2-carbamoylcyclopentanecarboxylic acid | 40482-10-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-carbamoylcyclopentanecarboxylic acid
• 英文别名: (+/-)-cis-2-carbamoyl-cyclopentanecarboxylic acid；(+/-)-cis-2-Carbamoyl-cyclopentancarbonsaeure；rel-(1R,2S)-2-(Aminocarbonyl)cyclopentanecarboxylic acid；(1S,2R)-2-carbamoylcyclopentane-1-carboxylic acid
• CAS: 40482-10-8
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: UJJTVJUZAUYKDH-UHNVWZDZSA-N

物化性质

• 沸点：
  426.4±34.0 °C(Predicted)
• 密度：
  1.316±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-carbamoylcyclopentanecarboxylic acid 在 吡啶 、 苯磺酰氯 作用下， 以 乙醚 为溶剂， 生成 1,3-diphenyl-2,4,5,6-tetrahydrocyclopenta[c]pyrrole
  参考文献：
  名称：

  1,3-Diaryl-4,5,6,7-tetrahydro-2H-isoindole Derivatives:  A New Series of Potent and Selective COX-2 Inhibitors in Which a Sulfonyl Group Is Not a Structural Requisite

  摘要：

  Novel tetrahydro-2H-isoindoles have been prepared and evaluated as inhibitors of the COX-2 isoenzyme. A 1,S-diaryl substitution on the central polycyclic ring system and absence of a sulfonyl moiety are the two structural features of this chemical series. A short and easy synthetic pathway produced several derivatives which were shown to be potent and selective COX-2 vs COX-1 inhibitors (IC50 = 0.6-100 nM for COX-2, 100->1000 nM for COX-1). Structural modifications established that a bicyclic ring appended to the pyrrole nucleus and 4,4'-difluoro substitution on the phenyl rings were optimal for high inhibitory potency. Activity was confirmed in the human whole blood assay and subsequently in the murine air-pouch model in which in vivo PGE2 inhibitory activity was evaluated with respect to gastric tolerance (ED50 for inhibition of exudate PGE2 of 3 mg/kg and gastric PGEB of 20 mg/kg). Gastric tolerance was further assessed after administration to mice of high doses (up to 400 mg/kg) of the inhibitors by measurement of gastric damage. This panel of studies allowed selection of a number of tetrahydro-2H-isoindoles which were compared in the adjuvant-induced arthritis model. Compounds 32 and 37 showed the most potent activity with ED50 values for edema inhibition in the noninjected paw of 0.35 and 0.15 mg/kg/day, respectively, after oral administration. In addition, this interesting antiinflammatory profile was accompanied by a protective effect against arthritis-induced osteopenia, the decrease being 50% with a dose of 0.25 mg/kg/day.

  DOI：

  10.1021/jm990965x
• 作为产物：
  描述：

  cyclopentane-cis-1,2-dicarboxylic acid anhydride 在 ammonium hydroxide 作用下， 以100%的产率得到2-carbamoylcyclopentanecarboxylic acid
  参考文献：
  名称：

  1,3-Diaryl-4,5,6,7-tetrahydro-2H-isoindole Derivatives:  A New Series of Potent and Selective COX-2 Inhibitors in Which a Sulfonyl Group Is Not a Structural Requisite

  摘要：

  Novel tetrahydro-2H-isoindoles have been prepared and evaluated as inhibitors of the COX-2 isoenzyme. A 1,S-diaryl substitution on the central polycyclic ring system and absence of a sulfonyl moiety are the two structural features of this chemical series. A short and easy synthetic pathway produced several derivatives which were shown to be potent and selective COX-2 vs COX-1 inhibitors (IC50 = 0.6-100 nM for COX-2, 100->1000 nM for COX-1). Structural modifications established that a bicyclic ring appended to the pyrrole nucleus and 4,4'-difluoro substitution on the phenyl rings were optimal for high inhibitory potency. Activity was confirmed in the human whole blood assay and subsequently in the murine air-pouch model in which in vivo PGE2 inhibitory activity was evaluated with respect to gastric tolerance (ED50 for inhibition of exudate PGE2 of 3 mg/kg and gastric PGEB of 20 mg/kg). Gastric tolerance was further assessed after administration to mice of high doses (up to 400 mg/kg) of the inhibitors by measurement of gastric damage. This panel of studies allowed selection of a number of tetrahydro-2H-isoindoles which were compared in the adjuvant-induced arthritis model. Compounds 32 and 37 showed the most potent activity with ED50 values for edema inhibition in the noninjected paw of 0.35 and 0.15 mg/kg/day, respectively, after oral administration. In addition, this interesting antiinflammatory profile was accompanied by a protective effect against arthritis-induced osteopenia, the decrease being 50% with a dose of 0.25 mg/kg/day.

  DOI：

  10.1021/jm990965x

文献信息

• Dolastatin 15 derivatives
  申请人：BASF Aktiengesellschaft

  公开号：US20010018422A1

  公开（公告）日：2001-08-30

  Compounds of the present invention include cell growth inhibitors which are peptides of Formula I A-B-D-E-F-G (I) and acid salts thereof, wherein A, D, and E are &agr;-amino acid residues, B is an &agr;-amino acid residue or an &agr;-hydroxy acid residue, F is an aminobenzoic acid residue or an aminocycloalkanecarboxylic acid residue, and G is a monovalent radical, such as, for example, a hydrogen atom, an amino group, an alkyl group, an alkylene alkyl ether, an alkylene alkyl thioether, an alkylene aldehyde, an alkylene amide, a &bgr;-hydroxylamino group, a hydrazido group, an alkoxy group, a thioalkoxy group, an aminoxy group, an oximato group, an alkylene aryl group, an alkylene ester, an alkylene sultoxide or an alkylene sulfone. Another aspect of the present invention includes pharmaceutical compositions comprising a compound of Formula I and a pharmaceutically acceptable carrier. An additional embodiment of the present invention is a method for treating cancer in a mammal, such as a human, comprising administering to the mammal an effective amount of a compound of Formula I in a pharmaceutically acceptable composition.

  本发明的化合物包括细胞生长抑制剂，其为公式IA-B-D-E-F-G（I）及其酸盐的肽，其中A、D和E为α-氨基酸残基，B为α-氨基酸残基或α-羟基酸残基，F为氨基苯甲酸残基或氨基环烷基羧酸残基，G为单价基团，例如氢原子，氨基团，烷基，烷基乙醚，烷基硫醚，烷基醛，烷基酰胺，β-羟基氨基团，肼基，烷氧基，硫代烷氧基，氨氧基，肟基，烷基芳基基团，烷基酯，烷基磺酸酯或烷基磺酸酰。本发明的另一个方面包括含有公式I化合物和药学上可接受的载体的制药组合物。本发明的另一个实施例是一种治疗哺乳动物，例如人类癌症的方法，包括向哺乳动物内部注射药学上可接受的公式I化合物的有效量。
• Plieninger; Schneider, Chemische Berichte, 1959, vol. 92, p. 1594,1598
  作者：Plieninger、Schneider

  DOI：——

  日期：——
• DOLASTATIN 15 DERIVATIVES
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：EP1093460A1

  公开（公告）日：2001-04-25
• US5962724A
  申请人：——

  公开号：US5962724A

  公开（公告）日：1999-10-05
• US5985837A
  申请人：——

  公开号：US5985837A

  公开（公告）日：1999-11-16