Boc-[Glu-Lys]-Tyr-D-Trp-Lys(Z)-OFm | 757967-73-0

• 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: Boc-[Glu-Lys]-Tyr-D-Trp-Lys(Z)-OFm
• CAS: 757967-73-0
• 化学式: C₆₅H₇₄N₈O₁₁
• 分子量: 1143.35
• InChiKey: PMZDWUDCQQTWDT-GAKVQYFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.44
• 重原子数：
  84.0
• 可旋转键数：
  27.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  272.03
• 氢给体数：
  8.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Boc-[Glu-Lys]-Tyr-D-Trp-Lys(Z)-OFm 在 茴香硫醚 、 氢溴酸 、 1,2-乙二硫醇 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 c[(Glu-Lys)-Tyr-D-Trp-Lys]*HCl
  参考文献：
  名称：

  Design and synthesis of novel type somatostatin analogs with antiproliferative activities on A431 tumor cells

  摘要：

  It was reported that the somatostatin analog TT-232, D-Phe-c(Cys-Tyr-D-Trp-Lys-Cys)-Thr-NH2, exhibited a highly potent antitumor activity in vitro and in vivo. Using pyrazinone analogs and aliphatic amino acids instead of the disulfide bond, we prepared novel type somatostatin analogs including the sequence essential for antitumor activities, Tyr-D-Trp-Lys. These analogs exhibited antiproliferative effect on A431 tumor cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.105
• 作为产物：
  描述：

  BOC-Lys(Z)-OFm 在 盐酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 Boc-[Glu-Lys]-Tyr-D-Trp-Lys(Z)-OFm
  参考文献：
  名称：

  Design and synthesis of novel type somatostatin analogs with antiproliferative activities on A431 tumor cells

  摘要：

  It was reported that the somatostatin analog TT-232, D-Phe-c(Cys-Tyr-D-Trp-Lys-Cys)-Thr-NH2, exhibited a highly potent antitumor activity in vitro and in vivo. Using pyrazinone analogs and aliphatic amino acids instead of the disulfide bond, we prepared novel type somatostatin analogs including the sequence essential for antitumor activities, Tyr-D-Trp-Lys. These analogs exhibited antiproliferative effect on A431 tumor cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.105

文献信息

• New cyclic somatostatin analogues containing a pyrazinone ring: Importance of Tyr for antiproliferative activity
  作者：Anna Miyazaki、Yuko Tsuda、Shoji Fukushima、Toshio Yokoi、Tibor Vántus、Gyöngyi Bökönyi、Edit Szabó、Anikó Horváth、György Kéri、Yoshio Okada

  DOI：10.1016/j.bmcl.2008.10.001

  日期：2008.12

  Novel somatostatin analogues containing a pyrazinone ring, compounds 1 and 2, exhibited good antiproliferative activity on A431 tumor cells. To increase antitumor activity and binding affinity on somatostatin receptors (SSTRs), we substituted Tyr in the critical sequence, Tyr-D-Trp-Lys, with more hydrophobic aromatic residue. The substituted compounds dramatically lost antitumor activity, indicating

  含有吡嗪酮环的新型生长抑素类似物（化合物1和2）对A431肿瘤细胞具有良好的抗增殖活性。为了增加对生长抑素受体（SSTRs）的抗肿瘤活性和结合亲和力，我们在关键序列Tyr-D-Trp-Lys中用更疏水的芳香族残基取代了Tyr。取代的化合物极大地丧失了抗肿瘤活性，表明Tyr残基是必需残基。