3-[3-(4-Chlorophenyl)-1,2-oxazol-5-yl]propanoic acid | 1422283-23-5

• 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: 3-[3-(4-Chlorophenyl)-1,2-oxazol-5-yl]propanoic acid
• 英文别名: 3-[3-(4-chlorophenyl)-1,2-oxazol-5-yl]propanoic acid
• CAS: 1422283-23-5
• 化学式: C₁₂H₁₀ClNO₃
• 分子量: 251.669
• InChiKey: IPWYDJUPQCFKIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[3-(4-Chlorophenyl)-1,2-oxazol-5-yl]propanoic acid 在 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以94%的产率得到3-(4-chlorophenyl)-4-fluoro-1,6-dioxa-2-azaspiro[4.4]non-2-en-7-one
  参考文献：
  名称：

  氟取代螺异恶唑啉作为潜在抗病毒和抗癌药物的合成和生物学评价

  摘要：

  亲电氟介导的脱芳香螺环化已被开发用于合成一系列氟取代的螺异恶唑啉醚和内酯。对合成化合物进行体外生物学测定，探讨其对人巨细胞病毒 (HCMV) 的抗病毒活性以及对胶质母细胞瘤 (GBM6) 和三阴性乳腺癌 (MDA MB 231) 的细胞毒性。有趣的是，化合物4d和4n显示出显着的抗HCMV活性（IC 50 ∼ 10 μM），而4l和5f显示出最高的细胞毒性，IC 50 = 36 〜 80 μM。合成功效和生物学相关性为进一步开发氟螺螺异恶唑啉作为新型抗病毒和抗癌药物提供了机会。

  DOI：

  10.1039/d0ra06148d
• 作为产物：
  描述：

  4-chlorobenzaldoxime 在 N-氯代丁二酰亚胺 、 copper diacetate 、 potassium hydrogencarbonate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 1.0h， 生成 3-[3-(4-Chlorophenyl)-1,2-oxazol-5-yl]propanoic acid
  参考文献：
  名称：

  Larvicidal isoxazoles: Synthesis and their effective susceptibility towards Aedes aegypti larvae

  摘要：

  Twenty 3,5-disubstituted isoxazoles have been synthesized and tested against fourth instar Aedes aegypti larvae. In the synthesis of title compounds, modifications have been made in the C-5 side-chain with a view to test their larvicidal activity. These isoxazoles have been obtained by 1,3-dipolar cycloaddition of arylnitrile oxides to terminal alkynes which furnished the desired products in 20% to 79% yields. A comparative study of the larvicidal activity between 3-(3-aryl-isoxazol-5-yl)-propan-1-ols and 3-(3-aryl-isoxazol-5-yl)-propionic acids clearly demonstrated that the latter compounds possess much better larvicidal activity than the former. We also tested two esters, viz., methyl 3-[3-(phenyl)-isoxazole-5-yl] propionate and methyl 3-[3-(4-chlorophenyl)-isoxazole-5-yl] propionate, where the latter presented an excellent larvicidal profile. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.006

文献信息

• Bromo-lactamization of isoxazole <i>via</i> neighboring group participation: toward spiro-isoxazoline γ- and δ-lactams
  作者：Prasanta Das、Cord Carter、Gulrukh Shaheen、Ashton T. Hamme

  DOI：10.1039/d2ra01070d

  日期：——

  natural products and synthetic units to investigate their novel biological activities. Herein, a bromo-lactamization mediated neighboring group participation approach has been utilized on various isoxazole-amides to construct an array of spiro-isoxazoline-lactams. The easy synthesis with diverse functionalization in the periphery of a novel 3D framework could be interesting for biomedical investigation

  含有天然产物和合成类似物的螺杂环由于其刚性的 3D 构象和结构含义而具有更广泛的生物医学应用。在这种背景下，构建螺异恶唑啉系统继续引起我们对天然产物和合成单元的兴趣，以研究其新颖的生物活性。在此，溴内酰胺化介导的邻近基团参与方法已用于各种异恶唑酰胺，以构建一系列螺异恶唑啉内酰胺。在新颖的 3D 框架外围进行具有多种功能化的简单合成对于生物医学研究可能会很有趣。
• Larvicidal isoxazoles: Synthesis and their effective susceptibility towards Aedes aegypti larvae
  作者：Diana C.B. da Silva-Alves、Janaína V. dos Anjos、Nery N.M. Cavalcante、Geanne K.N. Santos、Daniela M.do A.F. Navarro、Rajendra M. Srivastava

  DOI：10.1016/j.bmc.2012.12.006

  日期：2013.2

  Twenty 3,5-disubstituted isoxazoles have been synthesized and tested against fourth instar Aedes aegypti larvae. In the synthesis of title compounds, modifications have been made in the C-5 side-chain with a view to test their larvicidal activity. These isoxazoles have been obtained by 1,3-dipolar cycloaddition of arylnitrile oxides to terminal alkynes which furnished the desired products in 20% to 79% yields. A comparative study of the larvicidal activity between 3-(3-aryl-isoxazol-5-yl)-propan-1-ols and 3-(3-aryl-isoxazol-5-yl)-propionic acids clearly demonstrated that the latter compounds possess much better larvicidal activity than the former. We also tested two esters, viz., methyl 3-[3-(phenyl)-isoxazole-5-yl] propionate and methyl 3-[3-(4-chlorophenyl)-isoxazole-5-yl] propionate, where the latter presented an excellent larvicidal profile. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of fluoro-substituted spiro-isoxazolines as potential anti-viral and anti-cancer agents
  作者：Prasanta Das、Sarah Boone、Dipanwita Mitra、Lindsay Turner、Ritesh Tandon、Drazen Raucher、Ashton T. Hamme

  DOI：10.1039/d0ra06148d

  日期：——

  Electrophilic fluorine-mediated dearomative spirocyclization has been developed to synthesize a range of fluoro-substituted spiro-isoxazoline ethers and lactones. The in vitro biological assays of synthesized compounds were probed for anti-viral activity against human cytomegalovirus (HCMV) and cytotoxicity against glioblastomas (GBM6) and triple negative breast cancer (MDA MB 231). Interestingly,

  亲电氟介导的脱芳香螺环化已被开发用于合成一系列氟取代的螺异恶唑啉醚和内酯。对合成化合物进行体外生物学测定，探讨其对人巨细胞病毒 (HCMV) 的抗病毒活性以及对胶质母细胞瘤 (GBM6) 和三阴性乳腺癌 (MDA MB 231) 的细胞毒性。有趣的是，化合物4d和4n显示出显着的抗HCMV活性（IC 50 ∼ 10 μM），而4l和5f显示出最高的细胞毒性，IC 50 = 36 〜 80 μM。合成功效和生物学相关性为进一步开发氟螺螺异恶唑啉作为新型抗病毒和抗癌药物提供了机会。