(3RS)-2-氧代-4-苯基-3-(苯基羰基)氨基-1,1,1-三氟丁烷 | 106745-98-6

• 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: (3RS)-2-氧代-4-苯基-3-(苯基羰基)氨基-1,1,1-三氟丁烷
• 英文名称: (3RS)-2-oxo-4-phenyl-3-(phenylcarbonyl)amino-1,1,1-trifluorobutane
• 英文别名: N-<3,3,3-trifluoro-2-oxo-1-(phenylmethyl)propyl>benzamide；benzohydroxamic acid；1,1,1-trifluoro-2-one-3-benzoylamino-4-phenylbutane；N-(3,3,3-trifluoro-2-oxo-1-(phenylmethyl)propyl)benzamide；N-[3,3,3-trifluoro-2-oxo-1-(phenylmethyl)propyl]benzamide；(3RS)-3-Benzoylamino-2-oxo-4-phenyl-1,1,1-trifluorobutane；N-(4,4,4-trifluoro-3-oxo-1-phenylbutan-2-yl)benzamide
• CAS: 106745-98-6
• 化学式: C₁₇H₁₄F₃NO₂
• 分子量: 321.299
• InChiKey: SKVHYWXIGYJDFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3RS)-2-氧代-4-苯基-3-(苯基羰基)氨基-1,1,1-三氟丁烷 在 盐酸 作用下， 生成 4,4,4-trifluoro-3-hydroxy-1-phenylbutan-2-one
  参考文献：
  名称：

  Synthesis of peptidyl fluoromethyl ketones and peptidyl .alpha.-keto esters as inhibitors of porcine pancreatic elastase, human neutrophil elastase, and rat and human neutrophil cathepsin G

  摘要：

  Comparison of MeO-Suc-Val-Pro-Phe-CO2Me (29) and MeO-Suc-Ala-Ala-Pro-Phe- CO2Me (25) with their corresponding trifluoromethyl ketones 9a and 9b, respectively, in rat and human neutrophil cathepsin G assays showed the alpha-keto esters to be more potent inhibitors. Likewise, Ac-Pro-Ala-Pro-Ala-CO2Me (21) was more potent than its corresponding trifluoromethyl ketone (9c) in both porcine pancreatic elastase and human neutrophil elastase assays. Within a set of Ala-Ala-Pro-Val-CF3 elastase inhibitors, the carbobenzyloxy (Cbz) N-protecting group conferred greater potency as a P5 site recognition unit for elastase than did dansyl, methoxysuccinyl, or tert-butyloxycarbonyl. Initial inhibition of elastase was greater when trifluoromethyl ketone 9f was added from a stock solution of dimethyl sulfoxide than when it had been buffer-equilibrated prior to assay, which suggests that the nonhydrated ketone is the more effective form of the inhibitor. The most potent elastase inhibitor we report is Na-(Ad-SO2)-N epsilon-(MeO-Suc)Lys-Pro-Val-CF3 (16) which has a Ki of 0.58 nM.

  DOI：

  10.1021/jm00163a063
• 作为产物：
  描述：

  4-苄基-2-苯基-2-噁唑啉-5-酮 在 草酸 作用下， 反应 0.25h， 生成 (3RS)-2-氧代-4-苯基-3-(苯基羰基)氨基-1,1,1-三氟丁烷
  参考文献：
  名称：

  氟化α-氨基酮的合成第一部分：α-苯甲酰胺基烷基二氟和三氟甲基酮

  摘要：

  由α-氨基酸制得的2-苯基-5（4H）-恶唑酮通过改良的Dakin-West方法与二氟和三氟乙酸酐反应，以一锅法反应生成α-苯甲酰胺基烷基二氟和三氟甲基酮收率高。单氟甲基类似物也由α-氨基酸制备，但是避免了使用剧毒的氟乙酸酐。关键步骤是在相应的溴甲基酮上进行卤素交换反应。

  DOI：

  10.1016/s0040-4039(00)84319-1

文献信息

• Thiazolidine derivatives
  申请人：Santen Pharmaceutical Co., Ltd.

  公开号：US06410576B1

  公开（公告）日：2002-06-25

  An object of the present invention is to provide novel thiazolidine derivatives which are useful as drugs. The thiazolidine derivatives according to the present invention are compounds represented by the following general formula [I] and salts thereof, wherein R1 is alkyl, hydroxy, alkoxy, alkoxyalkyl, phenyl, phenylalkyl, phenylalkoxy, phenoxy, phenoxyalkyl, amino, alkylamino or a nonaromatic heterocycle; R2 is H or alkyl; R3 is H, alkyl or phenyl; R4 is H or alkyl; R5 is alkyl, halogenoalkyl, hydroxy, alkoxy, phenyl, phenylalkoxy, phenoxy, carboxyl, alkoxycarbonyl, phenylalkoxycarbonyl or an aromatic heterocycle; A1 is alkylene; and A2 is alkylene.

  本发明的一个目的是提供作为药物有用的新型噻唑烷衍生物。根据本发明的噻唑烷衍生物是由以下一般式[I]表示的化合物及其盐， 其中R1是烷基、羟基、烷氧基、烷氧基烷基、苯基、苯基烷基、苯基烷氧基、苯氧基、苯氧基烷基、氨基、烷基氨基或非芳香杂环；R2是H或烷基；R3是H、烷基或苯基；R4是H或烷基；R5是烷基、卤代烷基、羟基、烷氧基、苯基、苯基烷氧基、苯氧基、羧基、烷氧羰基、苯基烷氧羰基或芳香杂环；A1是烷基；A2是烷基。
• Inhibitors of Cathepsin G and elastase for preventing connective tissue
  申请人：Merrell Pharmaceuticals Inc.

  公开号：US05510333A1

  公开（公告）日：1996-04-23

  Novel compounds which are chemically linked inhibitors of the proteases Elastase and Cathepsin G prevent connective tissue degradation associated with neutrophil induced inflammatory disease.

  新化合物，它们是与蛋白酶弹性蛋白酶和猫hepsin G化学连接的抑制剂，可以预防与中性粒细胞诱导的炎症性疾病相关的结缔组织降解。
• Assays, methods and means
  申请人：Maxwell Patrick Henry

  公开号：US20100272726A1

  公开（公告）日：2010-10-28

  A novel class of hydroxylases is described having the amino acid sequence of SEQ ID NO: 2, 4, 6 and 8, and variants and fragments thereof having HIF hydroxylation activity. The polypeptides of the invention have in particular prolyl hydroxylase activity. An assay method monitors the interaction of the HIF hydroxylase with a substrate. Modulators of HIF hydroxylase are provided for use in the treatment of a condition associated with increased or decreased HIF levels or activity or for the treatment of a condition where it is desirable to modulate HIF levels or activity.

  本文描述了一种新型的羟化酶，其氨基酸序列为SEQ ID NO：2、4、6和8，以及具有HIF羟化活性的变体和片段。本发明的多肽特别具有脯氨酸羟化酶活性。一种测定方法监测HIF羟化酶与底物的相互作用。提供了HIF羟化酶的调节剂，用于治疗与HIF水平或活性增加或减少相关的疾病，或用于治疗需要调节HIF水平或活性的疾病。
• Assays, Methods and Means
  申请人：Isis Innovation Limited

  公开号：US20140294842A1

  公开（公告）日：2014-10-02

  A novel class of hydroxylases is described having the amino acid sequence of SEQ ID No. 2, 4, 6 and 8, and variants and fragments thereof having HIF hydroxylation activity. The polypeptides of the invention have in particular prolyl hydroxylase activity. An assay method monitors the interaction of the HIF hydroxylase with a substrate. Modulators of HIF hydroxylase are provided for use in the treatment of a condition associated with increased or decreased HIF levels or activity or for the treatment of a condition where it is desirable to modulate HIF levels or activity.

  本文介绍了一类新型羟化酶，其氨基酸序列为SEQ ID No. 2、4、6和8及其变异体和片段，具有HIF羟化活性。本发明的多肽特别具有脯氨酸羟化酶活性。一种检测方法监测HIF羟化酶与底物的相互作用。提供用于治疗与HIF水平或活性增加或减少有关的疾病或治疗需要调节HIF水平或活性的疾病的HIF羟化酶调节剂。
• Novel thiazine derivatives
  申请人：SANTEN PHARMACEUTICAL CO.,LTD.

  公开号：US20040097496A1

  公开（公告）日：2004-05-20

  A compound having 3-oxo-3,4-dihydro-2H-1,4-thiazine 4-tetrahydropyrazine as a main skeleton. The compound is a chymase inhibitor and is represented by the following formula [I] and salts thereof: 1 In the formula [I], X is S; R 1 and R 2 are H, alkyl, cycloalkyl or aryl; R 3 and R 4 are H, alkyl, cycloalkyl, aryl or an aromatic heterocycle; R 5 is H, alkyl, cycloalkyl, aryl or -A 3 -A 4 -R 7 ; R 6 is H, alkyl, cycloalkyl, hydroxy, alkoxy, aryl, aryloxy or an aromatic heterocycle; R 7 is H, alkyl, hydroxy, alkoxy, aryl, aryloxy, amino, alkylamino, arylamino, an aromatic heterocycle or a nonaromatic heterocycle; A 1 is alkylene; A 2 is carbonyl or sulfonyl; A 3 is alkylene; A 4 is carbonyl or oxalyl; and n is 0 or 1.

  化合物具有3-氧代-3,4-二氢-2H-1,4-噻嗪-4-四氢吡嗪作为主要骨架。该化合物是一种Chymase抑制剂，由以下公式[I]及其盐所表示：1在公式[I]中，X为S；R1和R2为H，烷基，环烷基或芳基；R3和R4为H，烷基，环烷基，芳基或芳香族杂环；R5为H，烷基，环烷基，芳基或-A3-A4-R7；R6为H，烷基，环烷基，羟基，烷氧基，芳基，芳氧基或芳香族杂环；R7为H，烷基，羟基，烷氧基，芳基，芳氧基，氨基，烷基氨基，芳基氨基，芳香族杂环或非芳香族杂环；A1为烷基；A2为羰基或磺酰基；A3为烷基；A4为羰基或草酰基；n为0或1。