Allyl 3-(cyano)-7-(S)-(t-butoxycarbonylamino)-8-oxo-1,5-diazabicyclo[3.3.0]octa-2-ene-2-carboxylate | 122332-43-8

• 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: Allyl 3-(cyano)-7-(S)-(t-butoxycarbonylamino)-8-oxo-1,5-diazabicyclo[3.3.0]octa-2-ene-2-carboxylate
• 英文别名: prop-2-enyl (2S)-6-cyano-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxo-2,7-dihydro-1H-pyrazolo[1,2-a]pyrazole-5-carboxylate
• CAS: 122332-43-8
• 化学式: C₁₆H₂₀N₄O₅
• 分子量: 348.359
• InChiKey: IEARVTKZJUGCHJ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Allyl 3-(cyano)-7-(S)-(t-butoxycarbonylamino)-8-oxo-1,5-diazabicyclo[3.3.0]octa-2-ene-2-carboxylate 在 N-甲基吗啉 、 盐酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 3.03h， 生成
  参考文献：
  名称：

  Structure-activity relationship within a series of pyrazolidinone antibacterial agents. 2. Effect of side-chain modification on in vitro activity and pharmacokinetic parameters

  摘要：

  The structure-activity relationship among a series of novel pyrazolidinone antibacterial agents is described. Specifically, the effect of modification of the side chain attached to the nitrogen at C-7 was explored in an attempt to improve the potency and spectrum of activity. This approach was successful in identifying several compounds having good in vitro profiles. These top candidates were then evaluated for their activity in vivo, and their pharmacokinetic behavior in various animal models was explored. This information proved critical for the identification of candidates for clinical evaluation.

  DOI：

  10.1021/jm00074a002
• 作为产物：
  描述：

  [2-((S)-4-tert-Butoxycarbonylamino-3-oxo-pyrazolidin-1-yl)-1-cyano-ethyl]-phosphonic acid diethyl ester 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 Allyl 3-(cyano)-7-(S)-(t-butoxycarbonylamino)-8-oxo-1,5-diazabicyclo[3.3.0]octa-2-ene-2-carboxylate
  参考文献：
  名称：

  [3.3.0]吡唑啉酮：一种新型合成抗菌剂的有效合成方法。

  摘要：

  描述了[3.3.0]稠合的吡唑烷酮的新颖合成。该方法依赖于已知吡唑烷酮单环的环氮的选择性逐步官能化。分子内Wadsworth-Horner-Emmons缩合产生所需的双环结构。从该途径制备的化合物已显示出强大的体外抗菌活性。

  DOI：

  10.1016/0040-4039(90)80153-d

文献信息

• TERNANSKY, ROBERT J.;DRAHEIM, SUSAN E., TETRAHEDRON LETT. , 31,(1990) N0, C. 2805-2808
  作者：TERNANSKY, ROBERT J.、DRAHEIM, SUSAN E.

  DOI：——

  日期：——
• US4795815A
  申请人：——

  公开号：US4795815A

  公开（公告）日：1989-01-03
• Structure-activity relationship within a series of pyrazolidinone antibacterial agents. 2. Effect of side-chain modification on in vitro activity and pharmacokinetic parameters
  作者：Robert J. Ternansky、Susan E. Draheim、Andrew J. Pike、Fred T. Counter、Judy A. Eudaly、Jeffrey S. Kasher

  DOI：10.1021/jm00074a002

  日期：1993.10

  The structure-activity relationship among a series of novel pyrazolidinone antibacterial agents is described. Specifically, the effect of modification of the side chain attached to the nitrogen at C-7 was explored in an attempt to improve the potency and spectrum of activity. This approach was successful in identifying several compounds having good in vitro profiles. These top candidates were then evaluated for their activity in vivo, and their pharmacokinetic behavior in various animal models was explored. This information proved critical for the identification of candidates for clinical evaluation.
• [3.3.0] Pyrazolodinones: An efficient synthesis of a new class of synthetic antibacterial agents.
  作者：Robert J. Ternansky、Susan E. Draheim

  DOI：10.1016/0040-4039(90)80153-d

  日期：1990.1

  A novel synthesis of [3.3.0] fused pyrazolidinones is described. The methodology relies on selective stepwise functionalization of the ring nitrogens of a known pyrazolidinone monocycle. Intramolecular Wadsworth-Horner-Emmons condensation gives rise to the desired bicyclic structure. The compounds prepared from this route have demonstrated potent antibacterial activity in vitro.

  描述了[3.3.0]稠合的吡唑烷酮的新颖合成。该方法依赖于已知吡唑烷酮单环的环氮的选择性逐步官能化。分子内Wadsworth-Horner-Emmons缩合产生所需的双环结构。从该途径制备的化合物已显示出强大的体外抗菌活性。