1-benzyl-5-phenyl-4-imidazolin-2-one | 83229-99-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-benzyl-5-phenyl-4-imidazolin-2-one
• 英文别名: 3-benzyl-4-phenyl-1H-imidazol-2-one
• CAS: 83229-99-6
• 化学式: C₁₆H₁₄N₂O
• 分子量: 250.3
• InChiKey: HMDSNARTJMKEKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8-溴辛酸甲酯 、 1-benzyl-5-phenyl-4-imidazolin-2-one 在 NaH 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 生成 8-(3-benzyl-2-oxo-4-phenyl-4-imidazolin-1-yl) caprylic acid methyl ester
  参考文献：
  名称：

  N-Substituted .omega.-(2-oxo-4-imidazolin-1-yl) alcanoic acids and salts

  摘要：

  本发明涉及N-取代的ω-(2-氧代-4-咪唑啉-1-基)脂肪酸及其盐和酯，其具有一般式I。这些化合物可用作抗过敏剂、抗哮喘剂等。

  公开号：

  US04349684A1
• 作为产物：
  描述：

  4-苯基-1,3-二氢-2H-咪唑-2-酮 在 sodium hydroxide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.42h， 生成 1-benzyl-5-phenyl-4-imidazolin-2-one
  参考文献：
  名称：

  Regiospecific Functionalization of 1,3-Dihydro-2H-benzimidazol-2-one and Structurally Related Cyclic Urea Derivatives

  摘要：

  Methods for selectively protecting one of the degenerate nitrogen atoms of the cyclic urea derivatives 1,3-dihydro-2H-benzimidazol-2-one (6a), 1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (11), 1,3-dihydro-2H-imidazo[4,5-b]quinolin-2-ones (20), 1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one (22), and 1,3-dihydro-4-phenyl-2H-imidazol-2-one (27) were developed. Heating these cyclic ureas with ethyl 2-pyridyl carbonate in the presence of a base in CH3CN at reflux or DMF at 100 degrees C cleanly provided the monoethoxycarbonyl derivatives 7a, 12, 21, 23, and 28, respectively. Alternatively, treatment of 6a with an excess of diethyl pyrocarbonate or di-tert-butyl dicarbonate afforded the bis-alkoxycarbonyl derivatives 8a and 8b, respectively, which underwent disproportionation to 7a and 7b upon heating with 1 mol equiv of 6a and K2CO3 in CH3CN at reflux. The regiochemistry of the introduction of alkoxycarbonyl groups to benzimidazol-2-one derivatives was not significantly influenced by an electron-withdrawing (CF3, 6b) or an electron-donating (OCH3, 6c) substituent at C-5 of the heterocyclic ring. However, the reaction was found to be sensitive to steric factors since a chlorine substituent ortho to one of the urea N atoms (6e) completely directed the alkoxycarbonyl moiety to the less sterically encumbered N atom, affording a single product (7f, 7g). Alkylation of 7a-g proceeded efficiently to provide products 10a-10ag after removal of the protecting group. Halogenation of monoprotected benzimidazol-2-one 7a occurred regiospecifically to give the monohalo derivatives 7h, 7i, and 7k, the identity of which were readily established from the characteristic chemical shift and spin coupling pattern in their 1H NMR spectra. A protecting group interchange strategy that took advantage of the distinctive chemical reactivities of the EtO(2)C and t-BuO(2)C protecting groups toward isopropylamine was developed that provided access to the isomerically substituted series of monohalo, mono-N-alkylated benzimidazol-2-ones 71 and 7m. The efficient derivatization of the unprotected N atom of these monoprotected cyclic urea derivatives was accomplished by treating with activated and unactivated halides in the. presence of K2CO3 or exposure to alcohols under Mitsunobu conditions. In several cases, mixtures of O- and N-alkylated products were produced which were readily separated by chromatography. Alkylation of 7h with activated halides, using K2CO3 in CH3CN at reflux, occurred without protecting group equilibration; however, a mixture of isomeric alkylated products was obtained when 7h was heated at 110 degrees C in DMF with cyclohexylmethyl bromide in the presence of K2CO3 as the base. Derivatization of 7h under Mitsunobu reaction conditions proceeded with retention of the topological substituent relationships. Subsequent removal of the alkoxycarbonyl moiety afforded monoalkylated cyclic urea derivatives.

  DOI：

  10.1021/jo00111a014

文献信息

• [EN] METHODS AND COMPOSITIONS TO MODIFY GSK-3 ACTIVITY<br/>[FR] PROCÉDÉS ET COMPOSITIONS POUR MODIFIER L'ACTIVITÉ DE GSK-3
  申请人：UNIV OHIO

  公开号：WO2016010611A1

  公开（公告）日：2016-01-21

  Methods for modulating GSK-3 activity and methods for treating a GSK-3 -mediated disorder in a subject in need thereof. The methods include contacting a cell expressing GSK-3 with or administering to the subject in need a therapeutically effective amount of one or more compounds of General Formula (I) or General Formula (II): or pharmaceutically-acceptable salts or solvates thereof.

  调节GSK-3活性的方法和治疗需要的主体中GSK-3介导的疾病的方法。该方法包括将表达GSK-3的细胞与或向需要的主体施用一种或多种通用式(I)或通用式(II)的化合物的治疗有效量接触，或其药用接受的盐或溶剂。
• N-substituted omega-(2-oxo-4-imidazolin-1-yl) alcanoic acids, salts and esters thereof, process for producing the same and these active agents containing pharmaceutical compounds
  申请人：A. Nattermann & Cie. GmbH

  公开号：EP0051829A1

  公开（公告）日：1982-05-19

  the present invention refers to new N-substituted ω-(2-oxo-4-imidazolin-1-yl) alcanoic acids as well as salts and esters thereof having the general formula I process for producing the same and these active agents containing pharmaceutical compounds.

  本发明是指新的 N-取代ω-(2-氧代-4-咪唑啉-1-基)辛酸及其具有通式 I 的盐和酯，以及这些含有药物活性剂的化合物的生产工艺。
• Imidazole and thiazole compositions for modifying biological signaling
  申请人：Ohio University

  公开号：US10023567B2

  公开（公告）日：2018-07-17

  Compounds having General Formula (I) or General Formula (II): in which R1 is chosen from C1 to C10 aliphatic or heteroaliphatic groups, optionally substituted with one or more aryl groups, substituted aryl groups, heteroaryl groups, substituted heteroaryl groups, or combination thereof; R2 is chosen from aromatic moieties, substituted aromatic moieties, heteroaromatic moieties substituted heteroaromatic moieties, and coumarin; R3 is chosen from —H, C1 to C10 aliphatic or heteroaliphatic groups, phenyl, or substituted phenyl, wherein the aliphatic or heteroaliphatic groups are optionally substituted with one or more phenyl groups, aryl groups, heteroaryl groups, substituted heteroaryl groups, or combination thereof, and wherein the aliphatic or heteroaliphatic groups are optionally bonded to R2 to form a ring; X is S or O; and Y is S or NH, may be used in pharmaceutical compositions that modify of biological signaling processes or as reagents for biological assays.

  具有通式(I)或通式(II)的化合物：其中 R1 选自 C1 至 C10 脂肪族或杂脂肪族基团，任选被一个或多个芳基、取代芳基、杂芳基、取代杂芳基或其组合取代；R2 选自芳香族基团、取代芳香族基团、杂芳香族基团、取代杂芳香族基团和香豆素；R3 选自-H、C1 至 C10 脂肪族或杂脂肪族基团、苯基或取代苯基，其中脂肪族或杂脂肪族基团可选择被一个或多个苯基、芳基、杂芳基、取代杂芳基或其组合取代，并且其中脂肪族或杂脂肪族基团可选择与 R2 键合形成环；X 是 S 或 O；Y 是 S 或 NH，可用于改变生物信号转导过程的药物组合物或用作生物检测试剂。
• Prevention and treatment of non-alcoholic fatty liver disease
  申请人：Ohio University

  公开号：US10392381B2

  公开（公告）日：2019-08-27

  Methods for preventing, treating, and/or reducing the risk of developing non-alcoholic fatty liver disease in a subject in need thereof and pharmaceutical compositions for the prevention or treatment of non-alcoholic fatty liver disease. Methods for inhibiting excessive accumulation of fat in liver tissue. The methods include administering to the subject or contacting the liver tissue with a therapeutically effective amount of at least one compound of General Formula (I) or General Formula (II): or pharmaceutically-acceptable salts or solvates thereof. The pharmaceutical composition includes at least one compound of the General Formula (I) or the General Formula (II) for administration to a subject for the prevention or treatment of non-alcoholic fatty liver disease.

  预防、治疗和/或降低有需要者患非酒精性脂肪肝风险的方法，以及预防或治疗非酒精性脂肪肝的药物组合物。抑制脂肪在肝组织中过度积累的方法。这些方法包括向受试者施用或用治疗有效量的至少一种通式（I）或通式（II）化合物：或其药学上可接受的盐或溶解物接触肝组织。药物组合物包括至少一种通式(I)或通式(II)化合物，用于给受试者用药，以预防或治疗非酒精性脂肪肝。
• PREVENTION AND TREATMENT OF NON-ALCOHOLIC FATTY LIVER DISEASE
  申请人：Ohio University

  公开号：US20170196845A1

  公开（公告）日：2017-07-13

  Methods for preventing, treating, and/or reducing the risk of developing non-alcoholic fatty liver disease in a subject in need thereof and pharmaceutical compositions for the prevention or treatment of non-alcoholic fatty liver disease. Methods for inhibiting excessive accumulation of fat in liver tissue. The methods include administering to the subject or contacting the liver tissue with a therapeutically effective amount of at least one compound of General Formula (I) or General Formula (II): or pharmaceutically-acceptable salts or solvates thereof. The pharmaceutical composition includes at least one compound of the General Formula (I) or the General Formula (II) for administration to a subject for the prevention or treatment of non-alcoholic fatty liver disease.