3-(p-fluorophenyldiazo)pentane-2,4-dione | 13572-39-9

• 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-(p-fluorophenyldiazo)pentane-2,4-dione
• 英文别名: 3-(4-Fluor-phenylazo)-pentan-2,4-dion；pentane-2,3,4-trione 3-[(4-fluoro-phenyl)-hydrazone]；2,3,4-pentanetrione 3-(4-fluoro-phenyl)-hydrazone；3-[(4-Fluorophenyl)diazenyl]pentane-2,4-dione
• CAS: 13572-39-9
• 化学式: C₁₁H₁₁FN₂O₂
• 分子量: 222.219
• InChiKey: XGMCWZKSSFGNDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  58.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(p-fluorophenyldiazo)pentane-2,4-dione 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 生成 4-(4-Fluorphenylazo)-3,5-dimethylisoxazol
  参考文献：
  名称：

  Prakash,A.; Gambhir,I.R., Journal of the Indian Chemical Society, 1966, vol. 43, p. 529 - 535

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰丙酮 、 4-氟苯胺 在 盐酸 、 sodium nitrite 、 sodium acetate 作用下， 以 水 、 乙醇 为溶剂， 生成 3-(p-fluorophenyldiazo)pentane-2,4-dione
  参考文献：
  名称：

  Synthesis and antimicrobial activity of pyrazolinones and pyrazoles having benzothiazole moiety

  摘要：

  A new class of 4-arylhydrazono-1-benzothiazolyl-3-methylpyrazolin-5-ones (3a-j) and 4-arylazo-1-benzothiazolyl-3,5-dimethylpyrazoles (4a-j) were designed as pharmacophore hybrids between pyrazolinone/pyrazole and benzothiazole moiety. The target molecules were efficiently synthesized by the cyclization of various oxobutyrates/pentane-2,4-dione derivatives with 6-chloro-2-hydrazinobenzothiazole in the presence of glacial acetic acid. The compounds were evaluated for their in vitro antimicrobial activity. Preliminary study of the structure-activity relationship revealed that electron-withdrawing groups in phenyl ring had a promising effect on the antimicrobial activity. Also, correlation study has been used to establish the relationships between the antibacterial activity and physicochemical parameter clogP.

  DOI：

  10.1007/s00044-011-9642-0

文献信息

• Synthesis and antimicrobial activity of pyrazolinones and pyrazoles having benzothiazole moiety
  作者：Mohd. Amir、Sadique A. Javed、Mohd. Zaheen Hassan

  DOI：10.1007/s00044-011-9642-0

  日期：2012.7

  A new class of 4-arylhydrazono-1-benzothiazolyl-3-methylpyrazolin-5-ones (3a-j) and 4-arylazo-1-benzothiazolyl-3,5-dimethylpyrazoles (4a-j) were designed as pharmacophore hybrids between pyrazolinone/pyrazole and benzothiazole moiety. The target molecules were efficiently synthesized by the cyclization of various oxobutyrates/pentane-2,4-dione derivatives with 6-chloro-2-hydrazinobenzothiazole in the presence of glacial acetic acid. The compounds were evaluated for their in vitro antimicrobial activity. Preliminary study of the structure-activity relationship revealed that electron-withdrawing groups in phenyl ring had a promising effect on the antimicrobial activity. Also, correlation study has been used to establish the relationships between the antibacterial activity and physicochemical parameter clogP.
• 4-Fluorophenylhydrazones as potential COX-2 inhibitors: a novel, efficient, one pot solid phase synthesis, docking study and pharmacological evaluation
  作者：Vinod Kumar、Girish Kumar Gupta、Kamalneet Kaur、Randhir Singh

  DOI：10.1007/s00044-013-0566-8

  日期：2013.12

  In search of a new class of organic compounds as potential COX-2 inhibitors, various 4-Fluorophenylhydrazones (3a-3i) have been synthesized and molecular docking study was conducted. All the synthesized compounds were also evaluated for their in vivo anti-inflammatory potential using carrageenan-induced rat paw odema method. In the present manuscript, a novel, simple, and greener protocol has been developed for the first time to prepare the hydrazo compounds by a one pot solid phase reaction between various active methylene compounds and p-fluoroaniline in the presence of p-toluene sulfonic acid as a new solid phase organocatalyst. The catalyst dramatically facilitates the reaction under solvent-free condition at moderate temperature (10-15 A degrees C). The present protocol not only provides an expeditious route to prepare hydrazo compounds in excellent yields (with in 3-5 min) but also avoids the use of two step conventional methods, and formation of side products. The results obtained from in vivo anti-inflammatory activity through carrageenan-induced rat paw odema assay showed that compounds 3a-3b, and 3d displayed excellent level of activity which was further supported by molecular docking study. A cyclooxygenase-II inhibitory molecular docking study has been carried out using (pdb: 1CX2) via Molegro Virtual Docker version 4.2.1. All the compounds were found to exhibit good level of inhibition and binding in the enzyme active site. Compounds 3a-3b, 3d, and 3e have been found to display high moldock scores -118.333, -118.778, -118.422, and -111.13, respectively, and are strongly bound with Arg120, Tyr355, His90, and Arg513 amino acids, which are responsible for COX-2 inhibition within the active site. In the present investigation, it can be concluded that the best scored inhibitors with good in vivo anti-inflammtory activity will have better chances to be used as anti-inflammatory leads.
• Prakash,A.; Gambhir,I.R., Journal of the Indian Chemical Society, 1966, vol. 43, p. 529 - 535
  作者：Prakash,A.、Gambhir,I.R.

  DOI：——

  日期：——