4-(9H-Fluoren-9-yl)butyric acid | 16425-43-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 4-(9H-Fluoren-9-yl)butyric acid
• 英文别名: 4-(9-Fluorenyl)-buttersaeure；4-(9-Fluorenyl)buttersaeure；4-(9H-fluoren-9-yl)butanoic acid
• CAS: 16425-43-7
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: MHAKIVXZQPZQIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(9H-Fluoren-9-yl)butyric acid 在 氢氧化钾 、 对甲苯磺酸 作用下， 生成 9-(2-Methoxycarbonyl-aethyl)-9-(3-methoxycarbonyl-propyl)-fluoren
  参考文献：
  名称：

  Michael reaction of acrylate salts

  摘要：

  DOI：

  10.1021/jo01270a112
• 作为产物：
  描述：

  芴 、 4-bromobutyric acid lithium salt 在 正丁基锂 作用下， 生成 4-(9H-Fluoren-9-yl)butyric acid
  参考文献：
  名称：

  Fluorenylalkanoic and Benzoic Acids as Novel Inhibitors of Cell Adhesion Processes in Leukocytes

  摘要：

  A series of fluoren-9-ylalkanoic and alkylbenzoic acids was prepared as simplified analogues of a previously reported series of antiinflammatory agents which act to inhibit neutrophil recruitment into inflamed tissue. The previous compounds (''leumedins'') contained (alkoxycarbonyl)amino or benzoic acid moieties tethered to a fluorene ring. This functionality was replaced with simple structural elements. The new compounds were, in general, found to be more potent than the earlier series at inhibiting adherence of neutrophils to serum-coated wells or endothelial cells in vitro. Compound 9 was approximately 10-fold more potent than the previously reported FMOC-phenylalanine, of which it is an analogue. Similarly, compound 19 was superior in potency to its first generation progenitor, NPC 16570. The new compounds were shown to inhibit neutrophil adherence under conditions in which adherence is mediated by Mac-1 (CD11b/CD18) and LFA-1 (CD11a/CD18); they thus appear to target beta(2)-integrins in their antiadhesion activity. These compounds provide a departure point for the further development of new cell adhesion inhibitors which should exhibit enhanced potency and a more selective mode of action.

  DOI：

  10.1021/jm00010a009

文献信息

• Fluorenyl derivatives
  申请人：Scios Nova Inc.

  公开号：US05519043A1

  公开（公告）日：1996-05-21

  The compound having the formula: ##STR1## and a method of treating an inflammatory condition comprising administering to an animal in need of such treatment an effective amount of at least one compound represented by the formula.

  该化合物的化学式为：##STR1##，以及一种治疗炎症状况的方法，包括向需要此类治疗的动物施用至少一种由该式所代表的化合物的有效量。
• TODO EISHIRO; YAMAMOTO KAGETOSHI; MURATA ICHIRO, CHEM. LETTERS, 1979, NO 5, 537-540
  作者：TODO EISHIRO、 YAMAMOTO KAGETOSHI、 MURATA ICHIRO

  DOI：——

  日期：——
• US5519043A
  申请人：——

  公开号：US5519043A

  公开（公告）日：1996-05-21
• Michael reaction of acrylate salts
  作者：Henry E. Fritz、David W. Peck、Kenneth E. Atkins

  DOI：10.1021/jo01270a112

  日期：1968.6
• Fluorenylalkanoic and Benzoic Acids as Novel Inhibitors of Cell Adhesion Processes in Leukocytes
  作者：Gregory S. Hamilton、Richard E. Mewshaw、Carmen M. Bryant、Ying Feng、Gerda Endemann、Kip S. Madden、Jennifer E. Danczak、John Perumattam、Lawrence W. Stanton

  DOI：10.1021/jm00010a009

  日期：1995.5

  A series of fluoren-9-ylalkanoic and alkylbenzoic acids was prepared as simplified analogues of a previously reported series of antiinflammatory agents which act to inhibit neutrophil recruitment into inflamed tissue. The previous compounds (''leumedins'') contained (alkoxycarbonyl)amino or benzoic acid moieties tethered to a fluorene ring. This functionality was replaced with simple structural elements. The new compounds were, in general, found to be more potent than the earlier series at inhibiting adherence of neutrophils to serum-coated wells or endothelial cells in vitro. Compound 9 was approximately 10-fold more potent than the previously reported FMOC-phenylalanine, of which it is an analogue. Similarly, compound 19 was superior in potency to its first generation progenitor, NPC 16570. The new compounds were shown to inhibit neutrophil adherence under conditions in which adherence is mediated by Mac-1 (CD11b/CD18) and LFA-1 (CD11a/CD18); they thus appear to target beta(2)-integrins in their antiadhesion activity. These compounds provide a departure point for the further development of new cell adhesion inhibitors which should exhibit enhanced potency and a more selective mode of action.