4-acetamido-N-(2-(diethylamino)ethyl)-5-iodo-2-methoxybenzamide | 947263-66-3

• 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: 4-acetamido-N-(2-(diethylamino)ethyl)-5-iodo-2-methoxybenzamide
• 英文别名: 4-acetamido-N-[2-(diethylamino)ethyl]-5-iodo-2-methoxybenzamide
• CAS: 947263-66-3
• 化学式: C₁₆H₂₄IN₃O₃
• 分子量: 433.289
• InChiKey: LINIANRIXLAKGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-acetamido-N-(2-(diethylamino)ethyl)-5-iodo-2-methoxybenzamide 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 以91%的产率得到4-amino-N-(2-(diethylamino)ethyl)-5-iodo-2-methoxybenzamide
  参考文献：
  名称：

  Synthesis and Evaluation of Novel Radioiodinated Benzamides for Malignant Melanoma

  摘要：

  The imaging potential of a series of [I-123]benzamides was studied in mice bearing B16F0 melanoma tumors. Compound [I-123]25 exhibited tumor uptake > 8 %ID/g at 1 h, while that of [I-123]14d and [I-123]25 reached a maximum of 9-12 %ID/g at 6 h. Standardized uptake values of [I-123]14d were higher than 100 between 24 and 72 h after injection. In haloperidol treated animals, the tumor uptake of [I-123]14d was not significantly different to controls, while significant reduction of [I-123]25 uptake was observed, supporting that [I-123]14d uptake relates to melanin interaction, whereas part of the mechanism of [I-123]25 uptake is related to its sigma(1)-receptor affinity. Benzamides 14d and 25, which display rapid and high tumor uptake, appear to be promising imaging agents for melanoma detection, while 14d, which displays a long lasting and high melanoma/nontarget ratio, is more suitable for evaluation as a potential radiotherapeutic.

  DOI：

  10.1021/jm0701627
• 作为产物：
  描述：

  4-氨基-N-[2-(二乙基氨基)乙基]-2-甲氧基苯甲酰胺 在 三氟乙酸 、 thallium(III) trifluoroacetate 作用下， 以 乙腈 为溶剂， 反应 6.5h， 生成 4-acetamido-N-(2-(diethylamino)ethyl)-5-iodo-2-methoxybenzamide
  参考文献：
  名称：

  具有高黑色素瘤摄取的放射性碘化N-（2-二乙基氨基乙基）苯甲酰胺衍生物：结构亲和力关系，代谢命运和细胞内定位。

  摘要：

  几种放射性碘化的N-（二烷基氨基烷基）苯甲酰胺已用于黑色素瘤转移的平面闪烁显像和单光子发射计算机断层扫描（SPECT）。为了改善黑素瘤摄取和组织选择性，使用带有B16黑素瘤的C57Bl / 6小鼠进行了具有苯基取代基变化的N-（2-二乙基氨基乙基）苯甲酰胺的结构活性研究。化合物2（4-氨基-5-溴-N-（2-二乙基氨基乙基）-3-[（131）I]碘-2-甲氧基苯甲酰胺）和6（4-乙酰氨基-N-（2-二乙基氨基乙基）-5静脉注射后6小时显示-[[（131）I]碘-2-甲氧基苯甲酰胺e），例如，黑素瘤摄取分别为16.6和23.2％ID / g（平均值，n ＝ 3）。摄取量高3-5倍（P <0。01）比文献中已知的苯甲酰胺所观察到的要好，这可能是由于2或6的尿排泄相对较慢所致。相反，缺乏MeO，Ac，AcNH或Br取代基的类似物表现出降低的肿瘤吸收和高尿酸排泄各种苯甲酰胺代谢产物的放射性。B16

  DOI：

  10.1021/jm991079p

文献信息

• Synthesis and Evaluation of Novel Radioiodinated Benzamides for Malignant Melanoma
  作者：Tien Q. Pham、Ivan Greguric、Xiang Liu、Paula Berghofer、Patrice Ballantyne、Janette Chapman、Filomena Mattner、Branko Dikic、Timothy Jackson、Christian Loc'、Andrew Katsifis

  DOI：10.1021/jm0701627

  日期：2007.7.1

  The imaging potential of a series of [I-123]benzamides was studied in mice bearing B16F0 melanoma tumors. Compound [I-123]25 exhibited tumor uptake > 8 %ID/g at 1 h, while that of [I-123]14d and [I-123]25 reached a maximum of 9-12 %ID/g at 6 h. Standardized uptake values of [I-123]14d were higher than 100 between 24 and 72 h after injection. In haloperidol treated animals, the tumor uptake of [I-123]14d was not significantly different to controls, while significant reduction of [I-123]25 uptake was observed, supporting that [I-123]14d uptake relates to melanin interaction, whereas part of the mechanism of [I-123]25 uptake is related to its sigma(1)-receptor affinity. Benzamides 14d and 25, which display rapid and high tumor uptake, appear to be promising imaging agents for melanoma detection, while 14d, which displays a long lasting and high melanoma/nontarget ratio, is more suitable for evaluation as a potential radiotherapeutic.
• Radioiodinated <i>N</i>-(2-Diethylaminoethyl)benzamide Derivatives with High Melanoma Uptake:  Structure−Affinity Relationships, Metabolic Fate, and Intracellular Localization
  作者：Michael Eisenhut、William E. Hull、Ashour Mohammed、Walter Mier、Dorothee Lay、Wilhelm Just、Karin Gorgas、Wolf D. Lehmann、Uwe Haberkorn

  DOI：10.1021/jm991079p

  日期：2000.10.1

  melanoma uptake and tissue selectivity, structure-activity studies for N-(2-diethylaminoethyl)benzamides with variation of phenyl substituents were performed using C57Bl/6 mice bearing B16 melanoma. Compounds 2 (4-amino-5-bromo-N-(2-diethylaminoethyl)-3-[(131)I]iodo-2-methoxybenz amide) and 6 (4-acetamido-N-(2-diethylaminoethyl)-5-[(131)I]iodo-2-methoxybenzamid e) showed at 6 h post iv injection, for example

  几种放射性碘化的N-（二烷基氨基烷基）苯甲酰胺已用于黑色素瘤转移的平面闪烁显像和单光子发射计算机断层扫描（SPECT）。为了改善黑素瘤摄取和组织选择性，使用带有B16黑素瘤的C57Bl / 6小鼠进行了具有苯基取代基变化的N-（2-二乙基氨基乙基）苯甲酰胺的结构活性研究。化合物2（4-氨基-5-溴-N-（2-二乙基氨基乙基）-3-[（131）I]碘-2-甲氧基苯甲酰胺）和6（4-乙酰氨基-N-（2-二乙基氨基乙基）-5静脉注射后6小时显示-[[（131）I]碘-2-甲氧基苯甲酰胺e），例如，黑素瘤摄取分别为16.6和23.2％ID / g（平均值，n ＝ 3）。摄取量高3-5倍（P <0。01）比文献中已知的苯甲酰胺所观察到的要好，这可能是由于2或6的尿排泄相对较慢所致。相反，缺乏MeO，Ac，AcNH或Br取代基的类似物表现出降低的肿瘤吸收和高尿酸排泄各种苯甲酰胺代谢产物的放射性。B16