1-(benzo[a]heptalen-9[5H]-one-6,7-dihydro-1,2,3,10-tetramethoxy-7-carbamoyl)methyl-4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane | 1312808-72-2

• 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: 1-(benzo[a]heptalen-9[5H]-one-6,7-dihydro-1,2,3,10-tetramethoxy-7-carbamoyl)methyl-4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane
• 英文别名: 2-[4,7-bis(carboxymethyl)-10-[2-oxo-2-[[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]amino]ethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetic acid
• CAS: 1312808-72-2
• 化学式: C₃₆H₄₉N₅O₁₂
• 分子量: 743.811
• InChiKey: UNLZLSUQWXJCQM-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.1
• 重原子数：
  53
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  208
• 氢给体数：
  4
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  tri-tert-butyl 2,2’,2’’-(10-(2-methoxy-2-oxoethyl)-1,4,7,10-tetraazacy-cyclododecane-1,4,7-triyl)triacetate 在 N-甲基吗啉 、 水 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三氟乙酸 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 1-(benzo[a]heptalen-9[5H]-one-6,7-dihydro-1,2,3,10-tetramethoxy-7-carbamoyl)methyl-4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane
  参考文献：
  名称：

  Synthesis and characterisation of a novel tubulin-directed DO3A–colchicine conjugate with potential theranostic features

  摘要：

  Colchicine is a known tubulin binding agent enabling necrosis in tumors. A novel tubulin-directed DO3A-colchicine conjugate and its Gd(III) complex were prepared from N-deacetylcolchicine, coupling alkaloid and polyaza-alicyclic functions via a peptide coupling methodology. The longitudinal proton relaxivity of the Gd( III) complex in water at 4.7 T is 2.86 mM(-1) s(-1) and a similar efficacy as colchicine towards ovarian carcinoma cells in vitro. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.014

文献信息

• Synthesis and characterisation of a novel tubulin-directed DO3A–colchicine conjugate with potential theranostic features
  作者：Nicholas. J. Wardle、Tammy Kalber、Jimmy D. Bell、S.W. Annie Bligh

  DOI：10.1016/j.bmcl.2011.04.014

  日期：2011.6

  Colchicine is a known tubulin binding agent enabling necrosis in tumors. A novel tubulin-directed DO3A-colchicine conjugate and its Gd(III) complex were prepared from N-deacetylcolchicine, coupling alkaloid and polyaza-alicyclic functions via a peptide coupling methodology. The longitudinal proton relaxivity of the Gd( III) complex in water at 4.7 T is 2.86 mM(-1) s(-1) and a similar efficacy as colchicine towards ovarian carcinoma cells in vitro. (C) 2011 Elsevier Ltd. All rights reserved.