methyl (2S,6S,12Z,13aS,14aR,16aS)-6-[(tert-butoxycarbonyl)amino]-2-hydroxy-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate | 300831-46-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S,6S,12Z,13aS,14aR,16aS)-6-[(tert-butoxycarbonyl)amino]-2-hydroxy-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate
• 英文别名: methyl (1S,4R,6S,7Z,14S,18S)-18-hydroxy-14-[(2-methylpropan-2-yl)oxycarbonylamino]-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylate
• CAS: 300831-46-3
• 化学式: C₂₄H₃₇N₃O₇
• 分子量: 479.574
• InChiKey: XDUPXKNQBXADLI-FLGZVWNZSA-N

物化性质

• 沸点：
  696.9±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2S,6S,12Z,13aS,14aR,16aS)-6-[(tert-butoxycarbonyl)amino]-2-hydroxy-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate 在 盐酸 、 偶氮二甲酸二异丙酯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (Z)-(1S,4R,6S,14S,18R)-14-Cyclopentyloxycarbonylamino-18-(7-methoxy-2-methoxycarbonyl-quinolin-4-yloxy)-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.0^4,6]nonadec-7-ene-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of BILN 2061, an HCV NS3 Protease Inhibitor with Proven Antiviral Effect in Humans

  摘要：

  The synthesis of BILN 2061, an NS3 protease inhibitor with proven antiviral effect in humans, was accomplished in a convergent manner from four building blocks. The procedure described here was suitable for the preparation of multigram quantities of BILN 2061 for preclinical pharmacological evaluation.

  DOI：

  10.1021/ol0489907
• 作为产物：
  描述：

  (1R,2S)-1-氨基-2-乙烯基环丙烷甲酸甲酯 在 RuCl₂[(PCy₃)(2-isopropoxybenzylidene)] 盐酸 、 lithium hydroxide 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 methyl (2S,6S,12Z,13aS,14aR,16aS)-6-[(tert-butoxycarbonyl)amino]-2-hydroxy-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate
  参考文献：
  名称：

  Synthesis of BILN 2061, an HCV NS3 Protease Inhibitor with Proven Antiviral Effect in Humans

  摘要：

  The synthesis of BILN 2061, an NS3 protease inhibitor with proven antiviral effect in humans, was accomplished in a convergent manner from four building blocks. The procedure described here was suitable for the preparation of multigram quantities of BILN 2061 for preclinical pharmacological evaluation.

  DOI：

  10.1021/ol0489907

文献信息

• Macrocyclic peptides active against the hepatitis C virus
  申请人：Boehringer Ingelheim (Canada) Ltd.

  公开号：US20030224977A1

  公开（公告）日：2003-12-04

  Compounds of formula I: 1 wherein R 1 is hydroxy or NHSO 2 R 1A wherein R 1A is (C 1-8 )alkyl, (C 3-7 )cycloalkyl or {(C 1-6 )alkyl-(C 3-7 )cycloalkyl}, which are all optionally substituted from 1 to 3 times with halo, cyano, nitro, O(C 1-6 )alkyl, amido, amino or phenyl, or R 1A is C 6 or C 10 aryl which is optionally substituted from 1 to 3 times with halo, cyano, nitro, (C 1-6 )alkyl, O(C 1-6 )alkyl, amido, amino or phenyl; R 2 is (C 5-6 )cycloalkyl and R 3 is cyclopentyl; or a pharmaceutically acceptable salt thereof, useful as inhibitors of the HCV NS3 protease.

  式I的化合物：其中R1是羟基或NHSO2R1A，其中R1A是（C1-8）烷基，（C3-7）环烷基或（C1-6）烷基-（C3-7）环烷基，这些都可以选择地被卤素，氰基，硝基，O（C1-6）烷基，酰胺基，氨基或苯基取代1到3次，或者R1A是C6或C10芳基，它可以选择地被卤素，氰基，硝基，（C1-6）烷基，O（C1-6）烷基，酰胺基，氨基或苯基取代1到3次；R2是（C5-6）环烷基，R3是环戊基；或其药用可接受的盐，用作HCV NS3蛋白酶的抑制剂。
• Inhibitors Of Hepatitis C Virus Protease, And Compositions And Treatments Using The Same
  申请人：Collins Raymond Michael

  公开号：US20070249637A1

  公开（公告）日：2007-10-25

  The present invention provides compounds of formula (I), (II) or (IV), or pharmaceutically acceptable salts and solvates thereof, which are useful as inhibitors of the Hepatitis C virus (HCV) protease enzyme and are also useful for the treatment of HCV infections in HCV-infected mammals, including humans. The present invention also provides pharmaceutical compositions comprising compounds of formula (I), (II) or (IV), their pharmaceutically acceptable salts and solvates. Furthermore, the present invention provides intermediate compounds and methods useful in the preparation of compounds of formulas (I), (II) and (IV).

  本发明提供了公式(I)、(II)或(IV)的化合物，以及其药学上可接受的盐和溶剂，这些化合物对丙型肝炎病毒(HCV)蛋白酶酶具有抑制作用，并且也可用于治疗HCV感染的哺乳动物，包括人类。本发明还提供了包含公式(I)、(II)或(IV)的化合物、其药学上可接受的盐和溶剂的制药组合物。此外，本发明还提供了中间体化合物和制备公式(I)、(II)和(IV)化合物的方法。
• Antiviral coumpounds
  申请人：Cho Aesop

  公开号：US20090257978A1

  公开（公告）日：2009-10-15

  The invention is related to anti-viral compounds, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

  本发明涉及抗病毒化合物、含有这些化合物的组合物和治疗方法，包括这些化合物的给药，以及用于制备这些化合物的有用过程和中间体。
• ANTIVIRAL COMPOUNDS
  申请人：Cho Aesop

  公开号：US20120190866A1

  公开（公告）日：2012-07-26

  The invention is related to anti-viral compounds, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

  本发明涉及抗病毒化合物、含有这些化合物的组合物以及包括这些化合物的治疗方法，以及用于制备这些化合物的过程和中间体。
• Antiviral compounds
  申请人：Cottell Jeromy J.

  公开号：US20090186869A1

  公开（公告）日：2009-07-23

  The invention is related to anti-viral compounds, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

  本发明涉及抗病毒化合物、含有该化合物的组合物以及包括该化合物的治疗方法，还涉及用于制备该化合物的过程和中间体。