6-(2-氯苯甲酰基)-3H-1,3-苯并恶唑-2-酮 | 72766-68-8

• 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: 6-(2-氯苯甲酰基)-3H-1,3-苯并恶唑-2-酮
• 英文名称: 6-(2-chlorobenzoyl)-2-benzoxazolinone
• 英文别名: 6-(2-chlorobenzoyl)-2(3H)-benzoxazolone；2-BENZOXAZOLINONE, 6-(o-CHLOROBENZOYL)-；6-(2-chlorobenzoyl)-3H-1,3-benzoxazol-2-one
• CAS: 72766-68-8
• 化学式: C₁₄H₈ClNO₃
• mdl: MFCD01664249
• 分子量: 273.675
• InChiKey: ZBBOBISKWSAIAQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.424±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  6-(2-氯苯甲酰基)-3H-1,3-苯并恶唑-2-酮 在 盐酸 、 乙醇 、 sodium 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.25h， 生成 6-(o-Chlorobenzoyl)-alpha-methyl-2-oxo-3-benzoxazolineacetic acid
  参考文献：
  名称：

  Renard; Lesieur; Lespagnol, European Journal of Medicinal Chemistry, 1980, vol. 15, # 5, p. 453 - 456

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(2-氯苯甲酰基)-1,3-苯并恶唑-2-酮 在 PPA 作用下， 反应 1.5h， 以80%的产率得到6-(2-氯苯甲酰基)-3H-1,3-苯并恶唑-2-酮
  参考文献：
  名称：

  Cotelle, Nicole; Cotelle, Philippe; Lesieur, Daniel, Synthetic Communications, 1989, vol. 19, # 18, p. 3259 - 3266

  摘要：

  DOI：

文献信息

• Analgesic and Antiinflammatory Effects of Some New 6-Acyl-3-substituted-2(3H)-benzoxazolone Derivatives
  作者：Dilek Demir Erol、Rumeysa Demirdamar (Sunal)、Suna Duru

  DOI：10.1002/jps.2600830302

  日期：1994.3

  6-Acyl-2(3H)-benzoxazolone derivatives were reacted with 4-substituted phenacyl bromide in ethanol to give the corresponding 6-acyl-3-[(4-substitutedbenzoyl)methyl]-2(3H)-benzoxazolones . The compounds were screened for their analgesic, antiinflammatory activities. The eight compounds synthesized showed high analgesic activities and further investigation revealed compounds 3, 6 and 7 to be potent inhibitors

  使6-酰基-2（3H）-苯并恶唑酮衍生物与4-取代的苯甲酰溴在乙醇中反应，得到相应的6-酰基-3-[（4-取代的苯甲酰基）甲基] -2（3H）-苯并恶唑啉酮。筛选化合物的镇痛，抗炎活性。合成的八种化合物显示出很高的镇痛活性，进一步的研究表明，化合物3、6和7是角叉菜胶和花生四烯酸诱导的爪水肿的有效抑制剂。从角叉菜胶爪水肿液中分离出的PGE2在用化合物3、6和7治疗的小鼠中也显着降低。
• Analgesic Activity of Some 3-(Arylpiperidinomethyl)-2-benzoxazolinone Derivatives
  作者：Hakki Erdo??an、Serdar Ünlü、Rümeysa Sunal

  DOI：10.1002/ardp.19893220204

  日期：——

  In our previous study1,2), the antimicrobial activities of 16 new compounds synthetized by reacting 2‐benzoxazolinones with derivatives of piperidine were determined. In this study, the analgesic activities of these compounds, using modified Koster's test is investigated. The analgesic activities of these compounds are higher than that of O‐acetyl salicilic acid.

  在我们之前的研究 1,2) 中，确定了 16 种通过 2-苯并恶唑啉酮与哌啶衍生物反应合成的新化合物的抗菌活性。在这项研究中，使用改进的 Koster 检验研究了这些化合物的镇痛活性。这些化合物的镇痛活性高于O-乙酰水杨酸。
• Synthesis and Analgesic and Anti-inflammatory Activity of Some New (6-Acyl-2-benzoxazolinone and 6-Acyl-2-benzothiazolinone Derivatives with Acetic Acid and Propanoic Acid Residues
  作者：Serdar Ünlü、Tijen Önkol、Yasemin Dündar、Berna Ökçelik、Esra Küpeli、Erdem Yeşilada、Ningur Noyanalpan、M. Fethi Şahin

  DOI：10.1002/ardp.200300746

  日期：2003.8

  In this study for developing potent analgesic and anti‐inflammatory compounds, we synthesized 6‐acyl‐2‐benzoxazolinone and 6‐acyl‐2‐benzothiazolinone derivatives with acetic acid and propanoic acid side chain, and performed preliminary screening of their in vivo analgesic and anti‐inflammatory activities at a single dose of 100 mg/kg inmice by a p‐benzoquinone‐induced writhing test and a Carrageenaninduced

  在开发强效镇痛抗炎化合物的研究中，我们合成了具有乙酸和丙酸侧链的 6-酰基-2-苯并恶唑啉酮和 6-酰基-2-苯并噻唑啉酮衍生物，并初步筛选了它们的体内镇痛和抗炎作用。分别通过 β-苯醌诱导的扭体试验和角叉菜胶诱导的后爪水肿模型对小鼠单剂量 100 mg/kg 的抗炎活性进行测定。我们还确定了它们对受试动物的胃溃疡作用。普遍发现丙酸衍生物具有较高的镇痛和抗炎活性，其中，3-（6-苯甲酰基-2-苯并噻唑啉酮-3-基）丙酸（化合物4a）表现出最高的镇痛和抗炎活性活动。然而，所有化合物的抗炎作用均低于我们在 10 mg/kg 剂量下观察到的吲哚美辛。因此，具有丙酸侧链的 6-酰基-2-苯并恶唑啉酮/2-苯并噻唑啉酮可能会导致进一步研究以开发具有强效镇痛和抗炎作用的更好候选物，而乙酸衍生物则没有表现出可比的令人满意的特性。
• Synthesis and antibacterial and antifungal properties of thiazolinoethyl-2(3H)-benzoxazolone derivatives. II
  作者：DD Erol、MD Aytemir、N Yuluĝ

  DOI：10.1016/0223-5234(96)85883-1

  日期：1996.1

  Cyano derivatives of 6-acyl-2(3H)-benzoxazolones were reacted with cysteamine HCl in ethanol to give the corresponding 6-acyl-3-thiazolinoethyl-2(3H)-benzoxazolones and their antibacterial and antifungal activities were investigated. The chemical structures were proved by means of their IR and H-1-NMR spectra and elemental analysis. Investigation of antimicrobial activity of the compounds was carried out by tube dilution and disc techniques using bacteria (Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923, Pseudomonas aeruginosa ATCC 27853 and Streptococcus faecalis ATCC 29212) and yeast-like fungi (Candida parapsilosis, C albicans, C pseudotropicalis and C stellatoidea). Inhibitory effects were observed for many compounds against S aureus and Bacillus subtilis. Compounds 13 and 15 had minimum inhibitory concentrations (MIG) of 8.4 and 4.2 mu g/mL respectively. The antifungal studies against C albicans (10 and 16, MIC = 67.5 mu g/mL), C parapsilosis (15, MIC = 67.5 mu g/mL) and C stellaatoidea (9, MIC = 67.5 mu g/mL) were more successful in comparison.
• Synthesis of 3-(2-pyridylethyl)benzoxazolinone derivatives: potent analgesic and antiinflammatory compounds inhibiting prostaglandin E2
  作者：Cihat Safak、Hakki Erdogan、Erhan Palaska、Rumeysa Sunal、Suna Duru

  DOI：10.1021/jm00085a018

  日期：1992.4

  Fourteen new 3-[2-(2- and/or 4-pyridyl)ethyl]benzoxazolinone derivatives have been synthesized by reacting 2- and/or 4-vinylpyridine and appropriate benzoxazolinones. Their chemical structures have been proven by IR, H-1-NMR, and elemental analysis. Analgesic activities of these compounds were investigated by a "Modified Koster's Test". Except for compounds 10 and 11, all the new derivatives showed higher analgesic activities than aspirin. Therefore the compounds were screened for their antiinflammatory activities using the carrageenan hind paw edema test. The compounds (6, 7, 8, 9, 14, and 17) that showed high antiinflammatory activity were then further screened for their ability to inhibit prostaglandin E2 (PGE2) induced paw edema. Although all the benzoxazolinone derivatives synthesized in this study showed higher antiinflammatory activity compared to indomethacin, those without a substituent at the 6-position of the ring were significantly more active than the rest of the group, and their ulcerogenic activities and ED50 values indicate them as promising derivatives for further study.