5-(4-氯苯基)异噁唑-3-羰肼 | 91587-71-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-(4-氯苯基)异噁唑-3-羰肼
• 英文名称: 5-(4-Chlorphenyl)-isoxazolcarbonsaeure-(3)-hydrazid
• 英文别名: 5-(4-chlorophenyl)isoxazole-3-carbohydrazide；5-(4-chloro-phenyl)-isoxazole-3-carboxylic acid hydrazide；5-(4-chlorophenyl)-1,2-oxazole-3-carbohydrazide
• CAS: 91587-71-2
• 化学式: C₁₀H₈ClN₃O₂
• mdl: MFCD08446411
• 分子量: 237.645
• InChiKey: LAFWUHGEVDKVFY-UHFFFAOYSA-N

物化性质

• 熔点：
  217-218 °C(Solv: ethanol (64-17-5))
• 密度：
  1.396±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.2
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  5-(4-氯苯基)异噁唑-3-羰肼 在 sodium acetate 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 7.0h， 生成 5-(4-chlorophenyl)-N'-[5-(4-fluorobenzylidene)-4-oxo-3-phenylthiazolidin-2-ylidene]-isoxazole-3-carbohydrazide
  参考文献：
  名称：

  Synthesis, anti-HSV-1, and cytotoxic activities of some new pyrazole- and isoxazole-based heterocycles

  摘要：

  Ethyl 2,4-dioxo-4-(p-chloro)phenylbutyrate 2 obtained by condensation of 4-chloroacetophenone with diethyl oxalate was converted to 5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carbohydrazide 5 and 5-(4-chlorophenyl)isoxazole-3-carbohydrazide 6 in good yields. Treatment of 5 or 6 with phenylisothiocyanate and reaction of the resulting thiosemicarbazide 7 or 8 with chloroacetic acid and 4-fluorobenzaldehyde, phenacyl bromides gave the corresponding 4-thiazolidinone 9 or 10 or 1,3-thiazoles 11 or 12, respectively. While the intramolecular cyclization of 7 or 8 in concentrated sulfuric acid afforded 1,3,4-thiadiazoles 13 or 14. The reactivity of hydrazide 5 or 6 towards fluorinated aldehyde, hydrazonoyl chloride, and beta-ketoester was studied to give fluorinated hydrazones, bis-hydrazones, and pyrazoles 15-23. The newly synthesized compounds were screened for their antiviral activity, and compound 19 reduced the number of viral plaques of Herpes simplex type-1 (HSV-1) by 69%. The detailed synthesis and spectroscopic and biological data are reported.

  DOI：

  10.1007/s00044-010-9420-4
• 作为产物：
  描述：

  4-(4-氯苯基)-2,4-二氧代丁酸乙酯 在 盐酸羟胺 、 sodium carbonate 、 一水合肼 作用下， 以 乙醇 、 水 、 异丙醇 为溶剂， 反应 2.0h， 生成 5-(4-氯苯基)异噁唑-3-羰肼
  参考文献：
  名称：

  Synthesis of 5-Substituted 3-Isoxazolecarboxylic Acid Hydrazides and Derivatives

  摘要：

  DOI：

  10.1021/jo01064a050

文献信息

• Synthesis of New Symmetrical <i>N, N</i>'-Diacylhydrazines and 2-(1,2,3- Triazol-4-yl)-1,3,4-oxadiazoles
  作者：Bakr F. Abdel-Wahab、Mohammad Hayal Alotaibi、Gamal A. El-Hiti

  DOI：10.2174/1570178614666170524130223

  日期：2017.8.22

  Background: The aim of the current research was to synthesize novel symmetrical N,N'- diacylhydrazines through oxidation of acid carbohydrazide using ethyl 2-cyano-3-methoxyacrylate or 2-(methoxymethylene)malononitrile as organo-catalyst. Also, novel 2-(1,2,3-triazol-4-yl)-1,3,4- oxadiazoles from the reaction of acid carbohydrazides with various carboxylic acids in boiling phosphoryl chloride were

  背景：当前研究的目的是通过使用2-氰基-3-甲氧基丙烯酸乙酯或2-（甲氧基亚甲基）丙二腈作为有机催化剂氧化酸性碳酰肼来合成新型对称的N，N'-二酰基肼。另外，在沸腾的磷酰氯中，由酸性碳酰肼与各种羧酸反应，合成了新型的2-（1,2,3-三唑-4-基）-1,3,4-恶二唑。 方法：采用简便的合成方法，使用市售化学品合成目标化合物。同样，通过使用分析和光谱数据以及单一的X射线晶体结构来阐明获得的产物的结构。 结果：方便地合成了一系列新颖的对称N，N'-二酰基肼，2-（1,2,3-三唑-4-基）-1,3,4-恶二唑和醛N-酰基hydr。和简单的程序。 结论：引入了新的一步合成方法，可生产多种对称的N，N'-二酰基肼和2-（1,2,3-三唑-4-基）-1,3,4-恶二唑，得自相应的酰肼。
• Exploring rhodanine linked enamine–carbohydrazide derivatives as mycobacterial carbonic anhydrase inhibitors: Design, synthesis, biological evaluation, and molecular docking studies
  作者：Sarvan Maddipatla、Bulti Bakchi、Rutuja Rama Gadhave、Andrea Ammara、Shashikanta Sau、Bandela Rani、Srinivas Nanduri、Nitin Pal Kalia、Claudiu T. Supuran、Venkata Madhavi Yaddanapudi

  DOI：10.1002/ardp.202400064

  日期：——

  exploring their potential as inhibitors of mycobacterial carbonic anhydrase. The findings reveal their efficacy, displaying notable selectivity toward the mycobacterial carbonic anhydrase 2 (mtCA 2) enzyme. While exhibiting moderate activity against human carbonic anhydrase isoforms, this series demonstrates promising selectivity, positioning these compounds as potential antitubercular agents. Compound 6d

  随着耐多药结核病的兴起，寻找一种结合新作用机制的替代性优质治疗方案变得至关重要。为了实现这一目标，我们开发并合成了一系列新的绕丹宁连接的烯胺碳酰肼衍生物，探索它们作为分枝杆菌碳酸酐酶抑制剂的潜力。研究结果揭示了它们的功效，对分枝杆菌碳酸酐酶 2 (mtCA 2) 酶表现出显着的选择性。该系列化合物虽然对人碳酸酐酶异构体表现出中等活性，但表现出良好的选择性，将这些化合物定位为潜在的抗结核药物。化合物6d是该系列中最好的一种，对 mtCA 2 的K i值为 9.5 µM。大多数化合物对 Mtb H37Rv 菌株表现出中等至良好的抑制作用；化合物11k的最低抑制浓度为 1 µg/mL。分子对接研究表明，化合物6d和11k显示出与锌离子的金属配位，就像经典的 CA 抑制剂一样。
• Synthesis of 5-Substituted 3-Isoxazolecarboxylic Acid Hydrazides and Derivatives
  作者：THOMAS S. GARDNER、E. WENIS、JOHN LEE

  DOI：10.1021/jo01064a050

  日期：1961.5
• Synthesis of New Glucose-containing 5-Arylisoxazoles and their Enzyme Inhibitory Activity
  作者：Roshanak Hariri、Aida Iraji、Somayeh Mojtabavi、Mina Saeedi、Mohammad Ali Faramarzi、Mohsen Amini、Tahmineh Akbarzadeh

  DOI：10.2174/0115701786283334231228104931

  日期：2024.6

  Carbohydrates are an important group of biomolecules that have received special attention due to their significant role in the design and synthesis of new bioactive compounds. In this study, a new class of 5-arylisoxazole-glucose hybrids was designed and synthesized for evaluation of their inhibitory effects on α-glucosidase, α-amylase, and tyrosinase. The target compounds depicted selective α-glucosidase inhibitory activity over α-amylase, which is an important factor in reducing probable gastrointestinal problems in the treatment of type 2 diabetes. In this respect, compound 9a, possessing the phenylisoxazole group, was found to be the most potent α-glucosidase inhibitor (IC50 = 292.2 ± 0.1 μM) compared to acarbose (IC50 = 750.2 ± 0.1 μM) as the positive control. All compounds were also evaluated for their anti-tyrosinase effect, and among them, compound 9j, containing a fluoroaryl moiety, showed potent activity (IC50 = 50.1 ± 6.3 μM) in comparison to kojic acid (IC50 = 23.6 ± 2.6 μM). Also, docking studies were performed to investigate the probable mode of action, which indicated the construction of important H-bonding interactions between the sugar moiety and the enzyme’s active sites. According to the results, hybrids containing heterocycles attached to glucose can be used to inhibit α-glucosidase.
• Synthesis, anti-HSV-1, and cytotoxic activities of some new pyrazole- and isoxazole-based heterocycles
  作者：Kamal M. Dawood、Hassan Abdel-Gawad、Hanan A. Mohamed、Farid A. Badria

  DOI：10.1007/s00044-010-9420-4

  日期：2011.9

  Ethyl 2,4-dioxo-4-(p-chloro)phenylbutyrate 2 obtained by condensation of 4-chloroacetophenone with diethyl oxalate was converted to 5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carbohydrazide 5 and 5-(4-chlorophenyl)isoxazole-3-carbohydrazide 6 in good yields. Treatment of 5 or 6 with phenylisothiocyanate and reaction of the resulting thiosemicarbazide 7 or 8 with chloroacetic acid and 4-fluorobenzaldehyde, phenacyl bromides gave the corresponding 4-thiazolidinone 9 or 10 or 1,3-thiazoles 11 or 12, respectively. While the intramolecular cyclization of 7 or 8 in concentrated sulfuric acid afforded 1,3,4-thiadiazoles 13 or 14. The reactivity of hydrazide 5 or 6 towards fluorinated aldehyde, hydrazonoyl chloride, and beta-ketoester was studied to give fluorinated hydrazones, bis-hydrazones, and pyrazoles 15-23. The newly synthesized compounds were screened for their antiviral activity, and compound 19 reduced the number of viral plaques of Herpes simplex type-1 (HSV-1) by 69%. The detailed synthesis and spectroscopic and biological data are reported.