N-[(tert-butyloxy)carbonyl]-S-(chloromethyl)-D-cysteine methyl ester | 126645-23-6

• 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: N-[(tert-butyloxy)carbonyl]-S-(chloromethyl)-D-cysteine methyl ester
• 英文别名: Methyl 3-(chloromethylsulfanyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 126645-23-6
• 化学式: C₁₀H₁₈ClNO₄S
• 分子量: 283.776
• InChiKey: NSMKIMADRSVCKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[(tert-butyloxy)carbonyl]-S-(chloromethyl)-D-cysteine methyl ester 在 potassium fluoride 、 四丁基氯化铵 、 sodium hydride 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 12.5h， 生成 tert-butyl N-[(2R,3R)-7-oxa-5-thia-8,18-diazatetracyclo[9.7.0.02,8.012,17]octadeca-1(11),12,14,16-tetraen-3-yl]carbamate
  参考文献：
  名称：

  Intramolecular Pictet-Spengler reaction of N-alkoxytryptamines. 3. Stereoselective synthesis of (-)-debromoeudistomin L and (-)-O-methyldebromoeudistomin E and their stereoisomers

  摘要：

  DOI：

  10.1021/jo00300a011
• 作为产物：
  描述：

  N-叔丁氧羰基-O-对甲苯磺酰基丝氨酸甲酯 在 氢氧化钾 、 苄基三乙基氯化铵 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[(tert-butyloxy)carbonyl]-S-(chloromethyl)-D-cysteine methyl ester
  参考文献：
  名称：

  Intramolecular Pictet-Spengler reaction of N-alkoxytryptamines. 3. Stereoselective synthesis of (-)-debromoeudistomin L and (-)-O-methyldebromoeudistomin E and their stereoisomers

  摘要：

  DOI：

  10.1021/jo00300a011

文献信息

• Antiviral and tumor cell antiproliferative SAR studies on tetracyclic eudistomins—II
  作者：Jan H. van Maarseveen、Hans W. Scheeren、Erik De Clercq、Jan Balzarini、Chris G. Kruse

  DOI：10.1016/s0968-0896(97)00034-5

  日期：1997.5

  In a search for the minimum pharmacophore of the naturally occurring tetracyclic eudistomins, five structural analogues (4-8) were evaluated for their in vitro antiviral and tumor cell antiproliferative activities. For the synthesis of these derivatives both intra- and intermolecular Pictet-Spengler reactions have been used. Opening of the beta-carboline annulated 7-membered D-ring in 6 and 7 resulted in a complete loss of activity. On the other rand, replacement of either the oxygen atom or the sulfur atom in the 7-membered ring by a methylene group in 5 and 8, respectively, is allowed. These results combined with previous SAR data underline the crucial importance of the D-ring in eudistomins as a scaffold for the correct positioning of both basic nitrogen atoms. Also bioisosteric replacement of the bicyclic indole system with a dimethoxyphenyl group, to give the isoquinoline skeleton, is allowed. The tricyclic isoquinoline derivative 4 is, so far, the most promising antiviral analogue; it combines a high potency (MIG at 100 ng/mL (340 nM)) with high MCC/MIC ratios (ranging from 1000 to 5000 against HSV-1, HSV-2, vaccinia virus, and vesicular stomatitis virus). (C) 1997 Elsevier Science Ltd.
• Antiviral and antitumor structure-activity relationship studies on tetracyclic eudistomines
  作者：Jan H. Van Maarseveen、Pedro H. H. Hermkens、Erik De Clercq、Jan Balzarini、Hans W. Scheeren、Chris G. Kruse

  DOI：10.1021/jm00095a019

  日期：1992.8

  The in vitro antiviral and antitumor activities of (-)-debromoeudistomin K (1a) and 10 structural analogues (1b-1j and 11) were evaluated. The synthesis was accomplished with an intramolecular Pictet-Spengler condensation reaction as the key step. This examination revealed some structural and stereochemical features that are important for both the antiviral and antitumor activities. The most striking points for activity are the necessity to have the correct natural stereochemistry at both C(1) and C(13b) and the presence of the C(1)-NH2 substituent. As was revealed before with naturally isolated eudistomins a substituent in the indole ring greatly influences the biological activity. The 5-OMe derivative Ih shows high potency in both antiviral and antitumor models.