4-fluoro-3-iodobenzoyl chloride | 1170669-90-5

• 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-fluoro-3-iodobenzoyl chloride
• CAS: 1170669-90-5
• 化学式: C₇H₃ClFIO
• 分子量: 284.456
• InChiKey: CWRFGJSRTDUHSN-UHFFFAOYSA-N

物化性质

• 沸点：
  274.1±25.0 °C(Predicted)
• 密度：
  2.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-fluoro-3-iodobenzoyl chloride 在 三甲基氯硅烷 、 1,2-二溴乙烷 、 三乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 lithium chloride 、 cobalt(II) chloride 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 79.0h， 生成 2,3,5,6-tetrafluorophenyl 4-fluoro-3-[tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)stannyl]benzoate
  参考文献：
  名称：

  Development and Preliminary Evaluation of TFIB, a New Bimodal Prosthetic Group for Bioactive Molecule Labeling

  摘要：

  The new readily available prosthetic group, tetrafluorophenyl 4-fluoro-3-iodobenzoate (TFIB), designed for both molecular imaging and targeted radionuclide therapy purposes was radiolabeled either with fluorine or iodine radionuclides with excellent radiochemical yields and purities. These radiolabeled tags were conjugated to N,N-diethylethylenediamine to give melanin-targeting radiotracers [ (125) I]9 and [ (18) F]9, which were successfully evaluated by PET and gamma scintigraphic imaging in B16F0 pigmented melanoma-bearing C57BL/6J mice. Then, radiolabeled [ (125) I]/[ (18) F]TFIB was used to tag tumor-targeting peptides (i.e., PEG3[c(RGDyK)]2 and NDP-MSH targeting αvβ3 integrin and MC1R receptors, respectively) in mild conditions and with good radiochemical yields (47-83% d.c.) and purities (>99%). The resulting radiolabeled peptides were assessed both in vitro and by PET imaging in animal models.

  DOI：

  10.1021/ml500423v
• 作为产物：
  描述：

  3-氨基-4-氟苯甲酸 在 盐酸 、 草酰氯 、 N,N-二甲基甲酰胺 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 21.0h， 生成 4-fluoro-3-iodobenzoyl chloride
  参考文献：
  名称：

  Development and Preliminary Evaluation of TFIB, a New Bimodal Prosthetic Group for Bioactive Molecule Labeling

  摘要：

  The new readily available prosthetic group, tetrafluorophenyl 4-fluoro-3-iodobenzoate (TFIB), designed for both molecular imaging and targeted radionuclide therapy purposes was radiolabeled either with fluorine or iodine radionuclides with excellent radiochemical yields and purities. These radiolabeled tags were conjugated to N,N-diethylethylenediamine to give melanin-targeting radiotracers [ (125) I]9 and [ (18) F]9, which were successfully evaluated by PET and gamma scintigraphic imaging in B16F0 pigmented melanoma-bearing C57BL/6J mice. Then, radiolabeled [ (125) I]/[ (18) F]TFIB was used to tag tumor-targeting peptides (i.e., PEG3[c(RGDyK)]2 and NDP-MSH targeting αvβ3 integrin and MC1R receptors, respectively) in mild conditions and with good radiochemical yields (47-83% d.c.) and purities (>99%). The resulting radiolabeled peptides were assessed both in vitro and by PET imaging in animal models.

  DOI：

  10.1021/ml500423v

文献信息

• The development of phenylethylene dendrons for blue phosphorescent emitters
  作者：Shih-Chun Lo、Ruth E. Harding、Edward Brightman、Paul L. Burn、Ifor D. W. Samuel

  DOI：10.1039/b820235d

  日期：——

  New high triplet energy dendrons based on 1,2-diphenylethylene with and without 2-ethylhexyloxy surface groups have been developed for deep blue phosphorescent iridium(III) dendrimers. The fac-tris[1-methyl-5-(4-fluoro)phenyl-3-n-propyl-1H-[1,2,4]triazolyl]iridium(III)-cored dendrimers, bearing first generation 1,2-diphenylethylene dendrons on the ligand triazolyl and phenyl rings, were prepared in excellent yields, employing Sonogashira cross-couplings and palladium catalysed hydrogenation as the key synthetic steps. Both dendrimers showed good thermal stability although the flexible nature of the dendrons led to the materials having low glass transition temperatures. Dendrimer 15 (without the surface groups) emitted good blue phosphorescence with a solution photoluminescence quantum yield (PLQY) of 46%, Commission Internationale de l'Eclairage (CIE) co-ordinates of (0.15, 0.14) and photoluminescence peaks at 441 and 468 nm. The solution PLQY was 50% higher than the parent iridium(III) complex showing that the high triplet energy of the diphenylethylene dendrons does not quench the luminescence of the iridium(III) complex core. Dendrimer 34, which has the surface groups, had a film PLQY of 49% and CIE co-ordinates of (0.16, 0.19) with PL peaks at 441 and 469 nm.

  基于1,2-二苯乙烯的新高三重态能量树状聚合物，分别添加和不添加2-乙基己氧基表面基团，已被开发用于深蓝色磷光铱(III)树状聚合物。这些以fac-tris[1-甲基-5-(4-氟)苯基-3-n-丙基-1H-[1,2,4]三唑基]铱(III)为核心的树状聚合物，具有第一代1,2-二苯乙烯树枝在配体三唑基和苯环上，采用Sonogashira交叉偶联和钯催化氢化作为关键合成步骤，获得了优异的产率。这两种树状聚合物虽然展现了良好的热稳定性，但由于树枝的柔性特性，使材料具有较低的玻璃转变温度。树状聚合物15（不带表面基团）发出了良好的蓝色磷光，溶液光致发光量子产率（PLQY）为46%，国际照明委员会（CIE）坐标为(0.15, 0.14)，光致发光峰值分别位于441 nm和468 nm。其溶液PLQY比母体铱(III)复合物高出50%，表明二苯乙烯树状聚合物的高三重态能量并未抑制铱(III)复合物核心的发光。树状聚合物34（带有表面基团）在薄膜中的PLQY为49%，CIE坐标为(0.16, 0.19)，光致发光峰值位于441 nm和469 nm。
• Design and Synthesis of Novel and Selective Phosphodiesterase 2 (PDE2a) Inhibitors for the Treatment of Memory Disorders
  作者：Laurent Gomez、Mark Eben Massari、Troy Vickers、Graeme Freestone、William Vernier、Kiev Ly、Rui Xu、Margaret McCarrick、Tami Marrone、Markus Metz、Yingzhou G. Yan、Zachary W. Yoder、Robert Lemus、Nicola J. Broadbent、Richard Barido、Noelle Warren、Kara Schmelzer、David Neul、Dong Lee、Carsten B. Andersen、Kristen Sebring、Kathleen Aertgeerts、Xianbo Zhou、Ali Tabatabaei、Marco Peters、J. Guy Breitenbucher

  DOI：10.1021/acs.jmedchem.6b01793

  日期：2017.3.9

  5-a]pyrimidine PDE2a inhibitors is reported. The design and improvement of the binding properties of this series was achieved using X-ray crystal structures in conjunction with careful analysis of electronic and structural requirements for the PDE2a enzyme. One of the lead compounds, compound 27 (DNS-8254), was identified as a potent and highly selective PDE2a enzyme inhibitor with favorable rat pharmacokinetic

  报道了一系列有效的和选择性的[1,2,4]三唑[1,5- a ]嘧啶PDE2a抑制剂。使用X射线晶体结构并仔细分析PDE2a酶的电子和结构要求，可以设计和改进该系列的结合性能。一种主要化合物，化合物27（DNS-8254）被确定为一种有效且高选择性的PDE2a酶抑制剂，具有良好的大鼠药代动力学特性。有趣的是，与PDE2a活性位点中存在的Tyr827的氧形成卤素键，促进了化合物27效力的提高。体内化合物27在新型物体识别的大鼠模型中显示出显着的记忆增强作用。综上所述，这些数据表明化合物27可能是探索选择性PDE2a抑制作用的药理学的有用工具。
• HETEROARYL ALKYNE COMPOUND AND USE THEREOF
  申请人：NANJING SANHOME PHARMACEUTICAL CO., LTD.

  公开号：US20150299202A1

  公开（公告）日：2015-10-22

  In the field of pharmaceutical chemistry compounds of general formula I having heteroaryl alkynyl moiety or pharmaceutically acceptable salts, isomers, solvates, crystals or prodrugs thereof, and pharmaceutical compositions including these compounds, as well as uses of these compounds and compositions thereof in the manufacture of a medicament. The compounds have a strong inhibitory effect on BCR-ABL tyrosine kinase and are useful for treating diseases, such as tumors.

  在药物化学领域，具有异杂环炔基团或其药学上可接受的盐、异构体、溶剂化物、晶体或前药的通式I化合物，以及包括这些化合物的药物组合物，以及这些化合物和组合物在制造药物方面的用途。这些化合物对BCR-ABL酪氨酸激酶具有强烈的抑制作用，可用于治疗肿瘤等疾病。
• HETEROARYL ALKYNE COMPOUND AND APPLICATION THEREOF
  申请人：Nanjing Sanhome Pharmaceutical Co., Ltd.

  公开号：EP2927232A1

  公开（公告）日：2015-10-07

  The present invention belongs to the field of pharmaceutical chemistry. Specifically, the invention relates to compounds of general formula I having heteroaryl alkynyl moiety or pharmceutically acceptable salts, isomers, solvates, crystals or prodrugs thereof, and pharmaceutical compositions comprising these compounds, as well as uses of these compounds and compositions thereof in the manufacture of a medicament. The compounds of the present invention have a strong inhibitory effect on BCR-ABL tyrosine kinase and are useful for treating diseases, such as tumors.

  本发明属于药物化学领域。具体而言，本发明涉及具有杂芳基炔基的通式 I 化合物或其药学上可接受的盐、异构体、溶液剂、晶体或原药，以及包含这些化合物的药物组合物，以及这些化合物及其组合物在制造药物中的用途。本发明的化合物对BCR-ABL酪氨酸激酶有很强的抑制作用，可用于治疗肿瘤等疾病。
• Discovery of novel Ponatinib analogues for reducing KDR activity as potent FGFRs inhibitors
  作者：Yang Liu、Xia Peng、Xiaocong Guan、Dong Lu、Yong Xi、Shiyu Jin、Hui Chen、Limin Zeng、Jing Ai、Meiyu Geng、Youhong Hu

  DOI：10.1016/j.ejmech.2016.10.003

  日期：2017.1

  FGF receptors (FGFRs) are tyrosine kinases that are overexpressed in diverse tumors by genetic alterations such as gene amplifications, somatic mutations and translocations. Owing to this characteristic, FGFRs are attractive targets for cancer treatment. It has been demonstrated that most multi-targeted, ATP competitive tyrosine kinase inhibitors are active against FGFRs as well as other kinases. The design of new and more selective inhibitors of FGFRs, which might be reduced off-target and side effects, is a difficult yet significant challenge. The results of the current investigation, show that novel Ponatinib analogues are highly active as FGFR inhibitors and that they possess reduced kinase insert domain receptor (KDR) activities. Observations made in a structure and activity relationship (SAR) investigation led to the development of a promising, orally available lead compound 4, which displays a 50-100 fold in vitro selectivity for inhibition of FGFR1-3 over KDR. In addition, biological evaluation of compound 4 showed that it displays significant antitumor activities in FGFR1-amplificated H1581 and FGFR2amplificated SNU-16 xenograft models. (C) 2016 Elsevier Masson SAS. All rights reserved.