5-bromomethylene-4-ethyl-3-methyl-2-oxo-2,5-dihydropyrrole | 57097-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 5-bromomethylene-4-ethyl-3-methyl-2-oxo-2,5-dihydropyrrole
• 英文别名: 5-bromomethylene-4-ethyl-3-methyl-2-oxo-1H-pyrrole；(5E)-5-(bromomethylidene)-4-ethyl-3-methylpyrrol-2-one
• CAS: 57097-09-3；65113-79-3
• 化学式: C₈H₁₀BrNO
• 分子量: 216.077
• InChiKey: XXZDLRVNVRDLQF-QPJJXVBHSA-N

物化性质

• 熔点：
  138-139 °C
• 沸点：
  308.1±42.0 °C(Predicted)
• 密度：
  1.521±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-bromomethylene-4-ethyl-3-methyl-2-oxo-2,5-dihydropyrrole 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 19.5h， 生成 <8³-13C>-xanthobilirubic acid
  参考文献：
  名称：

  13种CO 2 H标记的单和双吡咯羧酸的合成和酸度常数。来自13 C-NMR的pK a

  摘要：

  制备了六种在CO 2 H基团中高度富集13 C的单羧酸，并在H 2 O和H 2 O-（CD 3）2中以低浓度10 -4 -10 -5 M的pK a值进行了测定。通过分析pH依赖性13 CO 2 H NMR化学位移分析SO混合物。CO的变化的曲线图2 H（CO 2 - ）13 C-NMR化学位移VS pH值，得到一个典型的滴定曲线从其中的pK一个的对[1- 13C] -phenylpropionic（1）和[1- 13 C] -phenylacetic（2测定）的酸为4.60和H中分别4.16 2 O，和4.67和4.31分别H中2 -O-27％（体积）（CD 3）2 SO。经测定，在H 2 O-27％vol（CD 3）2 SO中，胆红素类似物，黄胆红酸（5）和去黄胆红酸（6）的pK a值分别为4.76和4.64 ，并推断为pK a值〜 H 2 O中为4.62和4.51 。

  DOI：

  10.1016/0040-4020(94)01052-2

文献信息

• Compositions and methods for increasing the sensitivity of apoptosis-resistant tumor cells to inducers of apoptosis
  申请人：——

  公开号：US20030207933A1

  公开（公告）日：2003-11-06

  Disclosed herein are novel compositions and methods for the treatment of cancer and other diseases. More particularly, the present invention provides compositions and methods for reversing the resistance and increasing the sensitivity of apoptosis-resistant cells to all forms of cancer therapies, such as radiation and chemotherapy, for the treatment of apoptosis-resistant cancers.

  本文披露了治疗癌症和其他疾病的新型组合物和方法。更具体地说，本发明提供了组合物和方法，用于逆转抗凋亡细胞对所有形式的癌症治疗（如放疗和化疗）的耐药性，并增加其对治疗抗凋亡癌症的敏感性。
• A Water-Soluble Synthetic Bilirubin with Carboxyl Groups Replaced by Sulfonyl Moieties
  作者：Stefan E. Boiadjiev、David A. Lightner

  DOI：10.1007/s007060170035

  日期：2001.10

  The first symmetrical bilirubin analog with CO2H groups replaced by SO3H, 8,12-bis-(2-sulfo-ethyl)-3,17-diethyl-2,7,13,18-tetramethyl-(10H,21H,23H,24H)-bilin-1,19-dione, was synthesized from methyl (2,4-dimethyl-5-ethoxycarbonyl-1H-pyrrol-3-yl) acetate in nine steps via the sulfonic acid analog of xanthobilirubic acid (XBR) and isolated as its disodium salt. The sulfonic acid group was introduced at an early stage of the synthesis by reaction of an intermediate, ethyl 4-(2-bromoethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate, with sodium sulfite. The disodium bilirubin disulfonate exhibits NMR spectroscopic properties rather similar to those of the parent carboxylic acid, mesobilirubin-XIII alpha; however, its UV/Vis spectra are blue-shifted and broadened relative to those of the parent compound. Like mesobilirubin, the disulfonate displays-a positive exciton chirality circular dichroism spectrum, albeit with weaker Cotton effects, in a buffered aqueous solution (pH = 7.4) containing a 2:1 molar ratio of human serum albumin.
• [EN] COMPOSITIONS AND METHODS FOR INCREASING THE SENSITIVITY OF APOPTOSIS-RESISTANT TUMOR CELLS TO INDUCERS OF APOPTOSIS<br/>[FR] COMPOSITIONS ET PROCEDES POUR ACCROITRE LA SENSIBILITE DE CELLULES TUMORALES RESISTANTES A L'APOPTOSE A DES INDUCTEURS D'APOPTOSE
  申请人：PANORAMA RES INC

  公开号：WO2004069209A2

  公开（公告）日：2004-08-19

  Disclosed herein are novel compositions and methods for the treatment of cancer and other diseases. More particularly, the present invention provides compositions and methods for reversing the resistance and increasing the sensitivity of apoptosis-resistance cells to all forms of cancer therapies, such as radiation and chemotherapy, for the treatment of apoptosis-resistance cancers.
• Synthesis and acidity constants of 13CO2H-labelled mono and dipyrrole carboxylic acids. pKa from 13C-NMR
  作者：Darren L. Holmes、David A. Lightner

  DOI：10.1016/0040-4020(94)01052-2

  日期：1995.2

  [1-13C]-phenylacetic (2) acids were determined to be 4.60 and 4.16 respectively in H2O, and 4.67 and 4.31 respectively in H2O-27% vol (CD3)2SO. Bilirubin analogs, xanthobilirubic acid (5) and nor-xanthobilirubic acid (6) were determined to have pKa values of 4.76 and 4.64 respectively in H2O-27% vol (CD3)2SO, and extrapolated to pKa values ∼4.62 and 4.51 in H2O.

  制备了六种在CO 2 H基团中高度富集13 C的单羧酸，并在H 2 O和H 2 O-（CD 3）2中以低浓度10 -4 -10 -5 M的pK a值进行了测定。通过分析pH依赖性13 CO 2 H NMR化学位移分析SO混合物。CO的变化的曲线图2 H（CO 2 - ）13 C-NMR化学位移VS pH值，得到一个典型的滴定曲线从其中的pK一个的对[1- 13C] -phenylpropionic（1）和[1- 13 C] -phenylacetic（2测定）的酸为4.60和H中分别4.16 2 O，和4.67和4.31分别H中2 -O-27％（体积）（CD 3）2 SO。经测定，在H 2 O-27％vol（CD 3）2 SO中，胆红素类似物，黄胆红酸（5）和去黄胆红酸（6）的pK a值分别为4.76和4.64 ，并推断为pK a值〜 H 2 O中为4.62和4.51 。