2-(2-naphthacarbonyl)-L-glutamic acid | 116408-47-0

• 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-(2-naphthacarbonyl)-L-glutamic acid
• 英文别名: 2-Naphthoyl glutamic acid；(2S)-2-(naphthalene-2-carbonylamino)pentanedioic acid
• CAS: 116408-47-0
• 化学式: C₁₆H₁₅NO₅
• 分子量: 301.299
• InChiKey: YKNDIAJZDLLIDP-ZDUSSCGKSA-N

物化性质

• 熔点：
  179 °C
• 沸点：
  641.3±45.0 °C(Predicted)
• 密度：
  1.372±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-naphthacarbonyl)-L-glutamic acid 、 L-谷氨酸二乙酯盐酸盐 在 4-二甲氨基吡啶 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以65%的产率得到N-(2-naphthacarbonyl)-1,5-bis(L-glutamic acid diethyl ester)-L-glutamic diamide
  参考文献：
  名称：

  Ultrasound induced formation of organogel from a glutamic dendron

  摘要：

  New L-glutamic acid based dendritic compounds: N-(2-naphthacarbonyl)-L-glutamic acid diethyl ester (NGE) and N-(2-naphthacarbonyl)1,5- bis(L-glutamic acid diethyl ester)-L-glutamic diamide (NBGE) were designed. Although NGE could not form any gels in common solvents, NBGE could form stable gels in hexane, toluene, and water under ultrasound. Three dimensional network structures composed of fibers with various diameters were observed in the gel by SEM and TEM. FTIR spectral measurement revealed that ultrasound during cooling of the solution could destroy some of the hydrogen bond interactions and caused the gel formation. In solution, no CD signal was detected because the naphthyl chromophore is far from the chiral center. In the gel, however, CD signals assigned to the naphthyl group were observed, which indicated that the chirality of the chiral center could be transferred to the chromophore in the supramolecular organogel system. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.070
• 作为产物：
  描述：

  2-萘甲酸 在 sodium hydroxide 、 氯化亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 18.0h， 生成 2-(2-naphthacarbonyl)-L-glutamic acid
  参考文献：
  名称：

  Ultrasound induced formation of organogel from a glutamic dendron

  摘要：

  New L-glutamic acid based dendritic compounds: N-(2-naphthacarbonyl)-L-glutamic acid diethyl ester (NGE) and N-(2-naphthacarbonyl)1,5- bis(L-glutamic acid diethyl ester)-L-glutamic diamide (NBGE) were designed. Although NGE could not form any gels in common solvents, NBGE could form stable gels in hexane, toluene, and water under ultrasound. Three dimensional network structures composed of fibers with various diameters were observed in the gel by SEM and TEM. FTIR spectral measurement revealed that ultrasound during cooling of the solution could destroy some of the hydrogen bond interactions and caused the gel formation. In solution, no CD signal was detected because the naphthyl chromophore is far from the chiral center. In the gel, however, CD signals assigned to the naphthyl group were observed, which indicated that the chirality of the chiral center could be transferred to the chromophore in the supramolecular organogel system. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.070

文献信息

• New derivatives of 5-pentylamino-5-oxopentanoic and
  申请人：Rotta Research Laboratorium S.p.A.

  公开号：US04826878A1

  公开（公告）日：1989-05-02

  New original derivatives are described of 5-pentylamino-5-oxopentanoic and 4-pentylamino-4-oxobutasnoic acids having the formula: ##STR1## in which n is 1 or 2, R.sub.1 is selected from the groups 2-naphthyl, 2 (or 3)-quinolinyl, 2 (or 3)-indolyl, 2 (or 3)-benzofuranyl, 2 (or 3)-benzothiophenyl, and R.sub.2 is a pentyl group or an alkoxyalkyl group with 4 or 5 carbon atoms, preferably pentyl, 2-ethoxyethyl, 3-methoxypropyl or 3-ethoxypropyl. The compounds have a powerful antagonistic activity towards cholecystokinin and are particularly useful in the treatment of illnesses of the digestive system, such as colitis, biliary diskinesia, pancreatitis or in the treatment of disorders of the central nervous system imputable to deficiencies in the physiological neuron levels of cholecystokinin or other related bioactive polypeptides.

  本文介绍了5-戊基氨基-5-氧代戊酸和4-戊基氨基-4-氧代丁酸的新原始衍生物，其化学式为：##STR1## 其中n为1或2，R.sub.1选自2-萘基，2（或3）-喹啉基，2（或3）-吲哚基，2（或3）-苯并呋喃基，2（或3）-苯并噻吩基，R.sub.2为戊基或具有4或5个碳原子的烷氧基烷基，优选为戊基，2-乙氧基乙基，3-甲氧基丙基或3-乙氧基丙基。这些化合物具有强大的胆囊收缩素拮抗活性，特别适用于治疗消化系统疾病，如结肠炎，胆道运动障碍，胰腺炎或由于胆囊收缩素或其他相关生物活性多肽生理神经元水平不足引起的中枢神经系统疾病的治疗。
• Derivatives of 5-pentylamino-5-oxopentanoil and
  申请人：Rotta Research Laboratorium

  公开号：US04891381A1

  公开（公告）日：1990-01-02

  New original derivatives are described of 5-pentylamino -5-oxopentanoic and 4-pentylamino-4-oxobutanoic acids having the formula: ##STR1## in which n is 1 or 2, R.sub.1 is selected from the groups 2-naphthyl, 2 (or 3)-quinolinyl, 2 (or 3)-indolyl, 2 (or 3)-benzofuranyl, 2 (or 3)-benzothiophenyl, and R.sub.2 is a pentyl group or an alkoxyalkyl group with 4 or 5 carbon atoms, preferably pentyl, 2-ethoxyethyl, 3-methoxypropyl or 3-ethoxypropyl. The compounds have a powerful antagonistic activity towards cholecystokinin and are particularly useful in the treatment of illnesses of the digestive system, such as colitis, biliary diskinesia, pancreatitis or in the treatment of disorders of the central nervous system imputable to deficiencies in the physiological neuron levels of cholecystokinin or other related bioactive polypeptides.

  本文介绍了5-戊基氨基-5-氧代戊酸和4-戊基氨基-4-氧代丁酸的新原始衍生物，其化学式为：##STR1## 其中n为1或2，R.sub.1选自2-萘基，2（或3）-喹啉基，2（或3）-吲哚基，2（或3）-苯并呋喃基，2（或3）-苯并噻吩基，R.sub.2为戊基或具有4或5个碳原子的烷氧基烷基，优选为戊基，2-乙氧基乙基，3-甲氧基丙基或3-乙氧基丙基。这些化合物对胆囊收缩素具有强大的拮抗作用，特别适用于治疗消化系统疾病，如结肠炎，胆道运动障碍，胰腺炎或由于胆囊收缩素或其他相关生物活性多肽的生理神经元水平不足引起的中枢神经系统疾病的治疗。
• New Derivatives of 5-pentylamino-5-oxopentanoic and 4-pentylamino-4-oxo-butanoic acids with antagonistic activity towards cholecystokinin and a method for their preparation
  申请人：ROTTA RESEARCH LABORATORIUM S.P.A.

  公开号：EP0272228B1

  公开（公告）日：1992-02-05
• US4826878A
  申请人：——

  公开号：US4826878A

  公开（公告）日：1989-05-02
• US4891381A
  申请人：——

  公开号：US4891381A

  公开（公告）日：1990-01-02