N¹-(3-benzyloxycarbonylaminopropoxy)-N²,N³-di-tert-butyloxycarbonylguanidine | 226569-25-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N¹-(3-benzyloxycarbonylaminopropoxy)-N²,N³-di-tert-butyloxycarbonylguanidine
• 英文别名: 3-[N,N'-di-(tert-butyloxycarbonyl)]guanidinooxy-1-(benzyloxycarbonyl)aminopropane；[N,N'-di(tert-butoxycarbonyl)]3-(benzyloxycarbonylamino)-1-propoxyguanidine；benzyl N-[3-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]oxypropyl]carbamate
• CAS: 226569-25-1
• 化学式: C₂₂H₃₄N₄O₇
• 分子量: 466.535
• InChiKey: PXAOMLRMFQLPAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  137
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N¹-(3-benzyloxycarbonylaminopropoxy)-N²,N³-di-tert-butyloxycarbonylguanidine 在 palladium 10% on activated carbon 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.5h， 以28%的产率得到[N,N'-di(tert-butoxycarbonyl)]3-amino-1-propoxyguanidine
  参考文献：
  名称：

  Heteroaryl aminoguanidines and alkoxyguanidines and their use as protease inhibitors

  摘要：

  描述了氨基胍和烷氧基胍化合物，包括式VII的化合物： 其中X为O或NR9，Het，R1，R7，R8，R12-R15，Ra，Rb，Rc，Z和n在说明书中列出，以及其水合物，溶剂合物或药学上可接受的盐，其抑制蛋白酶如凝血酶。还描述了制备这种化合物的方法。该发明的化合物是蛋白酶的有效抑制剂，特别是类似胰蛋白酶的丝氨酸蛋白酶，如胰蛋白酶、凝血酶、纤溶酶和Xa因子。某些化合物通过直接、选择性地抑制凝血酶表现出抗血栓活性。该发明包括一种用于在哺乳动物中抑制血小板丢失、抑制血小板聚集物形成、抑制纤维蛋白形成、抑制血栓形成和抑制栓塞形成的组合物，包括一种该发明的化合物在药学上可接受的载体中。该发明的化合物的其他用途是作为抗凝剂，嵌入或物理上连接到用于血液采集、血液循环和血液储存设备的材料中，如导管、血液透析机、血液采集注射器和管道、血管内支架。此外，这些化合物可以被检测标记并用于体内血栓的成像。

  公开号：

  US06350764B2
• 作为产物：
  描述：

  3-aminooxy-1-(N-benzyloxycarbonyl)aminopropane 、 1,3-二-BOC-2-(三氟甲基磺酰)胍 在 三乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 24.0h， 以88%的产率得到N¹-(3-benzyloxycarbonylaminopropoxy)-N²,N³-di-tert-butyloxycarbonylguanidine
  参考文献：
  名称：

  New Charge-Deficient Agmatine Analogues

  摘要：

  N,N'-Di-Boc-N''-三氟甲胍被证明是 O-取代羟胺的有效胍基化试剂。 N-(3-氨基氧基丙基)-和N-(3-氨基丙氧基)胍是以前未知的等排和缺电荷胍丁胺类似物，现已合成。讨论了使用这些化合物研究多胺代谢的可能性。

  DOI：

  10.1007/s11171-005-0080-y

文献信息

• New Charge-Deficient Agmatine Analogues
  作者：A. R. Simonyan、N. A. Grigorenko、J. Vepsalainen、A. R. Khomutov

  DOI：10.1007/s11171-005-0080-y

  日期：2005.11

  N,N′-Di-Boc-N″-triflylguanidine was demonstrated to be an efficient guanidinylation reagent for O-substituted hydroxylamines. N-(3-Aminooxypropyl)- and N-(3-aminopropoxy)guanidines, previously unknown isosteric and charge-deficient agmatine analogues, have been synthesized. The possibilities of using these compounds in studying polyamine metabolism are discussed.

  N,N'-Di-Boc-N''-三氟甲胍被证明是 O-取代羟胺的有效胍基化试剂。 N-(3-氨基氧基丙基)-和N-(3-氨基丙氧基)胍是以前未知的等排和缺电荷胍丁胺类似物，现已合成。讨论了使用这些化合物研究多胺代谢的可能性。
• Novel convenient synthesis of biologically active esters of hydroxylamine
  作者：Maxim A. Khomutov、Swati Mandal、Janne Weisell、Neiha Saxena、Alina R. Simonian、Jouko Vepsalainen、Rentala Madhubala、Sergey N. Kochetkov

  DOI：10.1007/s00726-009-0410-0

  日期：2010.2

  Alkylation of ethyl N-hydroxyacetimidate with readily available methanesulfonates of functionally substituted alcohols and subsequent deprotection of aminooxy group is a novel and convenient method to prepare functionally substituted esters of hydroxylamine with high overall yield. This approach is a good alternative to well-known reaction of N-hydroxyphthalimide with alcohols under the Mitsunobu conditions. The properties of ethoxyethylidene protection of aminooxy group on the contrary to that of N-alkoxyphthalimide group allow to perform a wide spectra of the transformations in the radical of N-protected hydroxylamine derivatives. This is essential for synthetic strategies consisting in the introduction of N-protected aminooxy group at one of the first steps of synthesis and subsequent transformations of the radical.The inhibitory effect of one of the newly synthesized compound, 1-guanidinooxy-3-aminopropane (GAPA), was compared with that of well-known inhibitors of ornithine decarboxylase namely, alpha-difluoromethylornithine (DFMO) and 1-aminooxy-3-aminopropane (APA) on Leishmania donovani, a protozoan parasite that causes visceral leishmaniasis. GAPA, on the contrary with APA and DFMO, in micromolar concentrations, inhibited the growth of both amastigotes and promastigotes of sodium antimony gluconate-resistant forms of L. donovani.
• US7402586B2
  申请人：——

  公开号：US7402586B2

  公开（公告）日：2008-07-22
• Heteroaryl aminoguanidines and alkoxyguanidines and their use as protease inhibitors
  申请人：3-Dimensional Pharmaceuticals, Inc.

  公开号：US06350764B2

  公开（公告）日：2002-02-26

  Aminoguanidine and alkoxyguanidine compounds are described, including compounds of the Formula VII: wherein X is O or NR9 and Het, R1, R7, R8, R12-R15, Ra, Rb, Rc, Z, and n are set forth in the specification, as well as hydrates, solvates or pharmaceutically acceptable salts thereof, that inhibit proteolytic enzymes such as thrombin. Also described are methods for preparing such compounds. The compounds of the invention are potent inhibitors of proteases, especially trypsin-like serine proteases, such as chymotrypsin, trypsin, thrombin, plasmin and factor Xa. Certain of the compounds exhibit antithrombotic activity via direct, selective inhibition of thrombin. The invention includes a composition for inhibiting loss of blood platelets, inhibiting formation of blood platelet aggregates, inhibiting formation of fibrin, inhibiting thrombus formation, and inhibiting embolus formation in a mammal, comprising a compound of the invention in a pharmaceutically acceptable carrier. Other uses of compounds of the invention are as anticoagulants either embedded in or physically linked to materials used in the manufacture of devices used in blood collection, blood circulation, and blood storage, such as catheters, blood dialysis machines, blood collection syringes and tubes, blood lines and stents. Additionally, the compounds can be detectably labeled and employed for in vivo imaging of thrombi.

  描述了氨基胍和烷氧基胍化合物，包括式VII的化合物： 其中X为O或NR9，Het，R1，R7，R8，R12-R15，Ra，Rb，Rc，Z和n在说明书中列出，以及其水合物，溶剂合物或药学上可接受的盐，其抑制蛋白酶如凝血酶。还描述了制备这种化合物的方法。该发明的化合物是蛋白酶的有效抑制剂，特别是类似胰蛋白酶的丝氨酸蛋白酶，如胰蛋白酶、凝血酶、纤溶酶和Xa因子。某些化合物通过直接、选择性地抑制凝血酶表现出抗血栓活性。该发明包括一种用于在哺乳动物中抑制血小板丢失、抑制血小板聚集物形成、抑制纤维蛋白形成、抑制血栓形成和抑制栓塞形成的组合物，包括一种该发明的化合物在药学上可接受的载体中。该发明的化合物的其他用途是作为抗凝剂，嵌入或物理上连接到用于血液采集、血液循环和血液储存设备的材料中，如导管、血液透析机、血液采集注射器和管道、血管内支架。此外，这些化合物可以被检测标记并用于体内血栓的成像。