2-(3-(2-hydroxyethyl)benzyl)-3-isobutoxycyclopent-2-enone | 1333144-89-0

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 2-(3-(2-hydroxyethyl)benzyl)-3-isobutoxycyclopent-2-enone
• 英文别名: 2-[[3-(2-hydroxyethyl)phenyl]methyl]-3-(2-methylpropoxy)cyclopent-2-en-1-one
• CAS: 1333144-89-0
• 化学式: C₁₈H₂₄O₃
• 分子量: 288.387
• InChiKey: ATUZFFSRRKMKEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-(2-hydroxyethyl)benzyl)-3-isobutoxycyclopent-2-enone 在 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.5h， 生成 4-chloro-N-(3-((2-isobutoxy-5-oxocyclopent-1-en-1-yl)methyl)phenethyl)benzenesulfonamide
  参考文献：
  名称：

  Cyclopentane-1,3-dione: A Novel Isostere for the Carboxylic Acid Functional Group. Application to the Design of Potent Thromboxane (A2) Receptor Antagonists

  摘要：

  Cyclopentane-1,3-diones are known to exhibit pK(a) values typically in the range of carboxylic acids. To explore the potential of the cyclopentane-1,3-dione unit as a carboxylic acid isostere, the physical chemical properties of representative congeners were examined and compared with similar derivatives bearing carboxylic acid or tetrazole residues. These studies suggest that cyclopentane-1,3-diones may effectively substitute for the carboxylic acid functional group. To demonstrate the use of the cyclopentane-1,3-dione isostere in drug design, derivatives of a known thromboxane A(2) prostanoid (TP) receptor antagonist, 3-(3-(2-(4-chlorophenylsulfonamido)ethyl)phenyl)propanoic acid (12), were synthesized and evaluated in both functional and radioligand-binding assays. A series of mono- and disubstituted cyclopentane-1,3-dione derivatives (41-45) were identified that exhibit nanomolar IC50 and K-d values similar to 12. Collectively, these studies demonstrate that the cyclopentane-1,3-dione moiety comprises a novel isostere of the carboxylic acid functional group. Given the combination of the relatively strong acidity, tunable lipophilicity, and versatility of the structure, the cyclopentane-1,3-dione moiety may constitute a valuable addition to the palette of carboxylic acid isosteres.

  DOI：

  10.1021/jm200980u
• 作为产物：
  描述：

  3-(2-羟基乙基)苯甲醛 在 咪唑 、 二氢吡啶 、 对甲苯磺酸 、 L-脯氨酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 27.0h， 生成 2-(3-(2-hydroxyethyl)benzyl)-3-isobutoxycyclopent-2-enone
  参考文献：
  名称：

  Cycloalkyl-dione Derivatives And Methods Of Their Use

  摘要：

  本发明涉及以下式I的化合物：其中A为0、1或2；m为0或1；R1为H或C1-6烷基，R2为H、C1-6烷基、取代或未取代芳基，或取代或未取代杂环芳基；X为O或N；以及它们的互变异构体和药学上可接受的盐形式。还描述了这些化合物的用途。

  公开号：

  US20120329877A1

文献信息

• Cycloalkyl-dione derivatives and methods of their use
  申请人：Atasoylu Onur

  公开号：US08530520B2

  公开（公告）日：2013-09-10

  The present invention is directed to carboxylic acid-containing pharmaceutical compounds where the carboxylic acid moieties have been substituted with cycloalkyl-dione derivatives, as well as tautomers and pharmaceutically acceptable salt forms thereof. These bioisosteric replacements improve the compound's ability to effectively cross the blood brain barrier and result in improved pharmacokinetic, toxicological, and/or safety profiles.

  本发明涉及含有羧酸的药物化合物，其中羧酸基团已被环烷二酮衍生物取代，以及它们的互变异构体和药学上可接受的盐形式。这些生物同位素替代物提高了化合物有效穿过血脑屏障的能力，并导致改善的药代动力学、毒理学和/或安全性能。
• US8530520B2
  申请人：——

  公开号：US8530520B2

  公开（公告）日：2013-09-10