N-(3-碘苯甲酰基)甘氨酸 | 52386-94-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(3-碘苯甲酰基)甘氨酸
• 英文名称: 2-(3-iodobenzamido)acetic acid
• 英文别名: m-iodohippuric acid；N-(3-iodo-benzoyl)-glycine；N-(3-Jod-benzoyl)-glycin；3-Jod-benzaminoessigsaeure；3-Jod-hippursaeure；2-[(3-iodobenzoyl)amino]acetic acid
• CAS: 52386-94-4
• 化学式: C₉H₈INO₃
• mdl: MFCD00461204
• 分子量: 305.072
• InChiKey: JFJVYCLGHWPODH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-(3-碘苯甲酰基)甘氨酸 在 N,N-二异丙基乙胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.0h， 生成 N-[2-[[5-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)pentyl]amino]-2-oxoethyl]-3-iodobenzamide
  参考文献：
  名称：

  Preparation of Asymmetric Urea Derivatives that Target Prostate-Specific Membrane Antigen for SPECT Imaging

  摘要：

  Prostate-specific membrane antigen (PSMA) has been identified as a diagnostic and therapeutic target for prostate cancer. (S)-2-[3-[(R)-1-Carboxy-2-mercaptoethyl]ureido-pentanedioic acid (Cys-CO-Glu) were used to design novel PSMA targeting probes by nucleophilic conjugate addition between cysteine and maleimide based reagents. 3 ([I-123]IGLCE) was synthesized by this strategy and showed high affinity for PSMA. Results of binding inhibition assays of these derivatives suggested the importance of an aromatic group and succinimide moiety for high affinity. [I-123]3 was evaluated in vivo with PSMA positive LNCaP and PSMA negative PC-3 human prostate cancer xenograft bearing mice. [I-125]3 accumulated in LNCaP tumors but not in PC-3 tumors, and the accumulation was inhibited by 2-(phosphonomethyl)pentanedioic acid (2-PMPA). Use of [I-123]3 provided positive images of LNCaP tumors in single photon emission tomography scans. These results warrant further evaluation of [I-123]3 and its derivatives as radiolabeled probes for the diagnosis of prostate cancer.

  DOI：

  10.1021/jm400895s
• 作为产物：
  描述：

  3-碘苯甲酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 lithium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N-(3-碘苯甲酰基)甘氨酸
  参考文献：
  名称：

  具有可代谢连接的放射性碘探针的化学设计，用于系统性淀粉样变性的靶点选择性成像

  摘要：

  介绍 系统性淀粉样变性是一种罕见疾病，由淀粉样原纤维在各器官沉积引起。淀粉样蛋白靶向放射性药物已被开发并应用于外周系统性淀粉样变性的诊断；然而，由于正常器官的高背景信号，尚未实现高对比度成像。为了克服这个问题，我们设计了一种具有可代谢键（酯键）的淀粉样蛋白靶向放射性碘标记探针1，可在正常器官中释放放射性标记的代谢物（间碘马尿酸），并可快速从尿液中排出。 方法 通过将淀粉样蛋白靶向化合物2-(4-(甲基氨基)苯基)苯并[ d ]噻唑-6-醇与间碘马尿酸缀合合成化合物1。[ 125 I] 1使用三丁基锡前体通过碘脱甲烷基化合成。通过给小鼠施用淀粉样蛋白增强因子来制备淀粉样蛋白 A (AA) 淀粉样变性（一种系统性淀粉样变性）的小鼠模型，并用于使用器官切片进行体外放射自显影和体内评估。 结果 得到[ 125 I] 1 ，放射化学收率59%，放射化学纯度95%以上。体外放射自显影研究表明，[ 125

  DOI：

  10.1016/j.bmc.2023.117426

文献信息

• Novello; Miriam; Sherwin, Journal of Biological Chemistry, 1926, vol. 67, p. 557
  作者：Novello、Miriam、Sherwin

  DOI：——

  日期：——
• Johnson; Meade, American Chemical Journal, 1906, vol. 36, p. 300
  作者：Johnson、Meade

  DOI：——

  日期：——
• Griess, Chemische Berichte, 1868, vol. 1, p. 192
  作者：Griess

  DOI：——

  日期：——
• Maleimidoethyl 3-(Tri-n-butylstannyl)hippurate: A Useful Radioiodination Reagent for Protein Radiopharmaceuticals To Enhance Target Selective Radioactivity Localization
  作者：Yasushi Arano、Kouji Wakisaka、Yoshiro Ohmomo、Takashi Uezono、Takahiro Mukai、Hiroshi Motonari、Hiromitsu Shiono、Harumi Sakahara、Junji Konishi

  DOI：10.1021/jm00042a014

  日期：1994.8

  In pursuit of radiolabeled monoclonal antibodies (mAbs) with rapid urinary excretion of radioactivity from nontarget tissues, radioiodinated mAbs releasing a m-iodohippuric acid from the mAbs in nontarget tissues were designed. A novel reagent, maleimidoethyl 3-(tri-n-butylstannyl)hippurate (MIH), was synthesized by reacting N-(hydroxyethyl)maleimide with N-Boc-glycine before coupling with N-succinimidyl 3-(tri-n-butylstannyl)benzoate (ATE). MIH possessed a maleimide group for mAb conjugation and a butylstannyl moiety for high-yield and site-specific radioiodination, and the two functional groups were linked via an ester bond to release m-iodohippuric acid. To investigate the fate of radiolabels after lysosomal proteolysis, hepatic parenchymal cells were used as a model nontarget tissue and I-131-labeled MIH was conjugated with galactosyl-neoglycoalbumin (NGA). Further conjugation of[I-131]MIH with a mAb against osteogenic sarcoma (OST7) after reduction of its disulfide bonds was followed up. In murine biodistribution studies, [I-131]MIH-NGA exhibited rapid accumulation in the liver followed by radioactivity elimination from the liver at a rate that was identical to and faster than those of I-131-labeled NGA via direct iodination ([I-131]NGA) and [I-131]ATE-labeled NGA, respectively. While [I-131]NGA indicated high radioactivity levels in the murine neck, stomach, and blood, such increases in the radioactivity count were not detectable by the administration of either [I-131]MIH-NGA or [I-131]ATE-NGA. At 6 h postinjection of [I-131]MIH-NGA, 80% of the injected radioactivity was recovered in the urine. Analyses of urine samples indicated that m-iodohippuric acid was the sole radiolabeled metabolite. In biodistribution studies using [I-131]MIH-OST7 and [I-131]ATE-OST7, while both I-131-labeled OST7s registered almost identical radioactivity levels in the blood up to 6 h postinjection, the former demonstrated a lower radioactivity level than [I-131]ATE-OST7 in nontarget tissues throughout the experiment. Such chemical and biological characteristics of MIH would enable high target/nontarget ratios in diagnostic and therapeutic nuclear medicine using mAbs and other polypeptides.
• 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.