adamantan-1-yltrimethylsilanyloxy-acetonitrile | 79671-70-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: adamantan-1-yltrimethylsilanyloxy-acetonitrile
• 英文别名: Adamantan-1-yl-trimethylsilanyloxy-acetonitrile；2-(1-adamantyl)-2-trimethylsilyloxyacetonitrile
• CAS: 79671-70-8
• 化学式: C₁₅H₂₅NOSi
• 分子量: 263.455
• InChiKey: VKXUENGVQZSDFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  adamantan-1-yltrimethylsilanyloxy-acetonitrile 在 platinum(IV) oxide 盐酸 、 氨 、 氢气 作用下， 以 甲醇 为溶剂， 反应 21.0h， 生成 (RS)-1-(adamantan-1-yl)ethane-1,2-diamine
  参考文献：
  名称：

  Influence of an additional 2-amino substituent of the 1-aminoethyl pharmacophore group on the potency of rimantadine against influenza virus A

  摘要：

  We examined whether the incorporation of a second amino group into the 1-aminoethyl pharmacophore of rimantadine 2 and into the piperidine pharmacophore of the heterocyclic rimantadine 4 was compatible with anti-influenza virus A activity. The new synthetic molecules are capable of forming two hydrogen bonds within the receptor. We identified molecules 8 and 16, bearing the adamantyl and 1,2-diaminoethyl groups, which are equipotent to rimantadine 2 bearing the adamantyl and I-aminoethyl pharmacophore groups. Interestingly, diamino compound 16 is a 4-fold more potent inhibitor than its parent monoamino, heterocyclic rimantadine 4 propably because of additional hydrogen bonding interactions with the M2 protein receptor. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.092
• 作为产物：
  描述：

  1-金刚烷甲醇 在 pyridinium chlorochromate 、 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 生成 adamantan-1-yltrimethylsilanyloxy-acetonitrile
  参考文献：
  名称：

  芳环在肾上腺素胺中的重要性。5.作为苯基乙醇胺N-甲基转移酶抑制剂的苯基乙醇胺的非芳族类似物：疏水和空间相互作用的作用。

  摘要：

  DOI：

  10.1021/jm00133a003

文献信息

• Sorochinskii, A. E.; Aleksandrov, A. M.; Gamaleya, V. F., Journal of Organic Chemistry USSR (English Translation), 1981, p. 1461 - 1466
  作者：Sorochinskii, A. E.、Aleksandrov, A. M.、Gamaleya, V. F.、Kukhar', V. P.

  DOI：——

  日期：——
• Crystal Structures of Rat Vitamin D Receptor Bound to Adamantyl Vitamin D Analogs: Structural Basis for Vitamin D Receptor Antagonism and Partial Agonism
  作者：Makoto Nakabayashi、Sachiko Yamada、Nobuko Yoshimoto、Takashi Tanaka、Miharu Igarashi、Teikichi Ikura、Nobutoshi Ito、Makoto Makishima、Hiroaki Tokiwa、Hector F. DeLuca、Masato Shimizu

  DOI：10.1021/jm8004477

  日期：2008.9.11

  The X-ray crystal structures of the rat VDR ligand-binding domain complexed with 19-norvitamin D compound,, that contain an adamantyl substituent at the side-chain terminus, 2a (ADTT), 2b (ADNY), and 2c (ADMI4) and a coactivator peptide derived from DRIP205 are reported. These compounds show a series of partial agonistic (10-75% efficacy)/antagonistic activities. All of these complexed receptors are crystallized in the canonical active conformation, regardless of their activity profiles. The bulky adamantyl side chain does not crowd helix 12 but protrudes into the gap formed by helix 11, loop 11-12, helix 3, and loop 6-7, thereby widening the ligand binding pocket. We suggest that these structural changes destabilize the active protein conformation and reduce its contribution to equilibrium among the active and inactive conformations. The coactivator peptide traps the minor active conformation, and the equilibrium shifts to the active conformation. As a result, these ligands show partial agonistic activities.
• SOROCHINSKIJ A. E.; ALEKSANDROV A. M.; GAMALEYA V. F.; KUXAR V. P., ZH. ORGAN. XIMII, 1981, 17, HO 8, 1642-1648
  作者：SOROCHINSKIJ A. E.、 ALEKSANDROV A. M.、 GAMALEYA V. F.、 KUXAR V. P.

  DOI：——

  日期：——