(S)‐6,7‐dimethoxy‐3‐hydroxymethyl‐1,2,3,4‐tetrahydroisoquinoline | 175550-99-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (S)‐6,7‐dimethoxy‐3‐hydroxymethyl‐1,2,3,4‐tetrahydroisoquinoline
• 英文别名: (S)-6,7-dimethoxy-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline；(S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquin-3-yl methanol；[(3S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-3-yl]methanol
• CAS: 175550-99-9
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: WFLGZUQISHZFPS-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)‐6,7‐dimethoxy‐3‐hydroxymethyl‐1,2,3,4‐tetrahydroisoquinoline 在 咪唑 、 氢氧化钾 、 N-氯代丁二酰亚胺 、 四丁基碘化铵 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成
  参考文献：
  名称：

  An efficient asymmetric synthesis of allo- and pseudo-7,8-dimethoxyberbane systems through tin-mediated three component coupling

  摘要：

  Three component coupling reactions of chiral 3-substituted 6,7-dimethoxy-3,4-dihydroisoquinoline with allylic tin reagents and unsaturated acid chlorides followed by intramolecular Diels-Alder reactions afford allo- and pseudo-7,8-dimethoxyberbane systems in high diastereomeric excess.

  DOI：

  10.1016/0957-4166(96)00027-4
• 作为产物：
  描述：

  左旋多巴 在 lithium aluminium tetrahydride 、 硫酸 、 palladium 10% on activated carbon 、 氢气 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 、 丙酮 为溶剂， 反应 10.5h， 生成 (S)‐6,7‐dimethoxy‐3‐hydroxymethyl‐1,2,3,4‐tetrahydroisoquinoline
  参考文献：
  名称：

  Anticancer activity of ruthenium(II) arene complexes bearing 1,2,3,4-tetrahydroisoquinoline amino alcohol ligands

  摘要：

  Ruthenium complexes offer potential reduced toxicity compared to current platinum anticancer drugs. 1,2,3,4-tetrahydrisoquinoline amino alcohol ligands were synthesised, characterised and coordinated to an organometallic Ru(II) centre. These complexes were evaluated for activity against the cancer cell lines MCF-7, A549 and MDA-MB-231 as well as for toxicity in the normal cell line MDBK. They were observed to be moderately active against only the MCF-7 cells with the best IC50 value of 34 mu M for the cis-diastereomeric complex C4. They also displayed excellent selectivity by being relatively inactive against the normal MDBK cell line with SI values ranging from 2.3 to 7.4. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.048

文献信息

• Structure and Biocatalytic Scope of Coclaurine <i>N</i> ‐Methyltransferase
  作者：Matthew R. Bennett、Mark L. Thompson、Sarah A. Shepherd、Mark S. Dunstan、Abigail J. Herbert、Duncan R. M. Smith、Victoria A. Cronin、Binuraj R. K. Menon、Colin Levy、Jason Micklefield

  DOI：10.1002/anie.201805060

  日期：2018.8.13

  plant secondary metabolites, which have been exploited to develop analgesics, antibiotics, antitumor agents, and other therapeutic agents. Biosynthesis of BIAs proceeds via a common pathway from tyrosine to (S)‐reticulene at which point the pathway diverges. Coclaurine N‐methyltransferase (CNMT) is a key enzyme in the pathway to (S)‐reticulene, installing the N‐methyl substituent that is essential for

  苄基异喹啉生物碱 (BIA) 是结构多样的植物次生代谢物家族，已被用来开发镇痛药、抗生素、抗肿瘤剂和其他治疗剂。BIA 的生物合成通过从酪氨酸到 ( S )-网状荠烯的共同途径进行，此时该途径出现分歧。椰壳碱N-甲基转移酶 (CNMT) 是 ( S )-网状荠烯途径中的关键酶，安装N-甲基取代基，这对于许多 BIA 的生物活性至关重要。在本文中，我们描述了 CNMT 的第一个晶体结构，它与诱变研究一起定义了酶活性位点的结构。还利用一系列天然和合成底物以及辅因子类似物探索了 CNMT 的特异性。这项研究的知识可用于生成生产 BIA 或合成衍生物所需的改进 CNMT 变体。
• An organogel formed from a cyclic β-aminoalcohol
  作者：Chuanqing Kang、Zheng Bian、Yabing He、Fushe Han、Xuepeng Qiu、Lianxun Gao

  DOI：10.1039/c1cc13179f

  日期：——

  A new organogelator with unique structural feature of a cyclic β-aminoalcohol is presented as the first example of gelation by aminoalcohol through hydrogen-bonding between hydroxy and amine.

  作为氨基甲醇通过羟基和胺之间的氢键作用凝胶化的第一个实例，介绍了一种具有独特结构特征的新型环δ-氨基甲醇有机凝胶剂。
• An efficient asymmetric synthesis of allo- and pseudo-7,8-dimethoxyberbane systems through tin-mediated three component coupling
  作者：Yoshikazu Haraguchi、Sinpei Kozima、Ryohei Yamaguchi

  DOI：10.1016/0957-4166(96)00027-4

  日期：1996.2

  Three component coupling reactions of chiral 3-substituted 6,7-dimethoxy-3,4-dihydroisoquinoline with allylic tin reagents and unsaturated acid chlorides followed by intramolecular Diels-Alder reactions afford allo- and pseudo-7,8-dimethoxyberbane systems in high diastereomeric excess.
• Anticancer activity of ruthenium(II) arene complexes bearing 1,2,3,4-tetrahydroisoquinoline amino alcohol ligands
  作者：Madichaba P. Chelopo、Sachin A. Pawar、Mxolisi K. Sokhela、Thavendran Govender、Hendrik G. Kruger、Glenn E.M. Maguire

  DOI：10.1016/j.ejmech.2013.05.048

  日期：2013.8

  Ruthenium complexes offer potential reduced toxicity compared to current platinum anticancer drugs. 1,2,3,4-tetrahydrisoquinoline amino alcohol ligands were synthesised, characterised and coordinated to an organometallic Ru(II) centre. These complexes were evaluated for activity against the cancer cell lines MCF-7, A549 and MDA-MB-231 as well as for toxicity in the normal cell line MDBK. They were observed to be moderately active against only the MCF-7 cells with the best IC50 value of 34 mu M for the cis-diastereomeric complex C4. They also displayed excellent selectivity by being relatively inactive against the normal MDBK cell line with SI values ranging from 2.3 to 7.4. (C) 2013 Elsevier Masson SAS. All rights reserved.