3-碘苯乙胺 | 93985-45-6

• 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: 3-碘苯乙胺
• 英文名称: 3-iodophenethyl amine
• 英文别名: 2-(3-iodophenyl)ethyl-1-amine；3-Jod-phenaethylamin；2-(3-Iodophenyl)ethan-1-amine；2-(3-iodophenyl)ethanamine
• CAS: 93985-45-6
• 化学式: C₈H₁₀IN
• 分子量: 247.079
• InChiKey: WXEURTUDSSXUDL-UHFFFAOYSA-N

物化性质

• 沸点：
  286℃
• 密度：
  1.669
• 闪点：
  127℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  花生四烯酸 、 3-碘苯乙胺 在 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以926 mg的产率得到3-Iodophenethylarachidonoylamide
  参考文献：
  名称：

  Synthesis, In Vitro and In Vivo Evaluation, and Radiolabeling of Aryl Anandamide Analogues as Candidate Radioligands for In Vivo Imaging of Fatty Acid Amide Hydrolase in the Brain

  摘要：

  Fatty acid amide hydrolyase (FAAH) is one of the main enzymes responsible for terminating the signaling of endocannabinoids in the brain. Imaging FAAH in vivo using PET or SPECT is important to deeper understanding of its role in neuropsychiatric disorders. However, at present, no radioligand is available for mapping the enzyme in vivo. Here, we synthesized 18 aryl analogues of anandamide, FAAH's endogenous substrate, and in vitro evaluated their potential as metabolic trapping tracers. Interaction studies with recombinant FAAH revealed good to very good interaction of the methoxy substituted aryl anandamide analogues 17, 18, 19, and 20 with FAAH and they were identified as competing substrates, Compounds 17 and 18 did not display significant binding to CB1 and CB2 cannabinoid receptors and stand out as potential candidate metabolic trapping tracers. They were successfully labeled with C-11 in good yields and high radiochemical purity and displayed brain uptake in C57BL/6J mice. Radioligands [C-11]-17 and [C-11]-18 merit further investigation in vivo.

  DOI：

  10.1021/jm900324e
• 作为产物：
  描述：

  3-碘苯乙腈 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 3-碘苯乙胺
  参考文献：
  名称：

  Synthesis, In Vitro and In Vivo Evaluation, and Radiolabeling of Aryl Anandamide Analogues as Candidate Radioligands for In Vivo Imaging of Fatty Acid Amide Hydrolase in the Brain

  摘要：

  Fatty acid amide hydrolyase (FAAH) is one of the main enzymes responsible for terminating the signaling of endocannabinoids in the brain. Imaging FAAH in vivo using PET or SPECT is important to deeper understanding of its role in neuropsychiatric disorders. However, at present, no radioligand is available for mapping the enzyme in vivo. Here, we synthesized 18 aryl analogues of anandamide, FAAH's endogenous substrate, and in vitro evaluated their potential as metabolic trapping tracers. Interaction studies with recombinant FAAH revealed good to very good interaction of the methoxy substituted aryl anandamide analogues 17, 18, 19, and 20 with FAAH and they were identified as competing substrates, Compounds 17 and 18 did not display significant binding to CB1 and CB2 cannabinoid receptors and stand out as potential candidate metabolic trapping tracers. They were successfully labeled with C-11 in good yields and high radiochemical purity and displayed brain uptake in C57BL/6J mice. Radioligands [C-11]-17 and [C-11]-18 merit further investigation in vivo.

  DOI：

  10.1021/jm900324e

文献信息

• Construction of Natural-Product-Like Cyclophane-Braced Peptide Macrocycles via sp³ C–H Arylation
  作者：Bo Li、Xinghua Li、Boyang Han、Zhijie Chen、Xuekai Zhang、Gang He、Gong Chen

  DOI：10.1021/jacs.9b04221

  日期：2019.6.12

  structures. Herein, we report a generally applicable method for synthesis of natural-product-like cyclophane-braced peptide macrocycles via Pd-catalyzed intramolecular C(sp3)-H arylation with aryl iodides at the remote γ position of various N-terminal aliphatic amino acid units using a simple picolinamide directing group. Products of high structural and stereochemical complexity were quickly assembled

  环肽为探索小分子和生物制剂之间的生物相关化学空间提供了最重要的平台之一。然而，与小分子的设计和合成相比，化学家对环肽三维结构和性质的微调能力远远落后。对环烷肽天然产物很感兴趣，我们想知道刚性、平面和疏水性环烷基序是否可以为合成具有良好 3D 结构的环肽提供新的设计元素。在此处，我们报告了一种普遍适用的合成天然产物样环芳支撑的肽大环化合物的方法，通过 Pd 催化的分子内 C(sp3)-H 芳基化，在各种 N 端脂肪族氨基酸单元的远程 γ 位置使用芳基碘进行芳基化，使用简单的吡啶酰胺导向基团。通过标准固相肽合成制备的易于获得的肽前体快速组装具有高度结构和立体化学复杂性的产品。许多这些肽大环化合物显示出高度有序的结构，正如 X 射线晶体学所揭示的那样。值得注意的是，带有各种游离极性侧链的未受保护肽底物的 PA 导向 C(sp3)-H 环化反应在水性介质中以高效率和选择性进行。
• Small molecule and macrocyclic pyrazole derived inhibitors of myeloperoxidase (MPO)
  作者：Carol H. Hu、Meriah W. Neissel Valente、O. Scott Halpern、Sutjano Jusuf、Javed A. Khan、Gregory A. Locke、Gerald J. Duke、Xiaoqin Liu、Franck J. Duclos、Ruth R. Wexler、Ellen K. Kick、Joanne M. Smallheer

  DOI：10.1016/j.bmcl.2021.128010

  日期：2021.6

  antimicrobial host-defense, has been implicated in chronic inflammatory diseases such as coronary artery disease. The design and evaluation of MPO inhibitors for the treatment of cardiovascular disease are reported herein. Starting with the MPO and triazolopyridine 3 crystal structure, novel inhibitors were designed incorporating a substituted pyrazole, which allowed for substituents to interact with hydrophobic

  髓过氧化物酶 (MPO) 是抗微生物宿主防御中的一种关键酶，与慢性炎症性疾病（如冠状动脉疾病）有关。本文报道了用于治疗心血管疾病的 MPO 抑制剂的设计和评价。从 MPO 和三唑并吡啶3晶体结构开始，设计了包含取代吡唑的新型抑制剂，这允许取代基与活性位点中的疏水性和亲水性斑块相互作用。对取代吡唑的 SAR 探索导致哌啶17抑制活化中性粒细胞产生 HOCl，IC 50值为 2.4 μM，对甲状腺过氧化物酶 (TPO) 具有选择性。吡唑氮上烷基化化学的优化促进了许多类似物的制备，包括设计用于桥接活性位点的两个疏水区域的大环。寻求多种大环化策略来制备与活性位点最佳结合的类似物，从而产生具有 TPO 选择性的有效大环 MPO 抑制剂，例如化合物30。
• [EN] AGONISTS OF FOLLICLE STIMULATING HORMONE ACTIVITY<br/>[FR] AGONISTE D'ACTIVITE HORMONALE STIMULANT UN FOLLICULE
  申请人：AFFYMAX RES INST

  公开号：WO2002009706A1

  公开（公告）日：2002-02-07

  In one aspect, the present invention provides novel compounds. In addition, the invention provides a FSH receptor agonist, wherein the agonist binds to a FSH receptor having a FSH binding site and, wherein the agonist is noncompetitve with FSH for the FSH binding site. In another aspect, the invention provides methods of using the compounds of the present invention for diverse pharmaceutical applications including, for example, CNS antiischemic agents, agents with antipsychotic or other psychoactive properties, antimicrobial agents and mammalian fertility regulating agent.

  在一个方面，本发明提供了新型化合物。此外，本发明提供了FSH受体激动剂，其中该激动剂结合到具有FSH结合位点的FSH受体上，且该激动剂在FSH结合位点上与FSH非竞争性地结合。在另一个方面，本发明提供了使用本发明化合物进行各种药物应用的方法，包括例如CNS抗缺血剂、具有抗精神病或其他精神活性特性的剂、抗微生物剂和哺乳动物生育调节剂。
• Heteroaryl substituted pyrrolo[2,3-b]pyridines and pyrrolo[2,3-b]pyrimidines as Janus kinase inhibitors
  申请人：Incyte Corporation

  公开号：EP2343298A1

  公开（公告）日：2011-07-13

  The present invention provides heteroaryl substituted pyrrolo[2,3-b]pyridines (I) and heteroaryl substituted pyrrolo[2,3-b]pyrimidines that modulate the activity of Janus kinases and are useful in the treatment of diseases related to activity of Janus kinases including, for example, immune-related diseases, skin disorders, myeloid proliferative disorders, cancer, and other diseases.

  本发明提供了杂芳基取代的吡咯并[2,3-b]吡啶(I)和杂芳基取代的吡咯并[2,3-b]嘧啶，它们能调节 Janus 激酶的活性，可用于治疗与 Janus 激酶活性有关的疾病，例如包括免疫相关疾病、皮肤病、骨髓增生性疾病、癌症和其他疾病。
• [EN] CYCLIC PEPTIDE COMPOUND SIMULATING NATURAL PRODUCT STRUCTURE, AND METHOD FOR PREPARATION THEREOF<br/>[FR] COMPOSÉ PEPTIDIQUE CYCLIQUE SIMULANT UNE STRUCTURE DE PRODUIT NATUREL, ET SON PROCÉDÉ DE PRÉPARATION<br/>[ZH] 一种模拟天然产物结构的环肽化合物及其制备方法
  申请人：UNIV NANKAI

  公开号：WO2020228097A1

  公开（公告）日：2020-11-19

  涉及一种模拟天然产物结构的环肽化合物及其制备方法。制备方法为：式I化合物、二价钯催化剂和银盐在加热、搅拌作用下在溶剂中进行分子内芳基化反应构建环肽，生成式II化合物。所制备的环肽化合物，芳基化位点具有多样性，可扩展到大部分的疏水性氨基酸（N-端与PA相连的氨基酸）的侧链γ-位甲基或者亚甲基进行分子内芳基化反应构建环肽，克服了原有可选择氨基酸种类局限的缺点，有效地构建了新颖的芳环支撑型环肽化合物。这类环肽的芳环支撑结构能够完全整合入环肽分子的骨架当中，形成新颖的类似天然产物的3D结构，为后续进行环肽分子库的构建以及高通量药物筛选提供了非常有利的支撑。