3-(3-氨基-2,4,6-三碘-苯基)丙酸 | 1206-91-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: 3-(3-氨基-2,4,6-三碘-苯基)丙酸
• 英文名称: ω-(3-amino-2,4,6-triiodophenyl)propionic acid
• 英文别名: 3-(3-amino-2,4,6-triiodophenyl)propanoic acid；3-(3-amino-2,4,6-triiodo-phenyl)-propionic acid；3-(3-Amino-2,4,6-trijod-phenyl)-propionsaeure；3-<2.4.6-Triiod-3-amino-phenyl>-propionsaeure；3-(2.4.6-Triiod-3-amino-phenyl)-propionsaeure；Cistobil；Hydrocinnamic acid, 3-amino-2,4,6-triiodo-
• CAS: 1206-91-3
• 化学式: C₉H₈I₃NO₂
• 分子量: 542.882
• InChiKey: BVDHMFVGWNGIQE-UHFFFAOYSA-N

物化性质

• 熔点：
  233 °C
• 沸点：
  522.9±50.0 °C(Predicted)
• 密度：
  2.689±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2922499990

制备方法与用途

用途：碘泊酸钙的中间体。

生产方法：通过将间氨基苯丙酸与氯化碘进行反应来制备。

反应信息

• 作为反应物：
  描述：

  3-(3-氨基-2,4,6-三碘-苯基)丙酸 在 4-二甲氨基吡啶 、 硼酸 、 silica gel 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 、 二氯甲烷 、 Petroleum ether 为溶剂， 生成 1-palmitoyl-2-<3-(3-amino-2,4,6-triiodophenyl)propanoyl>-rac-glycerol
  参考文献：
  名称：

  Synthesis and evaluation of iodinated analogs of diacylglycerols as potential probes for protein kinase C

  摘要：

  Analogues of diacylglycerol containing a 3-(3-amino-2,4,6-triiodophenyl)-2-ethylpropanoyl or 3-(3-amino-2,4,6-triiodophenyl)propanoyl group in the 2-position (1a and 1b, respectively) were synthesized and shown to compete with [3H]phorbol dibutyrate [( 3H]PDBu) for binding in a crude rat brain preparation. Phorbol diesters have been shown to bind specifically to protein kinase C and the PDBu receptor has been copurified with protein kinase C activity. The four diastereomers of 1a (1c-f) were synthesized from chiral starting material and studied in the same assay. The affinities for the [3H]PDBu binding site of 1a, 1b, and two isomers of 1a with naturally occurring L configuration were comparable to that of 1-oleoyl-2-acetyl-rac-glycerol (OAG), but the D isomers of 1a were essentially inactive. The chirality of the side chain did not influence the binding affinity. Activation of protein kinase C by 1a, 1c, and 1e demonstrated the same stereochemical requirements, but none were as active as OAG. For the 1,3-isomers 2, 2a, and 2b, the competitive binding studies gave different results. The racemic mixture and the D isomer, 2b, were able to compete for binding, but the L isomer, 2a, did not compete. These studies demonstrate that diacylglycerol binding to and activation of protein kinase C is stereospecific for the glycerol backbone, but not the side chain. Furthermore, the D-1,3-isomer must exist in a conformation such that the acyl and hydroxyl oxygens assume a spatial relationship similar to that in the L-1,2-isomers.

  DOI：

  10.1021/jm00123a024
• 作为产物：
  描述：

  3-氨基苯丙酸 在 盐酸 、 一氯化碘 作用下， 以 水 为溶剂， 反应 3.0h， 以64%的产率得到3-(3-氨基-2,4,6-三碘-苯基)丙酸
  参考文献：
  名称：

  潜在的肿瘤或器官影像检查剂。26.聚碘化的2-取代的三酰基甘油作为肝造影剂。

  摘要：

  合成了一系列ω-（3-氨基-2,4,6-三碘苯基）链烷酸和相应的1,3-二棕榈酰甘油2- [ω-（3-氨基-2,4,6-三碘苯基）链烷酸酯] ，用碘125放射性碘标记，并评估其选择性定位在肝脏中作为肝成像剂的潜在能力。在静脉内给予大鼠5分钟后，酸类似物1d和1e在肝脏中的放射性水平较高（注射剂量为45％和49％）。这些酸显示出与血浆白蛋白结合的明显倾向。相反，三酰基甘油类似物10a和10c并未立即与血浆白蛋白结合，而是迅速与血浆脂蛋白结合，并且显示出与游离酸1a和1c不同的组织分布曲线。尽管长链三酰基甘油类似物10d和10e分别在5分钟和30分钟时表现出一定的肝脏蓄积能力，但血浆分析显示体内酯发生了显着水解。因此，似乎在给药10d和10e之后的肝脏放射性是由于摄取了游离酸而不是完整的三酰基甘油。另一方面，三酰基甘油类似物10a和10c被完整摄取，并在30分钟时显示出肝累积量为给药剂量的25％和35％。

  DOI：

  10.1021/jm00159a019

文献信息

• Polyiodinated Triglyceride Analogs as Potential Computed Tomography Imaging Agents for the Liver
  作者：Jamey P. Weichert、Marc A. Longino、Douglas A. Bakan、Michael G. Spigarelli、Tso-sheng Chou、Susan W. Schwendner、Raymond E. Counsell

  DOI：10.1021/jm00004a010

  日期：1995.2

  A series of glyceryl 2-oleoyl 1,3-bis[omega-(3-amino-2,4,6-triiodophenyl]) alkanoates was synthesized, radioiodinated with iodine-125, emulsified, and evaluated for their ability to selectively localize in the liver for potential use as hepatographic agents in computed tomography. All seven analogs displayed rapid liver uptake wherein between 65 and 78% of the injected dose accumulated in the liver by 30 min. Liver values ranged from 46 to 93% 3 h after injection which corresponded to liver to blood ratios ranging from 21 to 450. Moreover, subsequent elimination of radioactivity from the liver was nearly linear with respect to alkyl chain length. Analogs with longer alkyl chain length were eliminated from the liver more rapidly than their shorter chain counterparts. Because of their biochemical similarities to naturally occurring triglycerides, these novel analogs may prove useful not only for high-resolution anatomic imaging of focal liver lesions, but also for evaluating a variety of diffuse diseases known to affect hepatic function and biochemistry.
• Potential tumor- or organ-imaging agents. 27. Polyiodinated 1,3-disubstituted and 1,2,3-trisubstituted triacylglycerols
  作者：Jamey P. Weichert、Michael P. Groziak、Marc A. Longino、Susan W. Schwendner、Raymond E. Counsell

  DOI：10.1021/jm00162a007

  日期：1986.12

  A series of glyceryl 1,3-bis- and 1,2,3-tris[omega-(3-amino-2,4,6-triiodophenyl)alkanoates] were synthesized, radioiodinated with iodine-125, and evaluated for their ability to selectively localize in the liver for potential use as hepatographic imaging agents. Of the nine target compounds synthesized and evaluated in rats, glyceryl 1,2,3-tris[3-(3-amino-2,4,6-triiodophenyl)propionate] (5b) displayed rapid and sustained liver specificity. This agent was found to accumulate in the liver in concentrations of 60, 75, and 86% of the administered dose at 5 min, 30 min, and 24 h, respectively. Moreover, the 24-h liver-to-blood ratio of 235 justifies further studies in higher animal species.
• Priewe,H.; Poljak,A., Chemische Berichte, 1960, vol. 93, p. 2347 - 2352
  作者：Priewe,H.、Poljak,A.

  DOI：——

  日期：——
• CASSEBAUM; DIERBACH, Pharmazie, 1961, vol. 16, p. 389 - 395
  作者：CASSEBAUM、DIERBACH

  DOI：——

  日期：——
• ARCHER; HOPPE; LEWIS, Journal of the American Pharmaceutical Association (1961), 1951, vol. 40, # 12, p. 617 - 619
  作者：ARCHER、HOPPE、LEWIS

  DOI：——

  日期：——