m-fluorophenethyl iodine | 467223-91-2

• 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: m-fluorophenethyl iodine
• 英文别名: 1-fluoro-3-(2-iodoethyl)benzene；2-(3-Fluorophenyl)ethyl iodide
• CAS: 467223-91-2
• 化学式: C₈H₈FI
• 分子量: 250.054
• InChiKey: VEQYTWJAEXPABV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  m-fluorophenethyl iodine 在 偶氮二异丁腈 、 三正丁基氢锡 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 24.0h， 生成 (+)-octahydro-3,6α-dimethyl-3,12-epoxy-9β-(3'-(m-fluorophenyl)propyl)-12H-pyrano[4,3j]-1,2-benzodioxepin-10(3H)-one
  参考文献：
  名称：

  Structure−Activity Relationships of the Antimalarial Agent Artemisinin. 7. Direct Modification of (+)-Artemisinin and In Vivo Antimalarial Screening of New, Potential Preclinical Antimalarial Candidates

  摘要：

  On the basis of earlier reported quantitative structure-activity relationship studies, a series of 9beta-16-(arylalkyl)-10-deoxoartemisinins were proposed for synthesis. Several of the new compounds 7 and 10-14 were synthesized, employing the key synthetic intermediate 23. In a second approach, the natural product (+)-artemisinic acid was utilized as an acceptor for conjugate addition, and the resultant homologated acids were subjected to singlet oxygenation and acid treatment to provide artemisinin analogues. Under a new approach, we developed A one step reaction for the interconversion of artemisinin 1 into artemisitene 22 that did not employ selenium-based reagents and found that 2-arylethyliodides would undergo facile radical-induced conjugate addition to the exomethylene lactone of 22 in good yield. The lactone carbonyls, were removed sequentially by diisobutylaluminum hydride reduction followed directly by a second reduction (BF3-etherate/Et3SiH) to afford the desired corresponding pyrans. Six additional halogen-substituted aromatic side chains were installed via 22 furnishing the bioassay candidates 15-20. The analogues were examined for in vitro antimalarial activity in the W-2 and D-6 clones of Plasmodium falciparum and were additionally tested. in vivo in Plasmodium berghei- and/or Plasmodium yoelii-infected mice. Several of the compounds emerged as highly potent orally active candidates without obvious toxicity, Of these, two were chosen for pharmacokinetic evaluation, 14 and 17.

  DOI：

  10.1021/jm020142z
• 作为产物：
  描述：

  3-氟苯乙酸 在 吡啶 、 lithium aluminium tetrahydride 、 氯化亚砜 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 14.5h， 生成 m-fluorophenethyl iodine
  参考文献：
  名称：

  3,4-二氢-1 H-螺（萘-2,2'-哌啶）-1-酮作为钾竞争性酸阻滞剂的发现，合成及构效关系

  摘要：

  为了发现一种比现有质子泵抑制剂更有效的胃分泌药，新型3,4-二氢-1 H-螺（萘-2,2'-哌啶）-1-酮衍生物可能占据两个重要的位置基于对接模型设计了H +，K + -ATPase的亲脂性口袋（称为LP-1和LP-2），它可以与K +-结合位点牢固结合。在合成的化合物中，化合物4d在大鼠中显示出强大的H +，K + -ATPase抑制活性和高胃浓度，从而对组胺刺激的大鼠胃酸分泌产生有效的抑制作用。此外，4d对大鼠的组胺刺激的胃酸分泌具有显着的抑制作用，给药后起效迅速，作用持续时间适中。这些发现可能会导致对钾竞争性酸阻滞剂药物设计的新见解。

  DOI：

  10.1016/j.bmc.2017.05.012

文献信息

• [EN] ARTEMISININ-BASED PEROXIDE COMPOUNDS AS BROAD SPECTRUM ANTI-INFECTIVE AGENTS<br/>[FR] COMPOSES DE PEROXYDE A BASE D'ARTEMISININE TENANT LIEU D'AGENTS ANTI-INFECTIEUX A LARGE SPECTRE
  申请人：UNIV MISSISSIPI

  公开号：WO2003095444A1

  公开（公告）日：2003-11-20

  Described herein is the synthesis, bioassay results and utility of new C-9 and C-10 substituted artemisinin derivatives with easily functionalizable groups attached to the artemisinin skeleton through carbon chain or heteroatoms. Described also is the demonstration of this class of compounds for their broad-spectrum anti-parasitic activity. Certain of these analogs possess noticeable cytotoxicity deliberately focused on treatment of cancerous diseases.

  本文描述了合成、生物测定结果以及新的C-9和C-10取代青蒿素衍生物的用途，这些衍生物具有易于功能化的基团，通过碳链或杂原子连接到青蒿素骨架上。同时还展示了这类化合物在广谱抗寄生虫活性方面的表现。其中一些类似物具有明显的细胞毒性，专门用于治疗癌症性疾病。
• Enantioselective Polyene Cyclization via Organo-SOMO Catalysis
  作者：Sebastian Rendler、David W. C. MacMillan

  DOI：10.1021/ja100185p

  日期：2010.4.14

  The first organocatalytic enantioselective radical polycyclization has been accomplished using singly occupied molecular orbital (SOMO) catalysis. The presented strategy relies on a selective single-electron oxidation of chiral enamines formed by condensation of polyenals with an imidazolidinone catalyst employing a suitable copper(II) oxidant. The reaction proceeds under mildly acidic conditions at

  第一个有机催化对映选择性自由基多环化是使用单占据分子轨道（SOMO）催化完成的。该策略依赖于多烯醛与咪唑烷酮催化剂、使用合适的铜(II)氧化剂缩合形成的手性烯胺的选择性单电子氧化。该反应在室温弱酸性条件下进行，并显示出与一系列贫电子和富电子官能团的相容性。通过自由基芳基化终止，随后进行氧化和重新芳构化，得到一系列多环醛（12个实例，54-77％产率，85-93％ee）。描述了在单个催化剂控制的级联中最多六个新碳环的对映选择性形成。一系列实验结果表明了基于自由基的级联机制的证据。
• [EN] INHIBITORS OF D-AMINO ACID OXIDASE<br/>[FR] INHIBITEURS D'ACIDE AMINÉ D OXYDASE
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2014025993A1

  公开（公告）日：2014-02-13

  D-amino acid oxidase (DAAO) inhibitors and methods of their use, either alone or in combination with D-serine or D-alanine, to facilitate allosteric activation of NMDA receptor-mediated neurotransmission and methods of their use as therapeutic agents for treating a subject afflicted with one or more cognitive-disorders, such as schizophrenia, including subjects suffering from negative symptoms and cognitive impairments, post-traumatic stress disorder (PTSD), or pain, are disclosed.

  抑制D-氨基酸氧化酶（DAAO）及其使用方法，可以单独使用或与D-丝氨酸或D-丙氨酸结合，以促进NMDA受体介导的神经递质的变构激活，并作为治疗剂用于治疗患有一个或多个认知障碍的受试者，如精神分裂症，包括患有消极症状和认知障碍的受试者，创伤后应激障碍（PTSD）或疼痛等。
• Artemisinin-based peroxide compounds as broad spectrum anti-infective agents
  申请人：Avery Mitchell

  公开号：US20050240034A1

  公开（公告）日：2005-10-27

  Described herein is the synthesis, bioassay results and utility of new C- 9 and C- 10 substituted artemisinin derivatives with easily functionalizable groups attached to the artemisinin skeleton through carbon chain or heteroatoms. Described also is the demonstration of this class of compounds for their broad-spectrum anti-parasitic activity. Certain of these analogs possess noticeable cytotoxicity deliberately focused on treatment of cancerous diseases.

  本文介绍了一种新型C-9和C-10取代青蒿素衍生物的合成、生物测定结果和实用性，这些衍生物通过碳链或杂原子与青蒿素骨架连接，具有易于官能团化的基团。同时，本文还展示了这类化合物的广谱抗寄生虫活性。其中某些类似物具有明显的细胞毒性，可用于治疗癌症疾病。
• INHIBITORS OF D-AMINO ACID OXIDASE
  申请人：THE JOHNS HOPKINS UNIVERSITY

  公开号：US20150218156A1

  公开（公告）日：2015-08-06

  D-amino acid oxidase (DAAO) inhibitors and methods of their use, either alone or in combination with D-serine or D-alanine, to facilitate allosteric activation of NMDA receptor-mediated neurotransmission and methods of their use as therapeutic agents for treating a subject afflicted with one or more cognitive-disorders, such as schizophrenia, including subjects suffering from negative symptoms and cognitive impairments, post-traumatic stress disorder (PTSD), or pain, are disclosed.

  本文介绍了D-氨基酸氧化酶（DAAO）抑制剂及其使用方法，无论是单独使用还是与D-丝氨酸或D-丙氨酸结合使用，以促进NMDA受体介导的神经递质的异构激活，并作为治疗剂治疗患有一种或多种认知障碍的受试者，例如精神分裂症，包括患有消极症状和认知障碍的受试者，创伤后应激障碍（PTSD）或疼痛。