1,4-bis-[(N,N'-bis-tert-butyloxycarbonyl)guanidinomethyl]-2-iodobenzene | 687635-87-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,4-bis-[(N,N'-bis-tert-butyloxycarbonyl)guanidinomethyl]-2-iodobenzene
• CAS: 687635-87-6
• 化学式: C₃₀H₄₇IN₆O₈
• 分子量: 746.643
• InChiKey: RKCPRZJKDYYENN-UHFFFAOYSA-N

物化性质

• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  45.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  188.44
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1,4-bis-[(N,N'-bis-tert-butyloxycarbonyl)guanidinomethyl]-2-iodobenzene 在 三异丙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-[[4-[(diaminomethylideneamino)methyl]-2-iodophenyl]methyl]guanidine
  参考文献：
  名称：

  Meta-iodobenzylguanidine derivatives containing a second guanidine moiety

  摘要：

  Radioiodinated meta-iodobenzylguanidine (MIBG) is used in the diagnosis and therapy of various neuroendocrine tumors. To investigate whether an additional guanidine function in the structure of MIBG will yield analogues that may potentially enhance tumor-to-target ratios, two derivatives-one with a guanidine moiety and another with a guanidinomethyl group at the 4-position of MIBG-were prepared. In the absence of any uptake-1 inhibiting conditions, the uptake of 4-guanidinomethyl-3-[(131) I]iodobenzylguanidine ([I-131]GMIBG) by SK-N-SH cells in vitro was 1.7+/-0.1% of input counts, compared to a value of 40.3+/-1.4% for [I-125]MIBG suggesting that guanidinomethyl group at the 4-position negated the biological properties of MIBG. On the other hand, 4-guanidino-3-[I-131]iodobenzylguanidine ([I-131]GIBG) had an uptake (5.6+/-0.3%) that was 12-13% that of [I-125]MIBG (46.1+/-2.7%), and the ratio of uptake by control over DMI-treated (nonspecific) cultures was higher for [I-131]GIBG (20.9+/-0.3) than [I-125]MIBG itself (15.0+/-2.7). The exocytosis of [I-131]GIBG and [I-125]MIBG from SK-N-SH cells was similar. The uptake of [I-131]GIBG in the mouse target tissues, heart and adrenals, as well as in a number of other tissues was about half that of [I-121]MIBG. These results suggest that substitution of guanidine functions, especially a guanidinomethyl group, in MIBG structure may not be advantageous. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.026
• 作为产物：
  描述：

  1,4-二甲基-2-碘苯 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 、 1,1'-偶氮(氰基环己烷) 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 1,4-bis-[(N,N'-bis-tert-butyloxycarbonyl)guanidinomethyl]-2-iodobenzene
  参考文献：
  名称：

  Meta-iodobenzylguanidine derivatives containing a second guanidine moiety

  摘要：

  Radioiodinated meta-iodobenzylguanidine (MIBG) is used in the diagnosis and therapy of various neuroendocrine tumors. To investigate whether an additional guanidine function in the structure of MIBG will yield analogues that may potentially enhance tumor-to-target ratios, two derivatives-one with a guanidine moiety and another with a guanidinomethyl group at the 4-position of MIBG-were prepared. In the absence of any uptake-1 inhibiting conditions, the uptake of 4-guanidinomethyl-3-[(131) I]iodobenzylguanidine ([I-131]GMIBG) by SK-N-SH cells in vitro was 1.7+/-0.1% of input counts, compared to a value of 40.3+/-1.4% for [I-125]MIBG suggesting that guanidinomethyl group at the 4-position negated the biological properties of MIBG. On the other hand, 4-guanidino-3-[I-131]iodobenzylguanidine ([I-131]GIBG) had an uptake (5.6+/-0.3%) that was 12-13% that of [I-125]MIBG (46.1+/-2.7%), and the ratio of uptake by control over DMI-treated (nonspecific) cultures was higher for [I-131]GIBG (20.9+/-0.3) than [I-125]MIBG itself (15.0+/-2.7). The exocytosis of [I-131]GIBG and [I-125]MIBG from SK-N-SH cells was similar. The uptake of [I-131]GIBG in the mouse target tissues, heart and adrenals, as well as in a number of other tissues was about half that of [I-121]MIBG. These results suggest that substitution of guanidine functions, especially a guanidinomethyl group, in MIBG structure may not be advantageous. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.026