3-azidohexahydro-2(1H)-azocinone | 81867-12-1

• 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: 3-azidohexahydro-2(1H)-azocinone
• 英文别名: 3-Azidohexahydro-2(1H)-azocinon；3-azidoperhydroazocin-2-one；3-azidoazocan-2-one
• CAS: 81867-12-1
• 化学式: C₇H₁₂N₄O
• 分子量: 168.198
• InChiKey: XAJUMZWRGXACJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  43.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-azidohexahydro-2(1H)-azocinone 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 (S)-1-<(tert-butoxycarbonyl)methyl>-3-aminoperhydroazocin-2-one
  参考文献：
  名称：

  Conformationally restricted inhibitors of angiotensin-converting enzyme. Synthesis and computations

  摘要：

  A series of inhibitors of angiotensin converting enzyme (ACE, dipeptidyl carboxypeptidase, EC 3.4.15.1) is described which addresses certain conformational aspects of the enzyme-inhibitor interaction. In this study the alanylproline portion of the potent ACE inhibitor enalaprilat (2) is replaced by a series of monocyclic lactams containing the required recognition and binding elements. In order to more fully assess the lactam ring conformations and the key backbone angle psi as defined in 3 with respect to possible enzyme-bound conformations, a series of model lactams was investigated with use of molecular mechanics. The results point to a correlation between inhibitor potency (IC50) and the computed psi angle for the lowest energy conformation of the model compounds. Thus the psi angle as defined in 3 is an important determinant in the binding of inhibitors to ACE. The inhibition data in conjunction with the computational data have served to define a window of psi angles from 130 degrees to 170 degrees which seems to be acceptable to the ACE active site.

  DOI：

  10.1021/jm00152a014
• 作为产物：
  描述：

  3-bromohexahydro-2(1H)-azocinone 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以48%的产率得到3-azidohexahydro-2(1H)-azocinone
  参考文献：
  名称：

  氨基噻唑衍生物。I.单环和稠合的5-氨基噻唑衍生物的方便合成

  摘要：

  结果表明，用五硫化二磷或Lawesson试剂处理α-氨基酸衍生的二酰胺可为制备5-氨基噻唑提供便利的方法。通过该方法，除了单环5-氨基噻唑19，新的双环5-氨基噻唑衍生物，如4,5,6,7-四氢噻唑并[5,4- b〕吡啶11，5,6,7,8-四氢-4- ħ -噻唑并[5,4- b ]吖庚因7，-4,5,6,7,8,9- hexahydrothiazolo并[5,4- b ]吖辛因16在中等制备到从简单的良好的产率和相关的化合物双酰胺，表明该方法具有广泛的通用性。

  DOI：

  10.1002/jhet.5570310432

文献信息

• Lactam inhibitors of factor Xa and method
  申请人：——

  公开号：US20020025957A1

  公开（公告）日：2002-02-28

  Lactam inhibitors are provided which have the structure 1 including pharmaceutically acceptable salts thereof and all stereoisomers thereof, and prodrug esters thereof, wherein n is 1 to 5; and and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 10a , 10 11 and R 12 are as defined herein. These compounds are inhibitors of Factor Xa and thus are useful as anticoagulants. A method for treating cardiovascular diseases associated with thromboses is also provided.

  提供了具有以下结构的内酰胺抑制剂 1 ，包括其药用可接受的盐及其所有立体异构体，以及其前药酯，其中n为1至5；和 和R 1 ，R 2 ，R 3 ，R 4 ，R 5 ，R 6 ，R 7 ，R 8 ，R 9 ，R 10 ，R 10a ，10 11 和R 12 如本文所定义。这些化合物是因子Xa的抑制剂，因此可用作抗凝剂。还提供了一种用于治疗与血栓相关的心血管疾病的方法。
• [EN] LACTAM INHIBITORS OF FACTOR XA AND METHOD<br/>[FR] INHIBITEURS DE LACTAMES DU FACTEUR XA ET PROCEDE ASSOCIE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2001096331A1

  公开（公告）日：2001-12-20

  Lactam inhibitors are provided which have the structure (I) including pharmaceutically acceptable salts thereof and all stereoisomers thereof, and prodrug esters thereof, wherein n is l to 5; and R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R10a, R11 and R12 are as defined herein. These compounds are inhibitors of Factor Xa and thus are useful as anticoagulants. A method for treating cardiovascular diseases associated with thromboses is also provided.

  提供了具有结构（I）的内酰胺抑制剂，包括其药学上可接受的盐和所有立体异构体，以及其前药酯，其中n为1至5; R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R10a、R11和R12如本文所定义。这些化合物是因子Xa的抑制剂，因此可用作抗凝剂。还提供了一种用于治疗与血栓有关的心血管疾病的方法。
• Substituted enantholactam derivatives as antihypertensives, a process for preparing and a pharmaceutical composition containing them, and intermediates
  申请人：Merck & Co., Inc.

  公开号：EP0046289A2

  公开（公告）日：1982-02-24

  The invention relates to enantholactam derivatives of the formula wherein R and R4 are hydroxy, lower alkoxy, lower alkenoxy, aryloxy, diloweralkylamino lower alkoxy, hydroxy, dihydroxy, and acylamino substituted lower alkoxy, acyloxy lower alkoxy, arloweralkoxy, amino, hydroxyamino; R' is hydrogen, alkyl of from 1 to 12 carbon atoms which include branched and cyclic and unsaturated alkyl groups, substituted loweralkyl, arloweralkyl, arloweralkenyl, heteroarlower alkyl or heteroarlower alkenyl, substituted arloweralkyl, or substituted heteroarlower alkyl, or substituted heteroarlower alkenyl, wherein the aryl or heteroaryl portion is substituted, substituted arloweralkyl or substituted heteroarloweralkyl wherein the alkyl portion can be substituted, R3 is hydrogen, lower alkyl, phenyl, substituted lower alkyl; and R2 is hydrogen, lower alkyl, cycloalkyl, aminoalkyl, hydroxyalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, or heterocycloalkyl, or substituted aryl. These compounds are useful as angiotensin converting enzyme inhibitors and antihypertensives. The invention relates also to a process for preparing these compounds.

  本发明涉及式中的庚内酰胺衍生物 式中 R和R4是羟基、低级烷氧基、低级烯氧基、芳氧基、稀低级烷基氨基低级烷氧基、羟基、二羟基和酰氨基取代的低级烷氧基、酰氧基低级烷氧基、低级烷氧基、氨基、羟基氨基； R' 是氢、1 至 12 个碳原子的烷基（包括支链、环状和不饱和烷基）、取代的低级烷基、低级烷基、低级烯基、杂低级烷基或杂低级烯基、取代的低级烷基或取代的杂低级烷基或取代的杂低级烯基（其中芳基或杂芳基部分被取代）、取代的低级烷基或取代的杂低级烷基（其中烷基部分可被取代）、 R3 是氢、低级烷基、苯基、取代的低级烷基；和 R2 是氢、低级烷基、环烷基、氨基烷基、羟基烷基、芳基、杂芳基、芳烷基、杂芳烷基、杂环烷基或取代的芳基。 这些化合物可用作血管紧张素转换酶抑制剂和降压药。本发明还涉及制备这些化合物的工艺。
• Beisswenger, Thomas; Effenberger, Franz, Chemische Berichte, 1984, vol. 117, # 4, p. 1513 - 1522
  作者：Beisswenger, Thomas、Effenberger, Franz

  DOI：——

  日期：——
• LACTAM INHIBITORS OF FACTOR XA AND METHOD
  申请人：Bristol-Myers Squibb Company

  公开号：EP1294716A1

  公开（公告）日：2003-03-26