(2S,3R,5S)-2,5-diamino-1,6-diphenyl-hexan-3-ol | 144239-99-6

• 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: (2S,3R,5S)-2,5-diamino-1,6-diphenyl-hexan-3-ol
• 英文别名: (2S,3R,5S)-2,5-diamino-1,6-diphenylhexan-3-ol
• CAS: 144239-99-6
• 化学式: C₁₈H₂₄N₂O
• 分子量: 284.401
• InChiKey: BIZHLXOOWGXFLC-OKZBNKHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-羟基苯氧基乙酸 、 (2S,3R,5S)-2,5-diamino-1,6-diphenyl-hexan-3-ol 在 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-[(1S,3R,4S)-1-benzyl-3-hydroxy-4-[[2-(2-hydroxyphenoxy)acetyl]amino]-5-phenyl-pentyl]-2-(2-hydroxyphenoxy)acetamide
  参考文献：
  名称：

  Small hydroxyethylene-based peptidomimetics inhibiting both HIV-1 and C. albicans aspartic proteases

  摘要：

  We have extended a highly flexible method for rapidly assembling aspartic protease inhibitors to produce symmetric and asymmetric monohydroxyethylene peptidomimetics. This method is based on the prior synthesis of the central non-cleavable peptide-bond isostere [NH2-P(1psi)P1'-NH2; psi = hydroxyethylene isostere, HNCH(Bz)CHOHCH2CH(Bz)NH], with the possibility of accurately controlling its stereochemistry (S,S,S or S,R,S), and subsequently adding appropriate flanking units, chosen from commercially available amino acids, aromatic carboxylic acids, or phenoxyacetic acid (Poa) derivatives. The method was used to make asymmetric inhibitors of general formula Kyn-Xaa-PhepsiPhe-dmPoa, (Kyn = kynurenic acid, Xaa - Val, Thr or D-thienylglycine, M-r = 716-754) and symmetric inhibitors of formula xPoa-PhepsiPhe-xPoa (xPoa = Poa or dimethyl-, hydroxy-, formyl- or acetyl-Poa. Poa, M-r = 553-609). with logP(o/w). values ranging from 4.1 to 7.6. Inhibition of HIV-PR did not depend on the stereochemistry of the hydroxyl group, while it depended markedly on the substituents present on the Poa residues, with dmPoa being preferred over Poa or its more hydrophilic derivatives. Conversely, inhibition of Candida albicans Sap2 was higher for the S,S,S epimers, and Poa or its hydrophilic derivatives were preferred over dmPoa. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.004
• 作为产物：
  描述：

  (S,E)-tert-butyl 3-oxo-1,6-diphenylhex-4-en-2-ylcarbamate 在 palladium on activated charcoal sodium tetrahydroborate 、 sodium azide 、 18-冠醚-6 、 氢气 、 sodium hydride 、 caesium carbonate 、 三乙胺 、 间氯过氧苯甲酸 、 红铝 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 生成 (2S,3R,5S)-2,5-diamino-1,6-diphenyl-hexan-3-ol
  参考文献：
  名称：

  Small hydroxyethylene-based peptidomimetics inhibiting both HIV-1 and C. albicans aspartic proteases

  摘要：

  We have extended a highly flexible method for rapidly assembling aspartic protease inhibitors to produce symmetric and asymmetric monohydroxyethylene peptidomimetics. This method is based on the prior synthesis of the central non-cleavable peptide-bond isostere [NH2-P(1psi)P1'-NH2; psi = hydroxyethylene isostere, HNCH(Bz)CHOHCH2CH(Bz)NH], with the possibility of accurately controlling its stereochemistry (S,S,S or S,R,S), and subsequently adding appropriate flanking units, chosen from commercially available amino acids, aromatic carboxylic acids, or phenoxyacetic acid (Poa) derivatives. The method was used to make asymmetric inhibitors of general formula Kyn-Xaa-PhepsiPhe-dmPoa, (Kyn = kynurenic acid, Xaa - Val, Thr or D-thienylglycine, M-r = 716-754) and symmetric inhibitors of formula xPoa-PhepsiPhe-xPoa (xPoa = Poa or dimethyl-, hydroxy-, formyl- or acetyl-Poa. Poa, M-r = 553-609). with logP(o/w). values ranging from 4.1 to 7.6. Inhibition of HIV-PR did not depend on the stereochemistry of the hydroxyl group, while it depended markedly on the substituents present on the Poa residues, with dmPoa being preferred over Poa or its more hydrophilic derivatives. Conversely, inhibition of Candida albicans Sap2 was higher for the S,S,S epimers, and Poa or its hydrophilic derivatives were preferred over dmPoa. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.004

文献信息

• Retroviral protease inhibiting compounds
  申请人：ABBOTT LABORATORIES

  公开号：EP0486948A2

  公开（公告）日：1992-05-27

  A retroviral protease inhibiting compound of the formula A -X- B is disclosed. Also disclosed are a composition and method for inhibiting a retroviral protease and for treating an HIV infection. Also disclosed are processes and intermediates useful for the preparation of the retroviral protease inhibitors.

  本发明公开了一种式 A -X- B 的逆转录病毒蛋白酶抑制化合物。还公开了一种抑制逆转录病毒蛋白酶和治疗 HIV 感染的组合物和方法。还公开了用于制备逆转录病毒蛋白酶抑制剂的工艺和中间体。
• Intermediates for preparing retroviral protease inhibiting compounds
  申请人：Abbott Laboratories

  公开号：EP0997459A1

  公开（公告）日：2000-05-03

  An intermediate of the formula: and an intermediate of the formula: or an acid addition salt thereof.

  公式的中间体： 和 式的中间体 或其酸加成盐。
• Synthesis and Antimycobacterial Activity of Novel Amino Alcohols Containing Central Core of the Anti-HIV Drugs Lopinavir and Ritonavir
  作者：Claudia R. B. Gomes、Marcele Moreth、Danielle Cardinot、Valquiria Kopke、Wilson Cunico、Maria Cristina da Silva Lourenço、Marcus V. N. de Souza

  DOI：10.1111/j.1747-0285.2011.01244.x

  日期：2011.12

  Eleven new amino alcohol derivatives have been synthesized from reactions of lopinavir intermediate and heteroaromatic aldehyde in good yields. These compounds, the antiretrovirals (lopinavir and ritonavir) and lopinavir key intermediate were evaluated as antibacterial agents against Mycobacterium tuberculosis H37Rv using the Alamar Blue susceptibility test and their activity expressed as the minimum inhibitory concentration (MIC) in μm. Ten amino alcohols evaluated displayed significant activity (MIC between 6.15 and 108.4 μm) when compared to first‐line drug ethambutol (MIC = 15.9 μm). Three of them showed more activity than ethambutol (MIC = 6.15; 6.21 and 13.4 μm). The appreciable activity of these compounds can be considered an important finding for the rational design of new leads for anti‐TB compounds.
• US5354866A
  申请人：——

  公开号：US5354866A

  公开（公告）日：1994-10-11
• US5541334A
  申请人：——

  公开号：US5541334A

  公开（公告）日：1996-07-30