3-(phenylseleno)propionyl chloride | 113600-04-7

• 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-(phenylseleno)propionyl chloride
• 英文别名: 3-Phenylselanylpropanoyl chloride
• CAS: 113600-04-7
• 化学式: C₉H₉ClOSe
• 分子量: 247.583
• InChiKey: LNHWWYVRYYRTPC-UHFFFAOYSA-N

物化性质

• 沸点：
  303.3±34.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(phenylseleno)propionyl chloride 在 四丁基氟化铵 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.58h， 生成 allyl 2-<(3S,4S)-4-(hydroxymethyl)-2-oxo-3-tritylamino-1-azetidinyl>-3-oxo-5-(phenylseleno)pentanoate
  参考文献：
  名称：

  An examination of O-2-isocephems as orally absorbable antibiotics

  摘要：

  The synthesis and structure-activity relationships of a series of orally absorbed O-2-isocephems are described. These compounds possessed a D-[(p-hydroxyphenyl)glycyl]amino substituent at the 7-position while the substituent at the 3-position was varied. Relative to the analogous cephems, the O-2-isocephems exhibited comparable to better activity against Gram-positive organisms. Against Gram-negative organisms, their activity was variable but did indicate a lower beta-lactamase stability. Following oral administration, the O-2-isocephems generally exhibited longer half-lives but lower Cmax's and urinary recoveries.

  DOI：

  10.1021/jm00401a020
• 作为产物：
  描述：

  3-(phenylselanyl)propanoic acid 在 草酰氯 作用下， 反应 4.0h， 以67%的产率得到3-(phenylseleno)propionyl chloride
  参考文献：
  名称：

  An examination of O-2-isocephems as orally absorbable antibiotics

  摘要：

  The synthesis and structure-activity relationships of a series of orally absorbed O-2-isocephems are described. These compounds possessed a D-[(p-hydroxyphenyl)glycyl]amino substituent at the 7-position while the substituent at the 3-position was varied. Relative to the analogous cephems, the O-2-isocephems exhibited comparable to better activity against Gram-positive organisms. Against Gram-negative organisms, their activity was variable but did indicate a lower beta-lactamase stability. Following oral administration, the O-2-isocephems generally exhibited longer half-lives but lower Cmax's and urinary recoveries.

  DOI：

  10.1021/jm00401a020

文献信息

• Synthesis, Structure−Activity Relationships, and Pharmacokinetic Properties of Dihydroorotate Dehydrogenase Inhibitors:  2-Cyano-3-cyclopropyl-3-hydroxy- <i>N</i>-[3‘-methyl-4‘-(trifluoromethyl)phenyl]propenamide and Related Compounds
  作者：Elizabeth A. Kuo、Philip T. Hambleton、David P. Kay、Phillip L. Evans、Saroop S. Matharu、Edward Little、Neil McDowall、C. Beth Jones、Charles J. R. Hedgecock、Christopher M. Yea、A. W. Edith Chan、Peter W. Hairsine、Ian R. Ager、W. Roger Tully、Richard A. Williamson、Robert Westwood

  DOI：10.1021/jm9604437

  日期：1996.1.1

  been synthesized. Their in vivo biological activity determined in rat and mouse delayed type hypersensitivity has been found to correlate well with their in vitro DHODH potency. The most promising compound (3) has shown activity in rat and mouse collagen (II)-induced arthritis models (ED50 = 2 and 31 mg/kg, respectively) and has shown a shorter half-life in man when compared with leflunomide. Clinical

  新型免疫抑制剂来氟米特（1）的活性代谢物（2）已显示出抑制二氢乳清酸脱氢酶（DHODH）的作用。该酶催化从头进行嘧啶生物合成的第四步。已经合成了一系列活性代谢物2的类似物。已经发现它们在大鼠和小鼠迟发型超敏反应中的体内生物学活性与其体外DHODH效力密切相关。最有希望的化合物（3）在大鼠和小鼠胶原（II）诱导的关节炎模型中显示出活性（分别为ED50 = 2和31 mg / kg），与来氟米特相比，在人中的半衰期更短。类风湿关节炎的临床研究正在进行中。
• MASTALERZ, HAROLD;MENARD, MARCEL;VINET, VIVIANNE;DESIDERIO, JAMES;FUNG-TO+, J. MED. CHEM., 31,(1988) N 6, 1190-1196
  作者：MASTALERZ, HAROLD、MENARD, MARCEL、VINET, VIVIANNE、DESIDERIO, JAMES、FUNG-TO+

  DOI：——

  日期：——