1-<4-(2-N-aziridylethoxy)phenyl>-1,2-diphenyl-2-iodoethylene | 113202-47-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-<4-(2-N-aziridylethoxy)phenyl>-1,2-diphenyl-2-iodoethylene
• 英文别名: 1-[4-(2-N-aziridylethoxy)phenyl]-1,2-diphenyl-2-iodoethylene；1-{2-[4-(2-Iodo-1,2-diphenylethenyl)phenoxy]ethyl}aziridine；1-[2-[4-(2-iodo-1,2-diphenylethenyl)phenoxy]ethyl]aziridine
• CAS: 113202-47-4
• 化学式: C₂₄H₂₂INO
• 分子量: 467.349
• InChiKey: YBRBURCLTCCSKW-UHFFFAOYSA-N

物化性质

• 沸点：
  531.3±50.0 °C(Predicted)
• 密度：
  1.450±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  12.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-[4-(2-N-aziridylethoxy)phenyl]-1,2-diphenyl-2-trimethylstannylethylene 在 碘 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到1-<4-(2-N-aziridylethoxy)phenyl>-1,2-diphenyl-2-iodoethylene
  参考文献：
  名称：

  [125I]Iododesethyl tamoxifen aziridine: Synthesis and covalent labeling of the estrogen receptor with an iodine-labeled affinity label

  摘要：

  Iododesethyl tamoxifen aziridine (I-Tam-Az), an analog of the estrogen receptor-affinity label tamoxifen aziridine (Tam-Az) in which the ethyl group has been replaced by an iodine, has been prepared by two routes: (a) metallation of a bromotriarylethylene system, followed by reaction with iodine, and aziridinylation, and (b) direct iodination of a trimethylstannyl triarylethylene system that is the immediate precursor of I-Tam-Az. The latter method can be used to prepare [125I]I-Tam-Az rapidly and in good yield, both at carrier-added and no-carrier-added levels; specific activities greater than 200 Ci/mmol have been obtained. In competitive radiometric binding assays with the estrogen receptor, I-Tam-Az has an apparent affinity of ca. 20%, equivalent to that of Tam-Az. It also undergoes rapid and selective time-dependent, irreversible binding to the estrogen receptor. [125I]I-Tam-Az reacts covalently with estrogen receptor in uterine cytosol preparations; its attachment is rapid and efficient, but somewhat less selective than that of Tam-Az. Estrogen receptor in intact MCF-7 human breast cancer cells can also be labeled with [125I]I-Tam-Az, and autoradiographic analysis of salt extracts of labeled nuclear estrogen receptor on SDS-polyacrylamide slab gels shows highly selective labeling of a 65K protein. [125I]I-Tam-Az is an efficient, selective affinity label for the estrogen receptor, available at high specific activity, and should be useful in studies on estrogen receptor structure, dynamics, and chromatin interactions.

  DOI：

  10.1016/0039-128x(86)90017-6

文献信息

• [125I]Iododesethyl tamoxifen aziridine: Synthesis and covalent labeling of the estrogen receptor with an iodine-labeled affinity label
  作者：Francesco G. Salituro、Kathryn E. Carlson、Jonathan F. Elliston、Benita S. Katzenellenbogen、John A. Katzenellenbogen

  DOI：10.1016/0039-128x(86)90017-6

  日期：1986.11

  Iododesethyl tamoxifen aziridine (I-Tam-Az), an analog of the estrogen receptor-affinity label tamoxifen aziridine (Tam-Az) in which the ethyl group has been replaced by an iodine, has been prepared by two routes: (a) metallation of a bromotriarylethylene system, followed by reaction with iodine, and aziridinylation, and (b) direct iodination of a trimethylstannyl triarylethylene system that is the immediate precursor of I-Tam-Az. The latter method can be used to prepare [125I]I-Tam-Az rapidly and in good yield, both at carrier-added and no-carrier-added levels; specific activities greater than 200 Ci/mmol have been obtained. In competitive radiometric binding assays with the estrogen receptor, I-Tam-Az has an apparent affinity of ca. 20%, equivalent to that of Tam-Az. It also undergoes rapid and selective time-dependent, irreversible binding to the estrogen receptor. [125I]I-Tam-Az reacts covalently with estrogen receptor in uterine cytosol preparations; its attachment is rapid and efficient, but somewhat less selective than that of Tam-Az. Estrogen receptor in intact MCF-7 human breast cancer cells can also be labeled with [125I]I-Tam-Az, and autoradiographic analysis of salt extracts of labeled nuclear estrogen receptor on SDS-polyacrylamide slab gels shows highly selective labeling of a 65K protein. [125I]I-Tam-Az is an efficient, selective affinity label for the estrogen receptor, available at high specific activity, and should be useful in studies on estrogen receptor structure, dynamics, and chromatin interactions.