2-甲基-2-丙基2-(3-呋喃甲基)肼羧酸酯 | 150767-03-6

• 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
• 中文名称: 2-甲基-2-丙基2-(3-呋喃甲基)肼羧酸酯
• 中文别名: 哌嗪2-(1-哌啶基甲基)-(9CI)
• 英文名称: N¹-<(tert-butyloxy)carbonyl>-N²-(3-furanylmethyl)hydrazine
• 英文别名: (tert-butoxy)-N-[(3-furylmethyl)amino]carboxamide；tert-Butyl 2-(furan-3-ylmethyl)hydrazinecarboxylate；tert-butyl N-(furan-3-ylmethylamino)carbamate
• CAS: 150767-03-6
• 化学式: C₁₀H₁₆N₂O₃
• 分子量: 212.249
• InChiKey: GWONYTFZFBNWIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-甲基-2-丙基2-(3-呋喃甲基)肼羧酸酯 在 甲烷磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 生成 7-chloro-4-hydroxy-2-(furan-3-ylmethyl)-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione
  参考文献：
  名称：

  Pyridazinoquinolinetriones as NMDA Glycine-Site Antagonists with Oral Antinociceptive Activity in a Model of Neuropathic Pain

  摘要：

  A series of 7-chloro-2,3-dihydro-2-[1-(pyridinyl)alkyl]-pyridazino[4,5-b]quinoline-1,4,10(5H)-triones were synthesized and found to have potent activity at the glycine site of the NMDA receptor. In some cases, these compounds possessed poor aqueous solubility that may have contributed to poor rat oral bioavailability. Subsequently, compounds have been identified with improved aqueous solubility and oral bioavailability. Several of these compounds were examined in a rat chronic constrictive injury (CCI) model of neuropathic pain and found to have potent activity when dosed orally.

  DOI：

  10.1021/jm060212s
• 作为产物：
  描述：

  2-甲基-2-丙基(2E)-2-(3-呋喃基亚甲基)肼羧酸酯 在 palladium on activated charcoal 氢气 作用下， 生成 2-甲基-2-丙基2-(3-呋喃甲基)肼羧酸酯
  参考文献：
  名称：

  轻松合成含有新型伪对称二肽等排体的有效HIV-1蛋白酶抑制剂

  摘要：

  通过用各种取代的肼将受保护的环氧化物开环，合成了一系列含有新型伪对称二肽等位基因3的有效的HIV-1蛋白酶抑制剂。

  DOI：

  10.1039/c39930001052

文献信息

• Facile synthesis of potent HIV-1 protease inhibitors containing a novel pseudo-symmetric dipeptide isostere
  作者：Hing L. Sham、David A. Betebenner、Chen Zhao、Norman E. Wideburg、Ayda Saldivar、Dale J. Kempf、Jacob J. Plattner、Daniel W. Norbeck

  DOI：10.1039/c39930001052

  日期：——

  A series of potent inhibitors of the HIV-1 protease containing a novel pseudo-symmetric dipeptide isostere 3 was synthesized via ring opening of a protected epoxide with various substituted hydrazines.

  通过用各种取代的肼将受保护的环氧化物开环，合成了一系列含有新型伪对称二肽等位基因3的有效的HIV-1蛋白酶抑制剂。
• A Novel, Picomolar Inhibitor of Human Immunodeficiency Virus Type 1 Protease
  作者：Hing L. Sham、Chen Zhao、Kent D. Stewart、David A. Betebenner、Shuqun Lin、Chang H. Park、Xiang-P. Kong、William Rosenbrook、Thomas Herrin、Darold Madigan、Suthida Vasavanonda、Nicholas Lyons、Akhter Molla、Ayda Saldivar、Kennan C. Marsh、Edith McDonald、Norman E. Wideburg、Jon F. Denissen、Terrel Robins、Dale J. Kempf、Jacob J. Plattner、Daniel W. Norbeck

  DOI：10.1021/jm9507183

  日期：1996.1.1

  The design, synthesis, and molecular modeling studies of a novel series of azacyclic ureas, which are inhibitors of human immunodeficiency virus type 1 (HIV-1) protease that incorporate different ligands for the S1', S2, and S2' substrate-binding sites of HIV-1 protease are described. The synthesis of this series is highly flexible in the sense that the P1', P2, and P2' residues of the inhibitors can be changed independently. Molecular modeling studies on the phenyl ring of the P2 and P2' ligand suggested incorporation of hydrogen-bonding donor/acceptor groups at the 3' and 4-positions of the phenyl ring should increase binding potency. This led to the discovery of compound 7f (A-98881), which possesses high potency in the HIV-1 protease inhibition assay and the in vitro MT-4 cell culture assay (Ki = approximately 5 pM and EC50 = 0.002 microM). This compares well with the symmetrical cyclic urea 1 pioneered at DuPont Merck.
• Pyridazinoquinolinetriones as NMDA Glycine-Site Antagonists with Oral Antinociceptive Activity in a Model of Neuropathic Pain
  作者：Thomas M. Bare、Dean G. Brown、Carey L. Horchler、Megan Murphy、Rebecca A. Urbanek、Vernon Alford、Christine Barlaam、Martin C. Dyroff、James B. Empfield、Janet M. Forst、Keith J. Herzog、Richard A. Keith、Alan S. Kirschner、Chi-Ming C. Lee、Joseph Lewis、Frances M. McLaren、Kathy L. Neilson、Gary B. Steelman、Shephali Trivedi、Edward P. Vacek、Wenhua Xiao

  DOI：10.1021/jm060212s

  日期：2007.6.1

  A series of 7-chloro-2,3-dihydro-2-[1-(pyridinyl)alkyl]-pyridazino[4,5-b]quinoline-1,4,10(5H)-triones were synthesized and found to have potent activity at the glycine site of the NMDA receptor. In some cases, these compounds possessed poor aqueous solubility that may have contributed to poor rat oral bioavailability. Subsequently, compounds have been identified with improved aqueous solubility and oral bioavailability. Several of these compounds were examined in a rat chronic constrictive injury (CCI) model of neuropathic pain and found to have potent activity when dosed orally.