2,5-diazido-2,5-dideoxy-1,6-di-O-phenyl-L-iditol | 211993-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,5-diazido-2,5-dideoxy-1,6-di-O-phenyl-L-iditol
• 英文别名: (2S,3R,4R,5S)-2,5-diazido-1,6-diphenoxyhexane-3,4-diol
• CAS: 211993-84-9
• 化学式: C₁₈H₂₀N₆O₄
• 分子量: 384.395
• InChiKey: PHZKUODZXVYKQF-WNRNVDISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  87.6
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,5-diazido-2,5-dideoxy-1,6-di-O-phenyl-L-iditol 在 palladium on activated charcoal 吡啶 、 chromium(VI) oxide 、 barium dihydroxide 、 sodium tetrahydroborate 、 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 、 乙酸酐 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 78.83h， 生成 4-Nitro-benzoic acid (1R,3R)-3-tert-butoxycarbonylamino-1-((S)-1-tert-butoxycarbonylamino-2-phenoxy-ethyl)-4-phenoxy-butyl ester
  参考文献：
  名称：

  HIV-1 Protease Inhibitors Based on Acyclic Carbohydrates

  摘要：

  A series of acyclic Ct-symmetric HIV protease inhibitors readily accessible from D-mannitol have been developed. Several of the compounds synthesized showed significant in vitro activity against HIV-1 protease.

  DOI：

  10.1021/jo971562c
• 作为产物：
  描述：

  2,5-diazido-2,5-dideoxy-3,4-O-isopropylidene-1,6-di-O-phenyl-L-iditol 在 乙酰氯 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以95%的产率得到2,5-diazido-2,5-dideoxy-1,6-di-O-phenyl-L-iditol
  参考文献：
  名称：

  新型有效的C2对称性疟原虫I和II抑制剂。

  摘要：

  已经合成了一系列含有C（2）对称核心结构的疟疾纤溶酶（Plm）I和II抑制剂，并测试了其蛋白酶抑制活性。这些化合物可以使用涉及二环氧的酚亲核开环的直接合成来制备。合成的示例化合物对Plm I和II均显示出显着的抑制活性，尤其是15c，其K（i）值分别为2.7nM和0.25nM，并且对组织蛋白酶D的选择性超过100倍。

  DOI：

  10.1016/s0968-0896(02)00643-0

文献信息

• Cyclic HIV-1 Protease Inhibitors Derived from Mannitol:  Synthesis, Inhibitory Potencies, and Computational Predictions of Binding Affinities
  作者：Johan Hultén、Nicholas M. Bonham、Ulrika Nillroth、Tomas Hansson、Guido Zuccarello、Abderrahim Bouzide、Johan Åqvist、Björn Classon、U. Helena Danielson、Anders Karlén、Ingemar Kvarnström、Bertil Samuelsson、Anders Hallberg

  DOI：10.1021/jm960728j

  日期：1997.3.1

  Ten C-2-symmetric cyclic urea and sulfamide derivatives have been synthesized from L-mannonic gamma-lactone and D-mannitol. The results of experimental measurement of their inhibitory potencies against HIV-1 protease were compared to calculated free energies of binding derived from molecular dynamics (MD) simulations. The compounds were selected, firstly, to enable elucidation of the role of stereochemistry for binding affinity (1a-d) and, secondly, to allow evaluation of the effects of variation in the link to the P1 and P1' phenyl groups on affinity (la and 2-5). Thirdly, compounds with hydrogen bond-accepting or -donating groups attached to the phenyl groups in the P2 and P2' side chains (6 and 7) were selected. Binding free energies were estimated by a linear response method, whose predictive power for estimating binding affinities from MD simulations was demonstrated.
• New potent C 2 -Symmetric malaria plasmepsin I and II inhibitors
  作者：Karin Oscarsson、Stefan Oscarson、Lotta Vrang、Elizabeth Hamelink、Anders Hallberg、Bertil Samuelsson

  DOI：10.1016/s0968-0896(02)00643-0

  日期：2003.4

  plasmepsin (Plm) I and II inhibitors containing a C(2)-symmetric core structure have been synthesised and tested for protease inhibition activity. These compounds can be prepared using a straightforward synthesis involving a phenol nucleophilic ring opening of a diepoxide. Exemplar compounds synthesised exhibited remarkable inhibitory activity against both Plm I and II, notably 15c with K(i) values of 2

  已经合成了一系列含有C（2）对称核心结构的疟疾纤溶酶（Plm）I和II抑制剂，并测试了其蛋白酶抑制活性。这些化合物可以使用涉及二环氧的酚亲核开环的直接合成来制备。合成的示例化合物对Plm I和II均显示出显着的抑制活性，尤其是15c，其K（i）值分别为2.7nM和0.25nM，并且对组织蛋白酶D的选择性超过100倍。
• HIV-1 Protease Inhibitors Based on Acyclic Carbohydrates
  作者：Guido Zuccarello、Abderrahim Bouzide、Ingemar Kvarnström、Gunilla Niklasson、Stefan C. T. Svensson、Magnus Brisander、Helena Danielsson、Ulrika Nillroth、Anders Karlén、Anders Hallberg、Björn Classon、Bertil Samuelsson

  DOI：10.1021/jo971562c

  日期：1998.7.1

  A series of acyclic Ct-symmetric HIV protease inhibitors readily accessible from D-mannitol have been developed. Several of the compounds synthesized showed significant in vitro activity against HIV-1 protease.