6-benzoyl-5-chloro-2-benzoxazolinone | 95637-39-1

• 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: 6-benzoyl-5-chloro-2-benzoxazolinone
• 英文别名: 2(3H)-Benzoxazolone, 6-benzoyl-5-chloro-；6-benzoyl-5-chloro-3H-1,3-benzoxazol-2-one
• CAS: 95637-39-1
• 化学式: C₁₄H₈ClNO₃
• 分子量: 273.675
• InChiKey: BXNDIHHIQQSMEY-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-benzoyl-5-chloro-2-benzoxazolinone 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 6-Benzoyl-5-chloro-3-[2-(4,5-dihydro-1,3-thiazol-2-yl)ethyl]-1,3-benzoxazol-2-one
  参考文献：
  名称：

  Synthesis and antibacterial and antifungal properties of thiazolinoethyl-2(3H)-benzoxazolone derivatives. II

  摘要：

  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.

  DOI：

  10.1016/0223-5234(96)85883-1
• 作为产物：
  描述：

  氯唑沙宗 、 苯甲酸 在 PPA 作用下， 生成 6-benzoyl-5-chloro-2-benzoxazolinone
  参考文献：
  名称：

  Palaska; Unlu; Ozkanli, Arzneimittel-Forschung/Drug Research, 1995, vol. 45, # 6, p. 693 - 696

  摘要：

  DOI：

文献信息

• 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。
• Palaska, Erhan; Goekhan, Nesrin; Erdogan, Hakki, Arzneimittel-Forschung/Drug Research, 1999, vol. 49, # 9, p. 754 - 758
  作者：Palaska, Erhan、Goekhan, Nesrin、Erdogan, Hakki、Tel, Banu Cahide、Demirdamar, Ruemeysa

  DOI：——

  日期：——
• ERDOGAN, HAKKI;UNLU, SERDAR;SUNAL, RUMEYSA, ARCH. PHARM., 322,(1989) N, C. 75-77
  作者：ERDOGAN, HAKKI、UNLU, SERDAR、SUNAL, RUMEYSA

  DOI：——

  日期：——
• [EN] NOVEL SUBSTITUTED 3H -BENZOXAZOLE-2-THIONES AND 3H -BENZOTHIAZOLE-2 THIONES DERIVATIVES, METHOD FOR PREPARING THEM AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] NOUVEAUX DERIVES [3H]-BENZOXAZOLE-2-THIONES ET [3H]-BENZOTHIAZOLE-2-THIONES SUBSTITUES, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT
  申请人：ADIR ET COMPAGNIE

  公开号：WO1998025913A1

  公开（公告）日：1998-06-18

  (EN) The invention concerns compounds of general formula (I) in which: R1 represents a hydrogen atom or a C1-C6 alkyl group, linear or branched; R2 represents a hydrogen atom, a C1-C6 alkyl group linear or branched, a halogen atom, a C1-C6 alkoxy group, linear or branched or C1-C6 trihalogenoalkyl group, linear or branched; X represents a hydrogen atom; Y represents a hydrogen atom or a hydroxyl group, or X and Y together form an oxo group; Z represents an oxygen atom or a sulphur atom; Ar represents an aromatic group selected among phenyl, naphthyl, substituted phenyl, substituted naphthyl or a heterocyclic group selected among pyridyl, pyrazinyl, pyrimidinyl, indolyl, quinolyl, pyrrolyl, thienyl, benzothienyl, furyl, each of these heterocyclic groups being optionally substituted, their geometrical and/or optical isomers, and their additive salts to a pharmaceutically acceptable acid or base. The compounds have particularly interesting peripheral analgesic therapeutic properties.(FR) L'invention concerne les composés de formule générale (I) dans laquelle: R1 représente un atome d'hydrogène ou un groupement alkyle (C1-C6) linéaire ou ramifié; R2 représente un atome d'hydrogène, un groupement alkyle (C1-C6) linéaire ou ramifié, un atome d'halogène, un groupement alkoxy (C1-C6) linéaire ou ramifié ou trihalogénoalkyle (C1-C6) linéaire ou ramifié; X représente un atome d'hydrogène; Y représente un atome d'hydrogène ou un groupement hydroxy, ou X et Y forment ensemble un groupement oxo; Z représente un atome d'oxygène ou un atome de soufre; Ar représente un groupement aromatique choisi parmi phényle, naphtyle, phényle substitué, naphtyle substitué ou un groupement hétéroaromatique choisi parmi pyridyle, pyrazinyle, pyrimidinyle, indolyle, quinolyle, pyrrolyle, thiényle, benzothiényle, furyle, chacun de ces groupements hétéroaromatiques étant éventuellement substitué, leurs isomères géométriques et/ou optiques, et leurs sels d'addition à un acide ou une base, pharmaceutiquement acceptables. Les composés de la présente invention montrent des propriétés thérapeutiques analgésiques périphériques particulièrement intéressantes.