3-[4-[4-(2-Tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)piperidin-1-yl]pyridin-3-yl]-2-propenoic acid ethyl ester | 854261-73-7

• 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: 3-[4-[4-(2-Tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)piperidin-1-yl]pyridin-3-yl]-2-propenoic acid ethyl ester
• 英文别名: tert-butyl 7-[[1-[3-(3-ethoxy-3-oxoprop-1-enyl)pyridin-4-yl]piperidin-4-yl]methoxy]-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 854261-73-7
• 化学式: C₃₀H₃₉N₃O₅
• 分子量: 521.657
• InChiKey: MOTQJTVEZCBEIX-UHFFFAOYSA-N

物化性质

• 沸点：
  666.4±55.0 °C(predicted)
• 密度：
  1.167±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  81.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-[4-[4-(2-Tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)piperidin-1-yl]pyridin-3-yl]-2-propenoic acid ethyl ester 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 ethyl 3-[4-[4-(2-amidino-1,2,3,4-tetrahydroisoquinolin-7-ylmethoxy)piperidin-1-yl]piperidin-3-yl]-2-propionate
  参考文献：
  名称：

  Discovery of novel tetrahydroisoquinoline derivatives as potent and selective factor Xa inhibitors

  摘要：

  A series of novel 2,7-disubstituted tetrahydroisoquinoline derivatives were designed and synthesized. Among these derivatives, compounds I and 2 (JTV-803) exhibited potent inhibitory activity against FXa and good selectivity with respect to other serine proteases (thrombin, plasmin, and trypsin). In addition, compound 2 exhibited potent anti-FXa activity after intravenous and oral administration to cynomolgus monkey, and showed a dose-dependent antithrombotic effect in a rat model of venous thrombosis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.033
• 作为产物：
  描述：

  7-甲氧基异喹啉 在 platinum(IV) oxide 、 palladium on activated charcoal sodium hydroxide 、 氢溴酸 、 氢气 、 sodium hydride 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、303.98 kPa 条件下， 生成 3-[4-[4-(2-Tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)piperidin-1-yl]pyridin-3-yl]-2-propenoic acid ethyl ester
  参考文献：
  名称：

  Discovery of novel tetrahydroisoquinoline derivatives as potent and selective factor Xa inhibitors

  摘要：

  A series of novel 2,7-disubstituted tetrahydroisoquinoline derivatives were designed and synthesized. Among these derivatives, compounds I and 2 (JTV-803) exhibited potent inhibitory activity against FXa and good selectivity with respect to other serine proteases (thrombin, plasmin, and trypsin). In addition, compound 2 exhibited potent anti-FXa activity after intravenous and oral administration to cynomolgus monkey, and showed a dose-dependent antithrombotic effect in a rat model of venous thrombosis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.033

文献信息

• Amidine compounds
  申请人：JAPAN TOBACCO INC.

  公开号：US20040006099A1

  公开（公告）日：2004-01-08

  A compound of the formula [I] 1 wherein R 1 , R 2 and R 3 are the same or different and each is hydrogen atom, hydroxy, lower alkyl or aryl, R is a group of the formula 2 wherein each symbol is as defined in the specification, a salt thereof or a prodrug thereof. The compound of the present invention, a salt thereof and a prodrug thereof are useful as factor Xa inhibitor and blood coagulation inhibitor, and are useful for the prophylaxis and/or treatment of diseases caused by blood coagulation or thrombus.

  化合物的式子为[I]1，其中R1、R2和R3相同或不同，且每个都是氢原子、羟基、低碳基或芳基，R是式子2的基团，其中每个符号如规范中定义的那样，其盐或前药。本发明的化合物、其盐和前药可用作因子Xa抑制剂和血液凝固抑制剂，并可用于预防和/或治疗由血液凝固或血栓引起的疾病。
• Discovery of novel tetrahydroisoquinoline derivatives as potent and selective factor Xa inhibitors
  作者：Hiroshi Ueno、Katsuyuki Yokota、Jun-ichi Hoshi、Katsutaka Yasue、Mikio Hayashi、Itsuo Uchida、Kazuo Aisaka、Yasunori Hase、Susumu Katoh、Hidetsura Cho

  DOI：10.1016/j.bmcl.2004.10.033

  日期：2005.1

  A series of novel 2,7-disubstituted tetrahydroisoquinoline derivatives were designed and synthesized. Among these derivatives, compounds I and 2 (JTV-803) exhibited potent inhibitory activity against FXa and good selectivity with respect to other serine proteases (thrombin, plasmin, and trypsin). In addition, compound 2 exhibited potent anti-FXa activity after intravenous and oral administration to cynomolgus monkey, and showed a dose-dependent antithrombotic effect in a rat model of venous thrombosis. (C) 2004 Elsevier Ltd. All rights reserved.