3-(benzyloxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyl-5-(iodomethyl)-(4S,5S)-1,3-oxazolidine | 114469-19-1

• 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: 3-(benzyloxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyl-5-(iodomethyl)-(4S,5S)-1,3-oxazolidine
• 英文别名: 3-Benzyloxycarbonyl-4(S)-cyclohexylmethyl-2,2-dimethyl-5(S)-iodomethyl-oxazolidine；benzyl (4S,5S)-4-(cyclohexylmethyl)-5-(iodomethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 114469-19-1
• 化学式: C₂₁H₃₀INO₃
• 分子量: 471.379
• InChiKey: MREJRPXVWPOULN-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(benzyloxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyl-5-(iodomethyl)-(4S,5S)-1,3-oxazolidine 、 异戊酸 生成 (2RS)-2-[(4S,5S)-3-benzyloxycarbonyl-4-cyclohexylmethyl-2,2-dimethyl-1,3-oxazolidin-5-yl]methyl-3-methylbutanoic acid
  参考文献：
  名称：

  BRADBURY, ROBERT H.;MAJOR, JOHN S.;OLDHAM, ALEC A.;RIVETT, JANET E.;ROBER+, J. MED. CHEM., 33,(1990) N, C. 2335-2342

  摘要：

  DOI：
• 作为产物：
  描述：

  3-<(benzyloxycarbonyl)amino>-4-cyclohexyl-1-iodo-2-<(trimethylsilyl)oxy>-(2R,3S)-butane 在 potassium fluoride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 3-(benzyloxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyl-5-(iodomethyl)-(4S,5S)-1,3-oxazolidine
  参考文献：
  名称：

  Synthesis and biological activity of some transition-state inhibitors of human renin

  摘要：

  A series of renin inhibitors containing the dipeptide transition state mimics (2S,4S,5S)-5-amino-4-hydroxy-2-isopropyl-7-methyloctanoic acid (Leu (OH)/Val) and (2S,4S,5S)-5-amino-4-hydroxy-2-isopropyl-6-cyclohexylhexanoic acid (CHa /(OH)/Val) was prepared. A structure-activity study with Boc-Phe-His-Leu (OH)/Val-Ile-His-NH2 (8a) as starting material led to N-[(2S)-2-[(tert-butylsulfonyl)methyl]-3-phenylpropionyl]-His-Cha (OH)/ Val- NHC4H9-n (8i) which has the length of a tetrapeptide and contains only one natural amino acid. Compound 8i had an IC50 of 2 x 10(-9) M against human renin and showed high enzyme specificity; IC50 values against the related aspartic proteinases pepsin and cathepsin D were (8 x 10(-6) and 3 x 10(-6) M, respectively). In salt-depleted marmosets, 8i inhibited plasma renin activity PRA and lowered blood pressure for up to 2 h after oral administration of a dose of 10 mg/kg.

  DOI：

  10.1021/jm00117a027

文献信息

• Peptides retroviral protease inhibitors comprising
  申请人：——

  公开号：US05145951A1

  公开（公告）日：1992-09-08

  Antiviral peptides of the formula ##STR1## in which W is an amino protecting group, A,B,D,E and L each independently is a direct bond, or a radical of the formula ##STR2## R.sup.1 and R.sup.2 each independently is cycloakyl or optionally substituted alkyl or alkenyl, Y is --NHR.sup.10, and R.sup.10 is cycloalkyl or optionally substituted alkyl, and their physiologically acceptable salts. The formula includes a 2-amino-2-methylpropionic acid (AiB) residue, which may optionally be protected, as the N-terminal .alpha.-amino acid. The peptides are expected to be useful as medicaments, in particular as antiviral agents in human and veterinary medicine. The peptides are shown to inhibit aspartyl proteases including human immunodeficiency virus (HIV) protease, to have anti-HIV activity and to inhibit the proliferation of HIV in HIV-I infected human lymphocytes. The peptides are expected to be useful in treating patients having HIV related disorders such as ARC and AIDS.

  公式为 ##STR1## 的抗病毒肽，其中W是氨基保护基，A、B、D、E和L各自独立地是直接键或式中的基团 ##STR2## R1和R2各自独立地是环烷基或可选取代的烷基或烯基，Y为--NHR10，R10为环烷基或可选取代的烷基，并且它们的生理上可接受的盐。该公式包括2-氨基-2-甲基丙酸（AiB）残基，可选择性地作为N-末端α-氨基酸进行保护。预计这些肽将用作药物，特别是作为人类和兽医医学中的抗病毒剂。已经证明这些肽能够抑制天冬氨酸蛋白酶，包括人类免疫缺陷病毒（HIV）蛋白酶，具有抗HIV活性并抑制HIV在HIV-I感染的人类淋巴细胞中的增殖。预计这些肽将有助于治疗患有HIV相关疾病，如ARC和AIDS的患者。
• Neue Peptide, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel, insbesondere als Arzneimittel gegen Retroviren
  申请人：BAYER AG

  公开号：EP0437729A2

  公开（公告）日：1991-07-24

  Die Erfindung betrifft neue Peptide, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel, insbesondere als antivirale Mittel in der Human- und Tiermedizin.

  本发明涉及新的多肽、其制备工艺及其作为药物的用途，特别是作为人类和兽医的抗病毒剂。
• RADDATZ, PETER;SCHMITGES, CLAUS J.;MINCK, KLAUS OTTO
  作者：RADDATZ, PETER、SCHMITGES, CLAUS J.、MINCK, KLAUS OTTO

  DOI：——

  日期：——
• US5145951A
  申请人：——

  公开号：US5145951A

  公开（公告）日：1992-09-08