2-氟-4-(碘甲基)吡啶 | 215674-15-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-氟-4-(碘甲基)吡啶
• 中文别名: 2-氟-4-碘甲基吡啶
• 英文名称: 2-fluoro-4-(iodomethyl)-pyridine
• 英文别名: 2-Fluoro-4-(iodomethyl)pyridine
• CAS: 215674-15-0
• 化学式: C₆H₅FIN
• 分子量: 237.015
• InChiKey: MHJIGSWCDKTXJN-UHFFFAOYSA-N

物化性质

• 沸点：
  261.5±30.0 °C(Predicted)
• 密度：
  1.942±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5H-茚并[1,2-b]吡啶 、 2-氟-4-(碘甲基)吡啶 在 乙醇 、 sodium hydride 作用下， 生成 5,5-Bis((2-fluoro-4-pyridinyl)methyl)-5H-indeno[1,2-b]pyridine
  参考文献：
  名称：

  2-Fluoro-4-pyridinylmethyl Analogues of Linopirdine as Orally Active Acetylcholine Release-Enhancing Agents with Good Efficacy and Duration of Action

  摘要：

  In an effort to improve the pharmacokinetic and pharmacodynamic properties of the cognition-enhancer linopirdine (DuP 996), a number of core structure analogues were prepared in which the 4-pyridyl pendant group was systematically replaced with 2-fluoro-4-pyridyl. This strategy resulted in the discovery of several compounds with improved activity in acetylcholine (ACh) release-enhancing assays, in vitro and in vivo. The most effective compound resulting from these studies, 10,10-bis[(2-fluoro-4-pyridinyl)methyl]-9(10H)-anthracenone (9), is between 10 and 20 times more potent than linopirdine in increasing extracellular hippocampal ACh levels in the rat with a minimum effective dose of 1 mg/kg. In addition to superior potency, 9 possesses an improved pharmacokinetic profile compared to that of linopirdine. The half-life of 9 (2 h) in rats is 4-fold greater than that of linopirdine (0.5 h), and it showed a g-fold improvement in brain-plasma distribution over linopirdine. On the basis of its pharmacologic, pharmacokinetic, absorption, and distribution properties, 9 (DMP543) has been advanced for clinical evaluation as a potential palliative therapeutic for treatment of Alzheimer's disease.

  DOI：

  10.1021/jm9803424
• 作为产物：
  描述：

  2-fluoro-4-pyridinemethanol, 4-methylbenzenesulfonate 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 2.5h， 以97%的产率得到2-氟-4-(碘甲基)吡啶
  参考文献：
  名称：

  Efficient Pyridinylmethyl Functionalization:  Synthesis of 10,10-Bis[(2-fluoro-4-pyridinyl)methyl]-9(10H)-anthracenone (DMP 543), an Acetylcholine Release Enhancing Agent

  摘要：

  2-Fluoro-4-methylpyridine (3) is efficiently functionalized by chlorination, hydrolysis and methane-sulfonylation into the novel alkylating agent 7. This mesylate is used for the bisalkylation of anthrone under carefully defined conditions to prepare the cognition enhancer drug candidate 1. This process proceeds in up to 37% overall yield and is adaptable for large scale synthesis.

  DOI：

  10.1021/jo9804339

文献信息

• [EN] CHEMOKINE CXCR4 AND CCR5 RECEPTOR MODULATORS AND USED RELATED THERETO<br/>[FR] MODULATEURS DES RÉCEPTEURS CCR5 ET CXCR4 DE LA CHIMIOKINE ET ET LEURS UTILISATIONS
  申请人：UNIV EMORY

  公开号：WO2015175855A1

  公开（公告）日：2015-11-19

  The disclosure relates to chemokine receptor modulators and uses related thereto. In certain embodiments, the disclosure relates to pharmaceutical compositions comprising compounds disclosed herein or pharmaceutically acceptable salts or prodrugs thereof. In certain embodiments, the compositions disclosed herein are used for managing chemokine related conditions, typically prevention or treatment of viral infections such as HIV or for managing cancer.

  本公开涉及趋化因子受体调节剂及其相关用途。在某些实施例中，本公开涉及包括本公开披露的化合物或其药用盐或前药的制药组合物。在某些实施例中，本公开披露的组合物用于管理与趋化因子相关的疾病，通常是预防或治疗病毒感染如HIV或管理癌症。
• SUBSTITUTED PHENETHYLAMINE DERIVATIVES
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：EP1149843A1

  公开（公告）日：2001-10-31

  The present invention has as its object providing substituted phenethylamine derivatives that function as a motilin receptor antagonist and which are useful as medicines. The invention provides compounds of Formula (1): wherein: Cy is a group of Formula (2): an optionally substituted heterocyclic ring, C3-7cycloalkyl or phenyl; R1, R2, R3, R4 and R5 are hydrogen, halogen, hydroxy, amino, trifluoromethyl or nitrile and at least one of R1, R2, R3, R4 and R5 is halogen, trifluoromethyl or nitrile; R6 is hydrogen, optionally substituted straight-chained or branched C1-3alkyl, amino or hydroxy; R7 is hydrogen, optionally substituted straight-chained or branched C1-3alkyl, optionally substituted amino or hydroxy; R8 is hydrogen, methyl or ethyl; R9 is optionally substituted straight-chained or branched C1-6alkyl, optionally substituted straight-chained or branched C2-6alkenyl, optionally substituted straightchained or branched C2-6alkynyl, C3-7cycloalkyl or optionally substituted phenyl; R20 is hydrogen or straight-chained or branched C1- 3alkyl or R9 and R20 may together form C3-7cycloalkyl; R10 is hydrogen or straight-chained or branched C1- 3alkyl; R11 is hydrogen, optionally substituted straight-chained or branched C1-3alkyl, -CO-N(R14)R15, carboxyl or an optionally substituted heterocyclic ring; R12 is hydroxy or -OR16; R13 is hydrogen, straight-chained or branched C1- 6alkyl, straight-chained or branched C2-6alkenyl, straight-chained or branched C2-6alkynyl or a group of Formula (3): R14 and R15, which may be the same or different, are hydrogen, optionally substituted straight-chained or branched C1-4alkyl, C3-7cycloalkyl, straight-chained or branched C1-4alkyloxy, straight-chained or branched C1-4alkylsulfonyl or a heterocyclic ring, or R14 and R15, as -N(R14)R15, form optionally substituted 3- to 7-membered cyclic amine; R16 is straight-chained C1-4alkyl; R17 is hydrogen or methyl; R18 and R19 together form cycloalkyl or C3-7cycloalkenyl ; X is carbonyl or methylene; Y is carbonyl or methylene; provided that    when Cy is 3-indolyl, (i) R11 is an optionally substituted heterocyclic ring; or (ii) R6 is hydrogen, R7 is amino, R8 is methyl, R9 is isopropyl, R20 is hydrogen, R10 is methyl, R11 is carbamoyl, R12 is hydroxy, R13 is tert-butyl, X is carbonyl and Y is carbonyl, and    when Cy is cyclohexyl or phenyl, R11 is an optionally substituted heterocyclic ring; or a hydrate or pharmaceutically acceptable salt thereof.

  本发明的目的是提供具有动情素受体拮抗剂功能并可用作药物的取代苯乙胺衍生物。 本发明提供了式 (1) 的化合物： 其中 Cy是式(2)的基团： 任选取代的杂环、C3-7 环烷基或苯基； R1、R2、R3、R4 和 R5 是氢、卤素、羟基、氨基、三氟甲基或腈，R1、R2、R3、R4 和 R5 中至少有一个是卤素、三氟甲基或腈； R6 是氢、任选取代的直链或支链 C1-3 烷基、氨基或羟基； R7 是氢、任选取代的直链或支链 C1-3 烷基、任选取代的氨基或羟基； R8 是氢、甲基或乙基； R9 是任选取代的直链或支链 C1-6 烷基、任选取代的直链或支链 C2-6 烯基、任选取代的直链或支链 C2-6 烷炔基、C3-7 环烷基或任选取代的苯基； R20 是氢或直链或支链 C1- 3 烷基，或 R9 和 R20 可共同形成 C3-7 环烷基； R10 是氢或直链或支链 C1- 3 烷基； R11 是氢、任选取代的直链或支链 C1-3 烷基、-CO-N(R14)R15、羧基或任选取代的杂环； R12 是羟基或-OR16； R13 是氢、直链或支链 C1-6 烷基、直链或支链 C2-6 烯基、直链或支链 C2-6 烷炔基或式（3）的基团： R14 和 R15（可以相同或不同）是氢、任选取代的直链或支链 C1-4 烷基、C3-7 环烷基、直链或支链 C1-4 烷氧基、直链或支链 C1-4 烷磺酰基或杂环，或 R14 和 R15 作为 -N(R14)R15 形成任选取代的 3 至 7 元环胺； R16 是直链 C1-4 烷基； R17 是氢或甲基； R18 和 R19 共同形成环烷基或 C3-7 环烯基； X 是羰基或亚甲基 Y 是羰基或亚甲基； 条件是 当 Cy 是 3-吲哚基时 (i) R11 是任选取代的杂环；或 (ii) R6 是氢、R7 是氨基、R8 是甲基、R9 是异丙基、R20 是氢、R10 是甲基、R11 是氨基甲酰基、R12 是羟基、R13 是叔丁基、X 是羰基和 Y 是羰基，以及 当环己基或苯基时，R11 是任选取代的杂环； 或其水合物或药学上可接受的盐。
• J. Med. Chem. 1998, 41, 4615-4622
  作者：

  DOI：——

  日期：——
• CRYSTALLINE 10,10-BIS((2-FLUORO-4-PYRIDINYL)METHYL)-9(10H)-ANTHRACENONE AND AN IMPROVED PROCESS FOR PREPARING THE SAME
  申请人：Du Pont Pharmaceuticals Company

  公开号：EP1003722A1

  公开（公告）日：2000-05-31
• US6214847B1
  申请人：——

  公开号：US6214847B1

  公开（公告）日：2001-04-10