilic substrates, 2-aryl-4-dichloromethylidene-1,3-oxazol-5(4H)-ones, with 2-aminopyridine, involved cleavage of the dihydrooxazole ring by the primary amino group of nucleophilic reagent and subsequent cyclization to imidazopyridine derivatives. The latter reacted with morpholine and its analogs via recyclization with formation of 5-amino-2-aryl-N-(pyridin-2-yl)-1,3-oxazole-4-carboxamides.