(S)-2-<(tert-butoxycarbonyl)amino>-3-(phenylthio)propionic acid | 161448-74-4

• 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: (S)-2-<(tert-butoxycarbonyl)amino>-3-(phenylthio)propionic acid
• 英文别名: Boc-(S)-phenyl-D-Cys；(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylsulfanylpropanoic acid
• CAS: 161448-74-4
• 化学式: C₁₄H₁₉NO₄S
• 分子量: 297.375
• InChiKey: IBEVTCWKECBMJF-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-<(tert-butoxycarbonyl)amino>-3-(phenylthio)propionic acid 在 1-羟基苯并三唑一水物 、 三乙胺 、 间氯过氧苯甲酸 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (S)-N-(1S,2R)-<3-<2-<<(1,1-dimethylethyl)amino>carbonyl>phenyl>-2-hydroxy-1-(phenylmethyl)propyl>-2-<(methylsulfonyl)amino>-3-(phenylsulfinyl)propanamide
  参考文献：
  名称：

  Potent Human Immunodeficiency Virus Type 1 Protease Inhibitors That Utilize Noncoded d-Amino Acids as P₂/P₃ Ligands

  摘要：

  Noncoded D-amino acids have been designed to replace the quinaldic amide-asparaginyl moiety (P-2/P-3 ligand) found in several potent human immunodeficiency virus (HIV) protease inhibitors such as LY289612. The substituted nitrogen, optimally an N-methanesulfonyl moiety, served as a CH2CONH2 (asparagine side chain mimic), while the amino acid side chain became the backbone and P-3 ligand of these novel inhibitors. Compounds derived from S-aryl-D-cysteine proved to be patent HIV protease inhibitors which also exhibited potent whole cell antiviral activity. Oxidation of the cysteines to the sulfoxide or sulfone oxidation states resulted in significant improvements in potency. For example, the compound derived from N-(methylsulfonyl)-2-S-naphthylcysteine sulfone, 17c, was a 3.5 nM inhibitor of HIV protease which inhibited the spread of virus in MT4 cells with an IC50 = 4.3 nM. Compounds 17c,g,i were found to be orally bioavailable in a rat model.

  DOI：

  10.1021/jm950576c
• 作为产物：
  描述：

  N-叔丁氧羰基-D-丝氨酸(Β-内酯) 、 苯硫酚 在 sodium hydride 作用下， 生成 (S)-2-<(tert-butoxycarbonyl)amino>-3-(phenylthio)propionic acid
  参考文献：
  名称：

  Potent Human Immunodeficiency Virus Type 1 Protease Inhibitors That Utilize Noncoded d-Amino Acids as P₂/P₃ Ligands

  摘要：

  Noncoded D-amino acids have been designed to replace the quinaldic amide-asparaginyl moiety (P-2/P-3 ligand) found in several potent human immunodeficiency virus (HIV) protease inhibitors such as LY289612. The substituted nitrogen, optimally an N-methanesulfonyl moiety, served as a CH2CONH2 (asparagine side chain mimic), while the amino acid side chain became the backbone and P-3 ligand of these novel inhibitors. Compounds derived from S-aryl-D-cysteine proved to be patent HIV protease inhibitors which also exhibited potent whole cell antiviral activity. Oxidation of the cysteines to the sulfoxide or sulfone oxidation states resulted in significant improvements in potency. For example, the compound derived from N-(methylsulfonyl)-2-S-naphthylcysteine sulfone, 17c, was a 3.5 nM inhibitor of HIV protease which inhibited the spread of virus in MT4 cells with an IC50 = 4.3 nM. Compounds 17c,g,i were found to be orally bioavailable in a rat model.

  DOI：

  10.1021/jm950576c

文献信息

• [EN] CERTAIN GLYCINE DERIVATIVES AS FACTOR XA INHIBITORS FOR USE IN THE TREATMENT OF THROMBOTIC DISORDERS<br/>[FR] DERIVES DE GLYCINE FONCTIONNANT COMME INHIBITEURS DE XA DESTINES AU TRAITEMENT DES TROUBLES THROMBOTIQUES
  申请人：LILLY CO ELI

  公开号：WO2003049735A1

  公开（公告）日：2003-06-19

  Compounds of formula (I) in which R, R1, R2, n and X1 have the meanings given in the specification are factor Xa inhibitors useful in the treatment of thrombotic disorders.

  式(I)中R、R1、R2、n和X1的含义如规范中所述的化合物是Xa因子抑制剂，可用于治疗血栓性疾病。
• Certain glycine derivatives as factor xa inhibitors for use in the treatment of thrombotic disorders
  申请人：——

  公开号：US20040249155A1

  公开（公告）日：2004-12-09

  Compounds of formula (I) 1 in which R, R 1 , R 2 , n and X 1 have the meanings given in the specification are Factor Xa inhibitors useful in the treatment of thrombotic disorders.

  化学式为(I)1的化合物，其中R、R1、R2、n和X1的含义如规范中所述，是在治疗血栓性疾病中有用的因子Xa抑制剂。
• CERTAIN GLYCINE DERIVATIVES AS FACTOR Xa INHIBITORS FOR USE IN THE TREATMENT OF THROMBOTIC DISORDERS
  申请人：Wiley Robert Michael

  公开号：US20070072869A1

  公开（公告）日：2007-03-29

  Compounds of formula (I) in which R, R 1 , R 2 , n and X 1 have the meanings given in the specification are Factor Xa inhibitors useful in the treatment of thrombotic disorders.

  式(I)中的化合物，其中R、R1、R2、n和X1的含义如规范中所述，是治疗血栓性疾病有用的Xa因子抑制剂。
• CERTAIN GLYCINE DERIVATIVES AS FACTOR XA INHIBITORS FOR USE IN THE TREATMENT OF THROMBOTIC DISORDERS
  申请人：ELI LILLY AND COMPANY

  公开号：EP1455787A1

  公开（公告）日：2004-09-15
• US7078415B2
  申请人：——

  公开号：US7078415B2

  公开（公告）日：2006-07-18