2-[2-(3,5-二甲基-1H-吡唑-1-基)乙胺基]乙酸 | 1043522-43-5

• 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
• 中文名称: 2-[2-(3,5-二甲基-1H-吡唑-1-基)乙胺基]乙酸
• 英文名称: [2-(3,5-dimethylpyrazol-1-yl)ethylamino]acetic acid
• 英文别名: 2-[2-(3,5-dimethyl-1H-pyrazol-1-yl)ethylamino]acetic acid；2-[2-(3,5-Dimethylpyrazol-1-yl)ethylamino]acetic acid；2-[2-(3,5-dimethylpyrazol-1-yl)ethylamino]acetic acid
• CAS: 1043522-43-5
• 化学式: C₉H₁₅N₃O₂
• 分子量: 197.237
• InChiKey: AOZBNGAQTDQAET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  67.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[2-(3,5-二甲基-1H-吡唑-1-基)乙胺基]乙酸 、 N,N-二乙基氯乙胺 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以36%的产率得到2-[(2-(diethylamino)ethyl)(2-(3,5-dimethyl-1H-pyrazol-1-yl)ethyl)amino]acetic acid
  参考文献：
  名称：

  99mTc(I)/Re(I) tricarbonyl complexes for in vivo targeting of melanotic melanoma: Synthesis and biological evaluation

  摘要：

  The Tc-99m (I) tricarbonyl complexes fac-[Tc-99m(kappa(3)-L)(CO)(3)] (Tc1-Tc6) containing N-ethylpyrrolidine and N,N-diethylethylamine groups for melanin binding, were evaluated in vitro and in vivo as radioactive probes for the targeting of melanotic melanoma. Aiming at the modification of their size, topology and lipophilicity, Tc1-Tc6 were obtained based on an S,N,O-donor bifunctional chelator (BFC) derived from cysteamine and on pyridyl- and pyrazolyl-containing N,N,O-donor BFCs. Tc1-Tc6 were chemically identified by HPLC comparison with the Re congeners (Re1-Re6) that were synthesized at the macroscopic level and fully characterized by common analytical techniques. With the exception of Tc5 and Tc6, these Tc-99m complexes are moderately lipophilic, and bind to melanin with moderate to high affinity (23-87%). The cell uptake of Tc1-Tc6, expressed as a percentage of total activity per million cells, spanned between 0.86 and 21.02% for the melanotic B16-F1 cell line and between 0.49% and 13.58% for the amelanotic A375 cell line. In the B16-F1 cell line, Tc1, Tc3 and Tc4 showed moderate cellular uptake values (>10% at 4 h of incubation). In the amelanotic A375 cell line, only Tc4 has shown a moderate cell uptake (>10% at 4 h of incubation), with all the other compounds displaying a relatively poor uptake, i.e. inferior to 5%. Competition studies with haloperidol have shown that the involvement of sigma receptors in cellular uptake and retention is likely to occur for Tc4. Complex Tc1, stabilized with the S,N,O-donor BFC and containing a N,N-diethylethylamine group, presented the most promising biological profile for in vivo targeting of melanoma, showing a moderate tumor uptake of 2.17% ID/g at 1 h p.i in a B16-F1 melanoma-bearing mouse and rather favorable target/non-target ratios with values as high as 16.9 and 5.2 for tumor/muscle and tumor/blood ratios, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.014
• 作为产物：
  描述：

  聚甘氨酸 、 1-(2-溴乙基)-3,5-二甲基吡唑 以 乙醇 、 水 为溶剂， 反应 96.0h， 以56%的产率得到2-[2-(3,5-二甲基-1H-吡唑-1-基)乙胺基]乙酸
  参考文献：
  名称：

  带有喹唑啉衍生物的hen和tech配合物：向EGFR-TK成像的99m Tc生物标志物发展

  摘要：

  这 喹唑啉 衍生品 （3-氯-4-氟苯基）喹唑啉-4,6-二胺（2）和（3-溴苯基）喹唑啉-4,6-二胺（3）使用“ 4 +1”混合配体系统[Tc（NS 3）（CN-R）]和三羰基部分fac- [Tc（CO）3 ] +标记为99m Tc 。在“ 4 +1”方法中，tech（III）由单齿稳定异氰化物带有喹唑啉片段（L 1 1，L 2 2）和四齿三脚架配体 三（2-巯基乙基）胺（NS 3）。在“ 4 +1”方法中，分两步进行99m Tc标记，即络合物[Tc（NS 3）（L 1 1）]（7a）和[Tc（NS 3）（L 2 2））]（8a）的收率约为50-70％。在三羰基方法中，fac- [Tc（CO）3 ] +单元被两个不同的单阴离子固定螯合剂 轴承 喹唑啉 衍生品 （3-氯-4-氟苯基）喹唑啉-4,6-二胺（2）和（3-溴苯基）喹唑啉-4,6-二胺（3）。两个都螯合剂具有一个N 2 O供体原子组，但一个包含一个吡唑基环（L

  DOI：

  10.1039/b802021c

文献信息

• 99mTc(I)/Re(I) tricarbonyl complexes for in vivo targeting of melanotic melanoma: Synthesis and biological evaluation
  作者：Carolina Moura、Lurdes Gano、Filipa Mendes、Paula D. Raposinho、A.M. Abrantes、M.F. Botelho、Isabel Santos、António Paulo

  DOI：10.1016/j.ejmech.2012.02.014

  日期：2012.4

  The Tc-99m (I) tricarbonyl complexes fac-[Tc-99m(kappa(3)-L)(CO)(3)] (Tc1-Tc6) containing N-ethylpyrrolidine and N,N-diethylethylamine groups for melanin binding, were evaluated in vitro and in vivo as radioactive probes for the targeting of melanotic melanoma. Aiming at the modification of their size, topology and lipophilicity, Tc1-Tc6 were obtained based on an S,N,O-donor bifunctional chelator (BFC) derived from cysteamine and on pyridyl- and pyrazolyl-containing N,N,O-donor BFCs. Tc1-Tc6 were chemically identified by HPLC comparison with the Re congeners (Re1-Re6) that were synthesized at the macroscopic level and fully characterized by common analytical techniques. With the exception of Tc5 and Tc6, these Tc-99m complexes are moderately lipophilic, and bind to melanin with moderate to high affinity (23-87%). The cell uptake of Tc1-Tc6, expressed as a percentage of total activity per million cells, spanned between 0.86 and 21.02% for the melanotic B16-F1 cell line and between 0.49% and 13.58% for the amelanotic A375 cell line. In the B16-F1 cell line, Tc1, Tc3 and Tc4 showed moderate cellular uptake values (>10% at 4 h of incubation). In the amelanotic A375 cell line, only Tc4 has shown a moderate cell uptake (>10% at 4 h of incubation), with all the other compounds displaying a relatively poor uptake, i.e. inferior to 5%. Competition studies with haloperidol have shown that the involvement of sigma receptors in cellular uptake and retention is likely to occur for Tc4. Complex Tc1, stabilized with the S,N,O-donor BFC and containing a N,N-diethylethylamine group, presented the most promising biological profile for in vivo targeting of melanoma, showing a moderate tumor uptake of 2.17% ID/g at 1 h p.i in a B16-F1 melanoma-bearing mouse and rather favorable target/non-target ratios with values as high as 16.9 and 5.2 for tumor/muscle and tumor/blood ratios, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Rhenium and technetium complexes bearing quinazoline derivatives: progress towards a 99mTc biomarker for EGFR-TK imaging
  作者：Célia Fernandes、Isabel C. Santos、I. Santos、Hans-Jurgen Pietzsch、Jens-Uwe Kunstler、Werner Kraus、Ana Rey、Nikos Margaritis、Athanasia Bourkoula、Aris Chiotellis、Maria Paravatou-Petsotas、Ioannis Pirmettis

  DOI：10.1039/b802021c

  日期：——

  the tricarbonyl approach, the fac-[Tc(CO)3]+ unit is anchored by two different monoanionic chelators bearing the quinazoline derivatives (3-chloro-4-fluorophenyl)quinazoline-4,6-diamine (2) and (3-bromophenyl)quinazoline-4,6-diamine (3). Both chelators have a N2O donor atom set, but one contains a pyrazolyl ring (L55H) and the other contains a pyridine unit (L66H). In both cases the conjugation of

  这 喹唑啉 衍生品 （3-氯-4-氟苯基）喹唑啉-4,6-二胺（2）和（3-溴苯基）喹唑啉-4,6-二胺（3）使用“ 4 +1”混合配体系统[Tc（NS 3）（CN-R）]和三羰基部分fac- [Tc（CO）3 ] +标记为99m Tc 。在“ 4 +1”方法中，tech（III）由单齿稳定异氰化物带有喹唑啉片段（L 1 1，L 2 2）和四齿三脚架配体 三（2-巯基乙基）胺（NS 3）。在“ 4 +1”方法中，分两步进行99m Tc标记，即络合物[Tc（NS 3）（L 1 1）]（7a）和[Tc（NS 3）（L 2 2））]（8a）的收率约为50-70％。在三羰基方法中，fac- [Tc（CO）3 ] +单元被两个不同的单阴离子固定螯合剂 轴承 喹唑啉 衍生品 （3-氯-4-氟苯基）喹唑啉-4,6-二胺（2）和（3-溴苯基）喹唑啉-4,6-二胺（3）。两个都螯合剂具有一个N 2 O供体原子组，但一个包含一个吡唑基环（L