5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinoline (nortehuanine) | 1745-06-8

• 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: 5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinoline (nortehuanine)
• 英文别名: 5,6,7-trimethoxy-1,2,3,4-tetrahydro-isoquinoline；1,2,3,4-tetrahydro-5,6,7-trimethoxyisoquinoline；5,6,7-trimethoxytetrahydroisoquinoline；nortehuanine；5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinoline；6,7,8-Trimethoxy-1,2,3,4-tetrahydro-isochinolin
• CAS: 1745-06-8
• 化学式: C₁₂H₁₇NO₃
• mdl: MFCD00835601
• 分子量: 223.272
• InChiKey: HMJWNMXNHQIAGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinoline (nortehuanine) 在 盐酸 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 5,6,7-Trimethoxy-3,4-dihydroisoquinoline;hydrochloride
  参考文献：
  名称：

  The Reaction of 3,4-Dihydroisoquinolines With Malonic Acid and Its Derivatives

  摘要：

  各种 3,4-二氢异喹啉与丙二酸反应可以得到相应的 1,2,3,4-四氢-1-异喹啉乙酸，收率很高，而与氰基乙酸和丙二酸半乙酯反应则可以分别得到 1,2,3,4-四氢-1-异喹啉乙腈和 1,2,3,4-四氢-1-异喹啉乙酸酯。在此反应中使用其他不能脱羧的 1,3-二羰基，可得到正常的加成产物。

  DOI：

  10.1055/s-1987-33431
• 作为产物：
  描述：

  2-(2,3,4-三甲氧基苯基)乙胺 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 26.17h， 生成 5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinoline (nortehuanine)
  参考文献：
  名称：

  SAR Based Design of Nicotinamides as a Novel Class of Androgen Receptor Antagonists for Prostate Cancer

  摘要：

  Molecular knowledge of pure antagonism and systematic SAR study offered a direction for structural optimization of DIMN to provide nicotinamides as a novel series of AR antagonists. Nicotinamides with extended linear scaffold bearing sterically bulky alkoxy groups on isoquinoline end were synthesized for H12 displacement AR binding affinity and molecular basis of antiandrogenic effect establish the optimized derivatives, 7au and 7bb, as promising candidates of second generation AR antagonists for advanced prostate cancer.

  DOI：

  10.1021/jm3014103

文献信息

• Approaches to Short-Acting Neuromuscular Blocking Agents:  Nonsymmetrical Bis-tetrahydroisoquinolinium Mono- and Diesters
  作者：Nirmal C. Dhar、Robert B. Maehr、Luke A. Masterson、John M. Midgley、John B. Stenlake、William B. Wastila

  DOI：10.1021/jm950477z

  日期：1996.1.1

  moiety have been studied as a means of promoting short action with high-potency neuromuscular block. Atracurium-related nonsymmetrical diesters showed high potency, freedom from vagal blockade at neuromuscular blocking doses, and short action. Nonsymmetrical monoesters were short acting but showed varying degrees of vagal block.

  非对称双季二酯和二酯结合了（1R）-laudanosinium基团的效力增强特性与第二个不受阻碍的季铵部分相结合，已被研究为通过高效力神经肌肉阻滞促进短效行动的手段。与阿曲库铵相关的非对称二酯显示出高效力，在神经肌肉阻滞剂量下不受迷走神经阻滞的作用，且作用时间短。非对称单酯是短效的，但表现出不同程度的迷走神经阻滞。
• 2 (OR 4) Amino 4 (or 2) N-hetero quinazolines
  申请人：Pfizer Inc.

  公开号：US03960861A1

  公开（公告）日：1976-06-01

  A series of novel 2-amino and 4-aminoquinazoline derivatives have been prepared, including their acid addition salts. These derivatives all possess a single nitrogen-containing benzo-fused heterocyclic ring moiety at either the 4- or 2- positions of the molecule, respectively, with the ring moiety being attached through the nitrogen atom to the aforesaid quinazoline nucleus. Such compounds are useful in therapy as highly potent antihypertensive agents. Methods for their preparation are described in detail, including various synthetic routes leading to the required novel intermediates.

  已制备一系列新颖的2-氨基和4-氨基喹唑啉衍生物，包括它们的酸加成盐。这些衍生物都在分子的4-或2-位置具有一个含氮苯融合杂环环基，该环基通过氮原子连接到上述喹唑啉核。这些化合物在治疗中具有高效的降压剂作用。详细描述了它们的制备方法，包括通往所需新颖中间体的各种合成途径。
• Studies on tetrahydroisoquinolines. XXVI. A biomimetic synthesis of 5-oxygenated 1,2,3,4-tetrahydroisoquinolines.
  作者：HIROSHI HARA、AKIRA TSUNASHIMA、HIROSHI SHINOKI、TOSHIFUMI AKIBA、OSAMU HOSHINO、BUNSUKE UMEZAWA

  DOI：10.1248/cpb.34.66

  日期：——

  Treatment with acetic anhydride-conc. sulufuric acid of o-quinol acetates (7, 11, 18, 19, 20, 28 and 34), which were derived from the corresponding 6-hydroxy-7-methoxytetrahydroisoquinolines (6, 12, 15, 16, 17, 27 and 31), gave the 5, 6-diacetates (8, 13, 21, 22, 23, 29 and 33, respectively). The diacetates were transformed into the corresponding 5, 6, 7-trimethoxytetrahydroisoquinolines (10, 14, 24, 25, 26, 30 and 32) by hydrolysis and subsequent methylation.

  用乙酸酐-缩合舒氟酸处理由相应的 6-羟基-7-甲氧基四氢异喹啉（6、12、15、16、17、27 和 31）衍生的邻喹啉乙酸酯（7、11、18、19、20、28 和 34），可得到 5、6-二乙酸酯（分别为 8、13、21、22、23、29 和 33）。通过水解和随后的甲基化，这些二乙酸酯被转化为相应的 5、6、7-三甲氧基四氢异喹啉（10、14、24、25、26、30 和 32）。
• Aminoquinazoline therapeutic agents
  申请人：Pfizer Inc.

  公开号：US04044136A1

  公开（公告）日：1977-08-23

  A series of novel 2-amino and 4-aminoquinazoline derivatives have been prepared, including their acid addition salts. These derivatives all possess a single nitrogen-containing benzo-fused heterocyclic ring moiety at either the 4- or 2-positions of the molecule, respectively, with the ring moiety being attached through the nitrogen atom to the aforesaid quinazoline nucleus. Such compounds are useful in therapy as highly potent antihypertensive agents. Methods for their preparation are described in detail, including various synthetic routes leading to the required novel intermediates.

  一系列新型的2-氨基和4-氨基喹唑啉衍生物已经制备出来，包括它们的酸加成盐。这些衍生物在分子的4-或2-位置上都具有单一的含氮苯并杂环环基，该环基通过氮原子与上述喹唑啉核结构连接。这些化合物作为高效的降压剂在治疗中有用。详细描述了它们的制备方法，包括导致所需新型中间体的各种合成途径。
• A Synthesis of Some Trimethoxylated 1,2,3,4-Tetrahydroisoquinoline Alkaloids via Pummerer Reaction of N-Trimethoxybenzyl-N-[2-(phenyl- sulfinyl)ethyl]formamides
  作者：Takehiro Sano、Tatsumi Shinohara、Akira Takeda、Jun Toda、Michiyo Kohno

  DOI：10.3987/com-98-8372

  日期：——