6-(3-iodobenzamido)hexanoic acid

• 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: 6-(3-iodobenzamido)hexanoic acid
• 英文别名: 6-[(3-iodobenzoyl)amino]hexanoic Acid
• 化学式: C₁₃H₁₆INO₃
• mdl: MFCD03544663
• 分子量: 361.179
• InChiKey: JDYDHGWUYUAFFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  、 6-(3-iodobenzamido)hexanoic acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-iodo-N-[6-[[2-[2-(4-methoxyphenyl)ethylamino]-2-oxoethyl]-[2-oxo-2-(2-phenylethylamino)ethyl]amino]-6-oxohexyl]benzamide
  参考文献：
  名称：

  Convergent Solution-Phase Combinatorial Synthesis with Multiplication of Diversity through Rigid Biaryl and Diarylacetylene Couplings

  摘要：

  The solution-phase synthesis of iminodiacetic acid diamide libraries Linked to aryl iodides and their Pd-catalyzed dimerization are detailed. Mixtures containing 64 980 components are synthesized in only 4 steps from N-BOC-iminodiacetic acid anhydride (1) and 21 readily available starting materials, demonstrating the multiplication of diversity achievable by the convergent assembly of building blocks. Both biaryl formation and sequential Stille couplings with bis(tributylstannyl)acetylene are utilized to dimerize the functionalized iminodiacetic acid diamide precursors resulting in product libraries with two sets of binding groups separated by variable length rigid linkers suitable for probing protein-protein interactions. Deconvolution libraries synthesized alongside the full mixtures allow for identification of active components.

  DOI：

  10.1021/jo990639p
• 作为产物：
  描述：

  3-碘苯甲酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.13h， 生成 6-(3-iodobenzamido)hexanoic acid
  参考文献：
  名称：

  Synthesis and Evaluation of Radioiodinated Acyloxymethyl Ketones as Activity-Based Probes for Cathepsin B

  摘要：

  Dipeptidyl (acyloxy)methyl ketones (AOMKs) were functionalized with different iodine-containing prosthetic groups to generate a library of candidate cathepsin B probes. Compound 23a, (S)-20-[(S)-2-{[(benzyloxy)carbonyl]amino}-3-phenylpropanamido]-1-(4-iodophenyl)-1,14,21-trioxo-5,8,11-trioxa-2,15-diazadocosan-22-yl 2,4,6-trimethylbenzoate, was identified as a potential lead through in vitro screening, having a K-i = 181 +/- 9 nM and demonstrating the ability to effectively label active cathepsin B in vitro. Its less potent analogue 11a, (S)-3-[(S)-2-{[(benzyloxy)carbonyl]amino}-3-phenylpropanamido]-7-[6-(4-iodobenzamido)hexanamido]-2-oxoheptyl 2,4,6-trimethylbenzoate, was also tested as a comparison. Biodistribution studies of the iodine-125-labeled compounds in MDA-MB-231 mouse xenografts exhibited tumor uptake of 0.58% +/- 0.06% injected dose per gram (ID/g) for [I-125]11a and 1.12% +/- 0.08% ID/g for [I-125]23a at 30 min. The tumor-to-blood ratios reached 1.2 for [I-125]23a and 1.6 for [I-125]11a after 23 h. The more hydrophilic [I-125]23a showed an improved clearance profile with a superior tumor-to-muscle ratio of 7.0 compared to 3.4 for [I-125]11a at 23 h. Iodinated AOMK ligands are suitable in vitro probes for cathepsin B and hold promise as a platform to develop molecular imaging probes.

  DOI：

  10.1021/jm501357r

文献信息

• CA-IX SPECIFIC RADIOPHARMACEUTICALS FOR THE TREATMENT AND IMAGING OF CANCER
  申请人：Molecular Insight Pharmaceuticals, Inc.

  公开号：EP2373622A2

  公开（公告）日：2011-10-12
• [EN] CA-IX SPECIFIC RADIOPHARMACEUTICALS FOR THE TREATMENT AND IMAGING OF CANCER<br/>[FR] PRODUITS RADIOPHARMACEUTIQUES SPÉCIFIQUES DE CA-IX POUR LE TRAITEMENT ET L'IMAGERIE DE CANCER
  申请人：MOLECULAR INSIGHT PHARM INC

  公开号：WO2010065906A2

  公开（公告）日：2010-06-10

  A compound that recognizes and binds to the CA-IX protein has Formula I, II, III, or IV. The compounds may include a radioactive element for radioimaging or therapeutic applications. Thus, pharmaceutical compositions may be prepared with one or more of the compounds of Formula (I), (II), (III), or (IV).
• Synthesis and Evaluation of Radioiodinated Acyloxymethyl Ketones as Activity-Based Probes for Cathepsin B
  作者：Patricia E. Edem、Shannon Czorny、John F. Valliant

  DOI：10.1021/jm501357r

  日期：2014.11.26

  Dipeptidyl (acyloxy)methyl ketones (AOMKs) were functionalized with different iodine-containing prosthetic groups to generate a library of candidate cathepsin B probes. Compound 23a, (S)-20-[(S)-2-[(benzyloxy)carbonyl]amino}-3-phenylpropanamido]-1-(4-iodophenyl)-1,14,21-trioxo-5,8,11-trioxa-2,15-diazadocosan-22-yl 2,4,6-trimethylbenzoate, was identified as a potential lead through in vitro screening, having a K-i = 181 +/- 9 nM and demonstrating the ability to effectively label active cathepsin B in vitro. Its less potent analogue 11a, (S)-3-[(S)-2-[(benzyloxy)carbonyl]amino}-3-phenylpropanamido]-7-[6-(4-iodobenzamido)hexanamido]-2-oxoheptyl 2,4,6-trimethylbenzoate, was also tested as a comparison. Biodistribution studies of the iodine-125-labeled compounds in MDA-MB-231 mouse xenografts exhibited tumor uptake of 0.58% +/- 0.06% injected dose per gram (ID/g) for [I-125]11a and 1.12% +/- 0.08% ID/g for [I-125]23a at 30 min. The tumor-to-blood ratios reached 1.2 for [I-125]23a and 1.6 for [I-125]11a after 23 h. The more hydrophilic [I-125]23a showed an improved clearance profile with a superior tumor-to-muscle ratio of 7.0 compared to 3.4 for [I-125]11a at 23 h. Iodinated AOMK ligands are suitable in vitro probes for cathepsin B and hold promise as a platform to develop molecular imaging probes.
• Convergent Solution-Phase Combinatorial Synthesis with Multiplication of Diversity through Rigid Biaryl and Diarylacetylene Couplings
  作者：Dale L. Boger、Weiqin Jiang、Joel Goldberg

  DOI：10.1021/jo990639p

  日期：1999.9.1

  The solution-phase synthesis of iminodiacetic acid diamide libraries Linked to aryl iodides and their Pd-catalyzed dimerization are detailed. Mixtures containing 64 980 components are synthesized in only 4 steps from N-BOC-iminodiacetic acid anhydride (1) and 21 readily available starting materials, demonstrating the multiplication of diversity achievable by the convergent assembly of building blocks. Both biaryl formation and sequential Stille couplings with bis(tributylstannyl)acetylene are utilized to dimerize the functionalized iminodiacetic acid diamide precursors resulting in product libraries with two sets of binding groups separated by variable length rigid linkers suitable for probing protein-protein interactions. Deconvolution libraries synthesized alongside the full mixtures allow for identification of active components.