(2S,1R)-2-(2,5-difluorophenoxy)-1-phenylprop-2-ylamine

• 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: (2S,1R)-2-(2,5-difluorophenoxy)-1-phenylprop-2-ylamine
• 英文别名: (1R,2S)-2-(2,5-difluorophenoxy)-1-phenylpropan-1-amine
• 化学式: C₁₅H₁₅F₂NO
• 分子量: 263.287
• InChiKey: JBMJGTORQAQZTN-BONVTDFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  35.25
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  左旋去甲麻黄碱 在 盐酸 、 potassium tert-butylate 、 三乙胺 作用下， 以 四氯化碳 为溶剂， 生成 (2S,1R)-2-(2,5-difluorophenoxy)-1-phenylprop-2-ylamine
  参考文献：
  名称：

  鞘氨醇脱水酶抑制剂作为稻瘟病杀菌剂的设计：去氧麻黄碱的衍生物。

  摘要：

  与不同抑制剂复合的大麦醇式脱水酶的五个X射线晶体结构已描绘了结合袋的构象柔性区。该信息用于设计和合成去甲肾上腺素衍生的氰基乙酰胺类抑制剂，从而产生有效的杀菌剂。

  DOI：

  10.1016/s0960-894x(99)00247-4

文献信息

• Design of Inhibitors of Scytalone Dehydratase: Probing Interactions with an Asparagine Carboxamide
  作者：Gregory S Basarab、Douglas B Jordan、Troy C Gehret、Rand S Schwartz

  DOI：10.1016/s0968-0896(02)00272-9

  日期：2002.12

  Among the active-site residues of scytalone dehydratase, the side-chain carboxamide of asparagine 131 has the greatest potential for strong electrostatic interactions. Structure-based inhibitor design aimed at enhancing interactions with this residue led to the synthesis of a series of highly potent inhibitors that have a five- or six-membered ring containing a carbonyl functionality for hydrogen bonding. To achieve a good orientation for hydrogen bonding, the inhibitors incorporate a phenyl substituent that displaces a phenylalanine residue away from the five- or six-membered rings. Without the phenyl substituent, inhibitor binding potency is diminished by three orders of magnitude. Larger K, values of a site-directed mutant (Asn131Ala) of scytalone dehydratase in comparison to those of wild-type enzyme validate the design concept. The most potent inhibitor (K-i = 15 pM) contains a tetrahydrothiophenone that can form a single hydrogen bond with the asparagine carboxamide. Inhibitors with a butyrolactam that can form two hydrogen bonds with the asparagine carboxamide demonstrate excellent in vivo fungicidal activity. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Design of scytalone dehydratase inhibitors as rice blast fungicides: Derivatives of norephedrine
  作者：Gregory S. Basarab、Douglas B. Jordan、Troy C. Gehret、Rand S. Schwartz、Zdzislaw Wawrzak

  DOI：10.1016/s0960-894x(99)00247-4

  日期：1999.6

  Five X-ray crystal structures of scytalone dehydratase complexed with different inhibitors have delineated conformationally flexible regions of the binding pocket. This information was used for the design and synthesis of a norephedrine-derived cyanoacetamide class of inhibitors leading to potent fungicides.

  与不同抑制剂复合的大麦醇式脱水酶的五个X射线晶体结构已描绘了结合袋的构象柔性区。该信息用于设计和合成去甲肾上腺素衍生的氰基乙酰胺类抑制剂，从而产生有效的杀菌剂。