N-(2,2-二甲氧基乙基)-1-(3-甲氧基苯基)甲亚胺 | 39964-84-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: N-(2,2-二甲氧基乙基)-1-(3-甲氧基苯基)甲亚胺
• 英文名称: (3-Methoxy-benzylidenamino)-acetaldehyd-dimethylacetal
• 英文别名: N-(2,2-dimethoxyethyl)-1-(3-methoxyphenyl)methanimine
• CAS: 39964-84-6
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: ISDDMVDVRURZNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  40
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2,2-二甲氧基乙基)-1-(3-甲氧基苯基)甲亚胺 在 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 生成 ethyl (1,2-bis(3-methoxyphenyl)ethyl)(2,2-dimethoxyethyl)carbamate
  参考文献：
  名称：

  Discovery of 1-arylcarbonyl-6,7-dimethoxyisoquinoline derivatives as glutamine fructose-6-phosphate amidotransferase (GFAT) inhibitors

  摘要：

  Through high throughput screening and subsequent hit identification and optimization, we synthesized a series of 1-arylcarbonyl-6,7-dimethoxyisoquinoline derivatives as the first reported potent and reversible GFAT inhibitors. SAR studies of this class of compounds indicated significant impact on GFAT inhibition potency by substitutions on the A-ring and C-ring. The ketone group was found to be necessary for high potency. Compound 28 (RO0509347) demonstrated potent GFAT inhibition (IC(50) = 1 mu M) with a desirable pharmacokinetic profile in rats, and showed significant efficacy in reducing the glucose excursion in an OGTT test in ob/ob mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.009
• 作为产物：
  描述：

  3-甲氧基苯甲醛 、 氨基乙醛缩二甲醇 以 甲苯 为溶剂， 生成 N-(2,2-二甲氧基乙基)-1-(3-甲氧基苯基)甲亚胺
  参考文献：
  名称：

  基于黄嘌呤的强效和选择性磷酸二酯酶抑制剂5

  摘要：

  PDE5抑制剂是治疗勃起功能障碍的有用治疗剂。已鉴定出一系列新的黄嘌呤衍生物作为PDE5的有效抑制剂，对其他PDE异构体（包括PDE6）具有良好的选择性。在狗中进行的研究表明，化合物21具有出色的口服生物利用度。

  DOI：

  10.1016/j.bmcl.2006.11.019

文献信息

• Potent and selective xanthine-based inhibitors of phosphodiesterase 5
  作者：Nichola J. Arnold、Ruth Arnold、David Beer、Gurdip Bhalay、Stephen P. Collingwood、Sarah Craig、Nicholas Devereux、Mark Dodds、Andrew R. Dunstan、Robin A. Fairhurst、David Farr、Joseph D. Fullerton、Angela Glen、Sylvie Gomez、Sandra Haberthuer、Julia D.I. Hatto、Colin Howes、Darryl Jones、Thomas H. Keller、Beate Leuenberger、Heinz E. Moser、Irene Muller、Reto Naef、Paul A. Nicklin、David A. Sandham、Katharine L. Turner、Morris F. Tweed、Simon J. Watson、Mauro Zurini

  DOI：10.1016/j.bmcl.2006.11.019

  日期：2007.4

  Inhibitors of PDE5 are useful therapeutic agents for treatment of erectile dysfunction. A series of novel xanthine derivatives has been identified as potent inhibitors of PDE5, with good levels of selectivity against other PDE isoforms, including PDE6. Studies in the dog indicate excellent oral bioavailability for compound 21.

  PDE5抑制剂是治疗勃起功能障碍的有用治疗剂。已鉴定出一系列新的黄嘌呤衍生物作为PDE5的有效抑制剂，对其他PDE异构体（包括PDE6）具有良好的选择性。在狗中进行的研究表明，化合物21具有出色的口服生物利用度。
• Inhibiting phenylethanolamine N-methyltransferase with thiadiazolo and
  申请人：SmithKline Corporation

  公开号：US04258049A1

  公开（公告）日：1981-03-24

  Thiadiazolo- and oxadiazolotetrahydroisoquinoline compounds are inhibitors of phenylethanolamine N-methyltransferase.

  Thiadiazolo-和oxadiazolotetrahydroisoquinoline化合物是苯乙醇胺N-甲基转移酶的抑制剂。
• Method of producing alpha.sub.2 antagonism
  申请人：Smithkline Corporation

  公开号：US04352809A1

  公开（公告）日：1982-10-05

  Method of producing alpha.sub.2 antagonism by administering thiadiazolo- and oxadiazolotetrahydroisoquinoline compounds.

  通过给予噻二唑和氧二唑四氢异喹啉化合物，制造α.sub.2拮抗的方法。
• Multisubstrate inhibitors of dopamine .beta.-hydroxylase. 2. Structure-activity relationships at the phenethylamine binding site
  作者：Lawrence I. Kruse、Carl Kaiser、Walter E. DeWolf、James S. Frazee、Stephen T. Ross、Joyce Wawro、Merrie Wise、Kathryn E. Flaim、John L. Sawyer

  DOI：10.1021/jm00386a008

  日期：1987.3

  1-Aralkylimidazole-2-thiones have been shown to be potent multisubstrate inhibitors of dopamine beta-hydroxylase (DBH; EC 1.14.17.1). In the present study, a series of 1-benzylimidazole-2-thiones was prepared to explore the effects of substitution in the benzyl ring on the inhibition of DBH. A detailed structure-activity relationship for in vitro activity was discovered and this was shown by a modified Hansch analysis to correlate (r = 0.91) with four key structural features of the benzyl ring: the presence of a hydroxyl at the 4-position, molar refractivity at the 3-, 4-, and 5-positions, inductive effects of the substituents at the 3-, 4-, and 5-positions, and pi-electron density. The affinity (Kis) of eight substituted inhibitors for DBH was shown to correlate (r = 0.75) with the affinity (KD) of comparably substituted tyramines for the ternary DBH-oxygen-tyramine complex. This correlate is used to support the hypothesis that binding of inhibitor to DBH occurs in a fashion that mimics the binding of tyramine substrates. The most potent inhibitors were selected for study in vivo in the spontaneously hypertensive rat model of hypertension. The changes in vascular dopamine and norepinephrine levels that resulted from oral administration of the inhibitors corresponded to the observed reduction in mean arterial blood pressure. A divergence between in vitro potency and in vivo efficacy upon oral dosing was noted and is suggested to result from an in vivo metabolic conjugation of the phenolic group of inhibitor.
• Euerby, Melvin R.; Waigh, Roger D., Journal of Chemical Research, Miniprint, 1987, # 2, p. 501 - 526
  作者：Euerby, Melvin R.、Waigh, Roger D.

  DOI：——

  日期：——