(+/-)-OO'-dibenzylcoclaurine | 47765-29-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (+/-)-OO'-dibenzylcoclaurine
• 英文别名: 7-benzyloxy-1-(4-benzyloxy-benzyl)-6-methoxy-1,2,3,4-tetrahydro-isoquinoline；7-Benzyloxy-1-(4-benzyloxy-benzyl)-6-methoxy-1,2,3,4-tetrahydro-isochinolin；7,12-O,O'-dibenzylcoclaurine；6-methoxy-7-phenylmethoxy-1-[(4-phenylmethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline
• CAS: 47765-29-7
• 化学式: C₃₁H₃₁NO₃
• 分子量: 465.592
• InChiKey: XJDFIDRLFSFTJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-OO'-dibenzylcoclaurine 在 四氯化锡 作用下， 以36%的产率得到1-(4-Benzyloxybenzyl)-1,2,3,4-tetrahydro-7-hydroxy-6-methoxy-isochinolin
  参考文献：
  名称：

  Simplified Tetrandrine Congeners as Possible Antihypertensive Agents with a Dual Mechanism of Action

  摘要：

  A series of O- and/or N-substituted derivatives of (+/-)-coclaurine (1a) were synthesized as simplified structural mimics of the antihypertensive alkaloid tetrandrine (2) and assayed for binding to brain cortical sites labeled with the alpha(1)-adrenergic radioligand [H-3]prazosin or the calcium channel radioligand [H-3]-diltiazem. The introduction of O-benzyl groups on the coclaurine molecule, which exhibits only adrenergic antagonist activity, led to the appearance of calcium channel blocking activity comparable to that of tetrandrine while retaining adrenolytic activity in the same concentration range. Contraction of aortal rings with noradrenaline or KCl was relaxed more potently by some of these coclaurine derivatives than by tetrandrine, suggesting leads for the development of novel antihypertensive drugs with a dual mechanism of action.

  DOI：

  10.1021/np030022+
• 作为产物：
  描述：

  3,4-二氢-6-甲氧基-7-(苯基甲氧基)-1-[[4-(苯基甲氧基)苯基]甲基]-异喹啉 在 sodium tetrahydroborate 作用下， 以68%的产率得到(+/-)-OO'-dibenzylcoclaurine
  参考文献：
  名称：

  Simplified Tetrandrine Congeners as Possible Antihypertensive Agents with a Dual Mechanism of Action

  摘要：

  A series of O- and/or N-substituted derivatives of (+/-)-coclaurine (1a) were synthesized as simplified structural mimics of the antihypertensive alkaloid tetrandrine (2) and assayed for binding to brain cortical sites labeled with the alpha(1)-adrenergic radioligand [H-3]prazosin or the calcium channel radioligand [H-3]-diltiazem. The introduction of O-benzyl groups on the coclaurine molecule, which exhibits only adrenergic antagonist activity, led to the appearance of calcium channel blocking activity comparable to that of tetrandrine while retaining adrenolytic activity in the same concentration range. Contraction of aortal rings with noradrenaline or KCl was relaxed more potently by some of these coclaurine derivatives than by tetrandrine, suggesting leads for the development of novel antihypertensive drugs with a dual mechanism of action.

  DOI：

  10.1021/np030022+

文献信息

• Absolute configuration and biosynthesis of tiliacorine and tiliacorinine
  作者：Dewan S. Bhakuni、Sudha Jain

  DOI：10.1039/p19810002598

  日期：——

  the biotransformation into tiliacorine and tilacorinine. Experiments with (±)-N-[14C]methyl[1-3H]coclaurine demonstrated that the hydrogen atom at the asymmetric centre in the 1-benzyltetrahydroisoquinoline precursor is retained in the bioconversion into tiliacorine and tiliacorinine. Biosynthetic experiments with (R)- and (S)-N-methylcoclaurines established that tiliacorine has the S- and R-configuration

  将（±）-coclaurine，（±）-norcoclaurine，（±）-N-甲基coclaurine和二脱氢-N-甲基coclaurinium碘化物掺入race树皮中的t草碱和t草碱中。已经研究了（±）-N-甲基coclaurine的具体用途。证据表明，这两个碱基的“一半”均来自N-甲基钴尿素。双标记实验用（±） - ñ -甲基[1- 3 H，6- ö甲基14 C] coclaurine表明，ø从之一甲基功能Ñ-甲基可乐碱单位在生物转化为t草碱和tilacorinine中丢失。-与（±）实验ñ - [ 14 C]甲基[1- 3 H] coclaurine表明，在1-benzyltetrahydroisoquinoline前体的不对称中心的氢原子被保留在生物转化成tiliacorine和tiliacorinine。（R）-和（S）-N-甲基coclaurines的生物合成实验表明，t草碱
• Identification and characterization of human neuronal voltage-gated calcium channel gamma 3 subunit gene
  作者：Jiahui Xia、Huali Zhang、Dongsheng Tang、Xixiang Tang、Heping Dai、Qian Pan、Zhigao Long、Xiaodong Liao

  DOI：10.1007/bf02886324

  日期：2000.12

  By homologous expressed sequence tag (EST) searching, one EST (GenBank: W29095) was obtained, which shows 75% identity in 435 bp overlap with the coding sequence of mouse Cacng2 gene. A 1 545 bp cDNA fragment was obtained from the nested polymerase chain reaction (PCR) and rapid applification of cDNA end (RACE) reaction in the human brain prefrontal cortex cDNA library and the human brain Ready cDNA with the primers designed on W29095. The fragment contained a 948-bp open reading frame (ORF) encoding 315 amino acids, and was named CACNG3. As it was identical to a BAC clone (GenBank: AC004125) from chromosome 16p12-p13.1, the CACNG3 gene was mapped to human chromosome 16p12-p13.1, and the coding region was composed of 4 exons. Reverse transcription PCR (RT-PCR) analysis showed that the CACNG3 gene expressed in human adult brain and fetal brain. Single strand comformation polymorphism (SSCP) analysis was performed in 3 pedigrees with autosomal recessive retinitis pigmentosa, 8 pedigrees with autosomal recessive retinitis pigmentosa accompanied by deafness and 2 pedigrees with epilepsy, but no mutation was detected.
• Yamaguchi; Nakano, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1959, vol. 79, p. 1106
  作者：Yamaguchi、Nakano

  DOI：——

  日期：——
• Simplified Tetrandrine Congeners as Possible Antihypertensive Agents with a Dual Mechanism of Action
  作者：Patricio Iturriaga-Vásquez、Raquel Miquel、M. Dolores Ivorra、M. Pilar D'Ocon、Bruce K. Cassels

  DOI：10.1021/np030022+

  日期：2003.7.1

  A series of O- and/or N-substituted derivatives of (+/-)-coclaurine (1a) were synthesized as simplified structural mimics of the antihypertensive alkaloid tetrandrine (2) and assayed for binding to brain cortical sites labeled with the alpha(1)-adrenergic radioligand [H-3]prazosin or the calcium channel radioligand [H-3]-diltiazem. The introduction of O-benzyl groups on the coclaurine molecule, which exhibits only adrenergic antagonist activity, led to the appearance of calcium channel blocking activity comparable to that of tetrandrine while retaining adrenolytic activity in the same concentration range. Contraction of aortal rings with noradrenaline or KCl was relaxed more potently by some of these coclaurine derivatives than by tetrandrine, suggesting leads for the development of novel antihypertensive drugs with a dual mechanism of action.