(R)-2-Amino-3-(4-dimethylamino-benzylsulfanyl)-propionic acid | 42727-83-3

• 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: (R)-2-Amino-3-(4-dimethylamino-benzylsulfanyl)-propionic acid
• 英文别名: (2R)-2-amino-3-[[4-(dimethylamino)phenyl]methylsulfanyl]propanoic acid
• CAS: 42727-83-3
• 化学式: C₁₂H₁₈N₂O₂S
• 分子量: 254.353
• InChiKey: GUMKPZKEHVWEJX-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  91.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-2-Amino-3-(4-dimethylamino-benzylsulfanyl)-propionic acid 在 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 SA6541
  参考文献：
  名称：

  Involvement of Leukotriene B4 in Murine Dermatitis Models

  摘要：

  Leukotriene B-4 (LTB4) is a product of the 5-lipoxygenase pathway of arachidonic acid (AA) metabolism. LTB4 is a potent chemotactic factor for neutrophils and has been postulated to play an important role in a variety of pathological conditions including rheumatoid arthritis, psoriasis, and inflammatory bowel disease. To investigate the role of LTB4 in dermatitis, we used S-(4-dimethylaminobenzyl)-N-[(2S) -mercapto-2-methylpropionyl]-L-cysteine (SA6541), a potent leukotriene A(4) (LTA(4)) hydrolase inhibitor. SA6541 inhibited LTB4 production with an IC50 value of 270 nM in vitro. 5-Hydroperoxyeicosatetraenoic acid (5-HPETE) or AA injection induced LTB4 production and neutrophil influx in mouse ear. SA6541 inhibited 5-HPETE- and AA-induced LTB4 production and neutrophil influx in mouse ear when administered orally at a dose of 50 mg/kg. SA6541 also inhibited 5-HPETE induced prostaglandin E-2 (PGE(2)) production, probably by an indirect effect through the inhibition of LTB4 production. These results suggest that LTB4 map be important in the pathogenesis of dermatitides such as psoriasis. (C) 1998 Elsevier Science Inc.

  DOI：

  10.1016/s0006-2952(97)00464-4
• 作为产物：
  描述：

  N-tert-butoxycarbonyl-S-(4-dimethylamino)benzyl-L-cysteine 在 盐酸 、 苯甲醚 作用下， 反应 1.0h， 生成 (R)-2-Amino-3-(4-dimethylamino-benzylsulfanyl)-propionic acid
  参考文献：
  名称：

  Involvement of Leukotriene B4 in Murine Dermatitis Models

  摘要：

  Leukotriene B-4 (LTB4) is a product of the 5-lipoxygenase pathway of arachidonic acid (AA) metabolism. LTB4 is a potent chemotactic factor for neutrophils and has been postulated to play an important role in a variety of pathological conditions including rheumatoid arthritis, psoriasis, and inflammatory bowel disease. To investigate the role of LTB4 in dermatitis, we used S-(4-dimethylaminobenzyl)-N-[(2S) -mercapto-2-methylpropionyl]-L-cysteine (SA6541), a potent leukotriene A(4) (LTA(4)) hydrolase inhibitor. SA6541 inhibited LTB4 production with an IC50 value of 270 nM in vitro. 5-Hydroperoxyeicosatetraenoic acid (5-HPETE) or AA injection induced LTB4 production and neutrophil influx in mouse ear. SA6541 inhibited 5-HPETE- and AA-induced LTB4 production and neutrophil influx in mouse ear when administered orally at a dose of 50 mg/kg. SA6541 also inhibited 5-HPETE induced prostaglandin E-2 (PGE(2)) production, probably by an indirect effect through the inhibition of LTB4 production. These results suggest that LTB4 map be important in the pathogenesis of dermatitides such as psoriasis. (C) 1998 Elsevier Science Inc.

  DOI：

  10.1016/s0006-2952(97)00464-4

文献信息

• US3976781A
  申请人：——

  公开号：US3976781A

  公开（公告）日：1976-08-24
• Involvement of Leukotriene B4 in Murine Dermatitis Models
  作者：Fumio Tsuji、Yurika Miyake、Masato Horiuchi、Shiro Mita

  DOI：10.1016/s0006-2952(97)00464-4

  日期：1998.2

  Leukotriene B-4 (LTB4) is a product of the 5-lipoxygenase pathway of arachidonic acid (AA) metabolism. LTB4 is a potent chemotactic factor for neutrophils and has been postulated to play an important role in a variety of pathological conditions including rheumatoid arthritis, psoriasis, and inflammatory bowel disease. To investigate the role of LTB4 in dermatitis, we used S-(4-dimethylaminobenzyl)-N-[(2S) -mercapto-2-methylpropionyl]-L-cysteine (SA6541), a potent leukotriene A(4) (LTA(4)) hydrolase inhibitor. SA6541 inhibited LTB4 production with an IC50 value of 270 nM in vitro. 5-Hydroperoxyeicosatetraenoic acid (5-HPETE) or AA injection induced LTB4 production and neutrophil influx in mouse ear. SA6541 inhibited 5-HPETE- and AA-induced LTB4 production and neutrophil influx in mouse ear when administered orally at a dose of 50 mg/kg. SA6541 also inhibited 5-HPETE induced prostaglandin E-2 (PGE(2)) production, probably by an indirect effect through the inhibition of LTB4 production. These results suggest that LTB4 map be important in the pathogenesis of dermatitides such as psoriasis. (C) 1998 Elsevier Science Inc.