α-N-CBZ-L-alanine-2-amino-5-fluorothioanilide | 228404-46-4

• 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: α-N-CBZ-L-alanine-2-amino-5-fluorothioanilide
• 英文别名: benzyl N-[(2S)-1-(2-amino-5-fluoroanilino)-1-sulfanylidenepropan-2-yl]carbamate
• CAS: 228404-46-4
• 化学式: C₁₇H₁₈FN₃O₂S
• 分子量: 347.413
• InChiKey: ILLDBXPAFFILJO-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  光气 、 α-N-CBZ-L-alanine-2-amino-5-fluorothioanilide 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 以70%的产率得到1-(α-N-CBZ-L-thionoalaninyl)-6-fluorobenzimidazolone
  参考文献：
  名称：

  Thioamides:  Synthesis, Stability, and Immunological Activities of Thioanalogues of Imreg. Preparation of New Thioacylating Agents Using Fluorobenzimidazolone Derivatives

  摘要：

  Imreg (Tyr(1)-Gly(2)-Gly(3)) is a well-known immunostimulant, However, it possesses a short half-life. Stabilized analogues of Imreg were prepared by a regioselective insertion in which peptide bonds at position 1,2 or 2,3 were replaced by thioamide linkages. This was achieved by using new thioacylating agents based on thioacyl-fluoro-N-benzimidazolone. The synthesis and properties of these reagents are described herein. This peptide modification enhanced significantly the half-life of the thioanalogues relative to Imreg in blood. The thioanalogues and Imreg were tested in vitro in T and B cell proliferation assays and for their ability to stimulate cytotoxic T-lymphocytes (CTLs). Only thiotyrosyl glycyl glycine 11 displayed some activity as evidenced by a weak stimulation of CTLs. On the basis of this activity and the increased stability, an in vivo immunological evaluation was undertaken. Immunophenotyping of 11 revealed a significant increase in activated CTL and NK cell populations in the spleen. This expansion was also accompanied by a significant stimulation of NK cells and the B cell proliferative response. Thioanalogues of Imreg were generally nontoxic, as exemplified by 11. The latter is a promising immunostimulant which may be targeted for cancer and viral infections, where CTLs and NK cells play an important role, or as a vaccine adjuvant where stimulation of antibody-producing B cells is important.

  DOI：

  10.1021/jm9900467
• 作为产物：
  描述：

  苄氧羰基-L-丙氨酸 在 tetraphosphorus decasulfide 、 TEA 、 sodium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 α-N-CBZ-L-alanine-2-amino-5-fluorothioanilide
  参考文献：
  名称：

  Thioamides:  Synthesis, Stability, and Immunological Activities of Thioanalogues of Imreg. Preparation of New Thioacylating Agents Using Fluorobenzimidazolone Derivatives

  摘要：

  Imreg (Tyr(1)-Gly(2)-Gly(3)) is a well-known immunostimulant, However, it possesses a short half-life. Stabilized analogues of Imreg were prepared by a regioselective insertion in which peptide bonds at position 1,2 or 2,3 were replaced by thioamide linkages. This was achieved by using new thioacylating agents based on thioacyl-fluoro-N-benzimidazolone. The synthesis and properties of these reagents are described herein. This peptide modification enhanced significantly the half-life of the thioanalogues relative to Imreg in blood. The thioanalogues and Imreg were tested in vitro in T and B cell proliferation assays and for their ability to stimulate cytotoxic T-lymphocytes (CTLs). Only thiotyrosyl glycyl glycine 11 displayed some activity as evidenced by a weak stimulation of CTLs. On the basis of this activity and the increased stability, an in vivo immunological evaluation was undertaken. Immunophenotyping of 11 revealed a significant increase in activated CTL and NK cell populations in the spleen. This expansion was also accompanied by a significant stimulation of NK cells and the B cell proliferative response. Thioanalogues of Imreg were generally nontoxic, as exemplified by 11. The latter is a promising immunostimulant which may be targeted for cancer and viral infections, where CTLs and NK cells play an important role, or as a vaccine adjuvant where stimulation of antibody-producing B cells is important.

  DOI：

  10.1021/jm9900467

文献信息

• Thioamides:  Synthesis, Stability, and Immunological Activities of Thioanalogues of Imreg. Preparation of New Thioacylating Agents Using Fluorobenzimidazolone Derivatives
  作者：Boulos Zacharie、Mouna Lagraoui、Marika Dimarco、Christopher L. Penney、Lyne Gagnon

  DOI：10.1021/jm9900467

  日期：1999.6.1

  Imreg (Tyr(1)-Gly(2)-Gly(3)) is a well-known immunostimulant, However, it possesses a short half-life. Stabilized analogues of Imreg were prepared by a regioselective insertion in which peptide bonds at position 1,2 or 2,3 were replaced by thioamide linkages. This was achieved by using new thioacylating agents based on thioacyl-fluoro-N-benzimidazolone. The synthesis and properties of these reagents are described herein. This peptide modification enhanced significantly the half-life of the thioanalogues relative to Imreg in blood. The thioanalogues and Imreg were tested in vitro in T and B cell proliferation assays and for their ability to stimulate cytotoxic T-lymphocytes (CTLs). Only thiotyrosyl glycyl glycine 11 displayed some activity as evidenced by a weak stimulation of CTLs. On the basis of this activity and the increased stability, an in vivo immunological evaluation was undertaken. Immunophenotyping of 11 revealed a significant increase in activated CTL and NK cell populations in the spleen. This expansion was also accompanied by a significant stimulation of NK cells and the B cell proliferative response. Thioanalogues of Imreg were generally nontoxic, as exemplified by 11. The latter is a promising immunostimulant which may be targeted for cancer and viral infections, where CTLs and NK cells play an important role, or as a vaccine adjuvant where stimulation of antibody-producing B cells is important.