N-(1-methyl-1,2,3-trihydroxy-2-cyclopentene-4-ylidene)-2-carboxy-pyrrolidinium betaine | 91999-37-0

• 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: N-(1-methyl-1,2,3-trihydroxy-2-cyclopentene-4-ylidene)-2-carboxy-pyrrolidinium betaine
• 英文别名: (2S)-1-(2,4-dihydroxy-4-methyl-3-oxocyclopenten-1-yl)pyrrolidine-2-carboxylic acid
• CAS: 91999-37-0
• 化学式: C₁₁H₁₅NO₅
• 分子量: 241.244
• InChiKey: UPABDZRMCJFZSY-OCAOPBLFSA-N

物化性质

• 沸点：
  482.0±45.0 °C(Predicted)
• 密度：
  1.581±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  98.1
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(1-methyl-1,2,3-trihydroxy-2-cyclopentene-4-ylidene)-2-carboxy-pyrrolidinium betaine 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 1.17h， 生成 3-hydroxy-4-<(E)-(2-furyl)methylidene>methyl-3-cyclopentene-1,2-dione
  参考文献：
  名称：

  Studies on the inhibition of tumor cell growth and microtubule assembly by 3-hydroxy-4-[(E)-(2-furyl)methylidene]methyl-3-cyclopentene-1,2-dione, an intensively coloured Maillard reaction product

  摘要：

  Very recently, 3-hydroxy-4-[(E)-(2-furyl)methylidene]methyl-3-cyclopentene-1,2-dione (1) has been successfully identified as an intensively coloured Maillard product formed from glucose and L-proline upon thermal food processing. Using a biomimetic synthetic strategy, reference material of compound 1 was prepared and purified, and then used to study its effect on the growth of human tumor cells. Compound 1 was found to potently inhibit the growth of human tumor cells in vitro. Using a reporter gene assay we could show that in growth inhibitory concentrations compound 1 effectively inhibits the phosphorylation of the transcription factor Elk-1. In addition, 1 was found to affect the microtubule skeleton. The human mammary carcinoma cell line MCF-7 exhibits a decrease of the microtubule organisation. when treated for 24 h with 1 (greater than or equal to 20 muM). At concentrations of 30 muM and above a loss of microtubule integrity is observed after 1 h incubation. In vitro studies demonstrated that the polymerisation and, to a minor extent, also the depolymerisation of tubulin, isolated and purified from bovine brain, is inhibited in a dose-dependent manner at concentrations of 30 muM and above. This is the first time that a non-enzymatically formed browning compound of known structure was reported to effectively inhibit tumor cell growth and microtubule assembly. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0278-6915(01)00093-x
• 作为产物：
  描述：

  3,4-二羟基-3-己烯-2,5-二酮 、 L-脯氨酸 反应 0.17h， 生成 N-(1-methyl-1,2,3-trihydroxy-2-cyclopentene-4-ylidene)-2-carboxy-pyrrolidinium betaine
  参考文献：
  名称：

  Studies on the inhibition of tumor cell growth and microtubule assembly by 3-hydroxy-4-[(E)-(2-furyl)methylidene]methyl-3-cyclopentene-1,2-dione, an intensively coloured Maillard reaction product

  摘要：

  Very recently, 3-hydroxy-4-[(E)-(2-furyl)methylidene]methyl-3-cyclopentene-1,2-dione (1) has been successfully identified as an intensively coloured Maillard product formed from glucose and L-proline upon thermal food processing. Using a biomimetic synthetic strategy, reference material of compound 1 was prepared and purified, and then used to study its effect on the growth of human tumor cells. Compound 1 was found to potently inhibit the growth of human tumor cells in vitro. Using a reporter gene assay we could show that in growth inhibitory concentrations compound 1 effectively inhibits the phosphorylation of the transcription factor Elk-1. In addition, 1 was found to affect the microtubule skeleton. The human mammary carcinoma cell line MCF-7 exhibits a decrease of the microtubule organisation. when treated for 24 h with 1 (greater than or equal to 20 muM). At concentrations of 30 muM and above a loss of microtubule integrity is observed after 1 h incubation. In vitro studies demonstrated that the polymerisation and, to a minor extent, also the depolymerisation of tubulin, isolated and purified from bovine brain, is inhibited in a dose-dependent manner at concentrations of 30 muM and above. This is the first time that a non-enzymatically formed browning compound of known structure was reported to effectively inhibit tumor cell growth and microtubule assembly. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0278-6915(01)00093-x

文献信息

• Studies on the inhibition of tumor cell growth and microtubule assembly by 3-hydroxy-4-[(E)-(2-furyl)methylidene]methyl-3-cyclopentene-1,2-dione, an intensively coloured Maillard reaction product
  作者：D Marko、M Kemény、E Bernady、M Habermeyer、U Weyand、S Meiers、O Frank、T Hofmann

  DOI：10.1016/s0278-6915(01)00093-x

  日期：2002.1

  Very recently, 3-hydroxy-4-[(E)-(2-furyl)methylidene]methyl-3-cyclopentene-1,2-dione (1) has been successfully identified as an intensively coloured Maillard product formed from glucose and L-proline upon thermal food processing. Using a biomimetic synthetic strategy, reference material of compound 1 was prepared and purified, and then used to study its effect on the growth of human tumor cells. Compound 1 was found to potently inhibit the growth of human tumor cells in vitro. Using a reporter gene assay we could show that in growth inhibitory concentrations compound 1 effectively inhibits the phosphorylation of the transcription factor Elk-1. In addition, 1 was found to affect the microtubule skeleton. The human mammary carcinoma cell line MCF-7 exhibits a decrease of the microtubule organisation. when treated for 24 h with 1 (greater than or equal to 20 muM). At concentrations of 30 muM and above a loss of microtubule integrity is observed after 1 h incubation. In vitro studies demonstrated that the polymerisation and, to a minor extent, also the depolymerisation of tubulin, isolated and purified from bovine brain, is inhibited in a dose-dependent manner at concentrations of 30 muM and above. This is the first time that a non-enzymatically formed browning compound of known structure was reported to effectively inhibit tumor cell growth and microtubule assembly. (C) 2001 Elsevier Science Ltd. All rights reserved.