1-[(Dimethoxyphosphono)methylamino]cyclooctanecarboxylicacid | 1042937-15-4

• 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: 1-[(Dimethoxyphosphono)methylamino]cyclooctanecarboxylicacid
• 英文别名: 1-(dimethoxyphosphorylmethylamino)cyclooctane-1-carboxylic acid
• CAS: 1042937-15-4
• 化学式: C₁₂H₂₄NO₅P
• 分子量: 293.3
• InChiKey: FLYLVCFFCBHTRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[(Dimethoxyphosphono)methylamino]cyclooctanecarboxylicacid 、 L-丙氨酸 、 L-苯丙氨酸 、 FMOC-O-叔丁基-L-丝氨酸 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 、 Fmoc-O-叔丁基-L-苏氨酸 、 聚甘氨酸 、 Fmoc-Pbf-L-精氨酸 在 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and biological activity of new series of N-modified analogues of the N/OFQ(1–13)NH2 with aminophosphonate moiety

  摘要：

  New series of N-modified analogues of the N/OFQ(1-13)NH2 with aminophosphonate moiety have been synthesized and investigated for biological activity. These peptides were prepared by solid-phase peptide synthesis-Fmoc-strategy. The N/OFQ(1-13)NH2 analogues were tested for agonistic activity in vitro on electrically stimulated rat vas deferens smooth-muscle preparations isolated from Wistar albino rats. Our study has shown that the selectivity of the peptides containing 1-[(methoxyphosphono)methylamino]cycloalkanecarboxylic acids to the N-side of Phe is not changed-they remain selective agonists of NOP receptors. The derivative with the largest ring (NOC-6) demonstrated efficacy similar to that of N/OFQ(1-13)NH2, but in a 10-fold higher concentration. The agonistic activity of newly synthesized N-modified analogues of N/OFQ(1-13)NH2 with aminophosphonate moiety was investigated for the first time.

  DOI：

  10.1007/s00726-011-1177-7
• 作为产物：
  描述：

  聚合甲醛 、 1-氨基-1-环辛烷羧酸 、 亚磷酸二甲酯 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以54.8%的产率得到1-[(Dimethoxyphosphono)methylamino]cyclooctanecarboxylicacid
  参考文献：
  名称：

  Novel N-(phosphonomethyl) glycine derivatives: Design, characterization and biological activity

  摘要：

  A series of C alpha,alpha-disubstituted cyclic derivatives of N-(phosphonomethyl) glycine have been synthesized and characterized. They exhibited moderate clastogenicity, low antiproliferative activity on mice bone marrow cells and well expressed cytotoxicity against human tumor cell lines. The 8- and 12-membered cyclic analogs proved superior to the remaining compounds and were found to trigger apoptotic cell death in DOHH-2 cells. The latter compound caused 50% inhibition of the viability of hemobastose-derived cell lines at concentrations ranging from 20 to 67 mu M. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.08.010

文献信息

• Novel N-(phosphonomethyl) glycine derivatives: Design, characterization and biological activity
  作者：Emilia D. Naydenova、Petar T. Todorov、Margarita N. Topashka-Ancheva、Georgi Ts. Momekov、Tsvetelina Z. Yordanova、Spiro M. Konstantinov、Kolio D. Troev

  DOI：10.1016/j.ejmech.2007.08.010

  日期：2008.6

  A series of C alpha,alpha-disubstituted cyclic derivatives of N-(phosphonomethyl) glycine have been synthesized and characterized. They exhibited moderate clastogenicity, low antiproliferative activity on mice bone marrow cells and well expressed cytotoxicity against human tumor cell lines. The 8- and 12-membered cyclic analogs proved superior to the remaining compounds and were found to trigger apoptotic cell death in DOHH-2 cells. The latter compound caused 50% inhibition of the viability of hemobastose-derived cell lines at concentrations ranging from 20 to 67 mu M. (c) 2007 Elsevier Masson SAS. All rights reserved.
• Synthesis and biological activity of new series of N-modified analogues of the N/OFQ(1–13)NH2 with aminophosphonate moiety
  作者：Petar T. Todorov、Polina I. Mateeva、Rositza N. Zamfirova、Nikola D. Pavlov、Emilia D. Naydenova

  DOI：10.1007/s00726-011-1177-7

  日期：2012.9

  New series of N-modified analogues of the N/OFQ(1-13)NH2 with aminophosphonate moiety have been synthesized and investigated for biological activity. These peptides were prepared by solid-phase peptide synthesis-Fmoc-strategy. The N/OFQ(1-13)NH2 analogues were tested for agonistic activity in vitro on electrically stimulated rat vas deferens smooth-muscle preparations isolated from Wistar albino rats. Our study has shown that the selectivity of the peptides containing 1-[(methoxyphosphono)methylamino]cycloalkanecarboxylic acids to the N-side of Phe is not changed-they remain selective agonists of NOP receptors. The derivative with the largest ring (NOC-6) demonstrated efficacy similar to that of N/OFQ(1-13)NH2, but in a 10-fold higher concentration. The agonistic activity of newly synthesized N-modified analogues of N/OFQ(1-13)NH2 with aminophosphonate moiety was investigated for the first time.