5-碘-4-甲氧基嘧啶 | 219915-13-6

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-碘-4-甲氧基嘧啶
• 英文名称: 5-iodo-4-methoxypyrimidine
• CAS: 219915-13-6
• 化学式: C₅H₅IN₂O
• mdl: MFCD16659692
• 分子量: 236.012
• InChiKey: HUCADZJNOMQGEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  5-碘-4-甲氧基嘧啶 在 palladium on activated charcoal bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 生成 4-methoxy-5-(2-phenylethyl)pyrimidine
  参考文献：
  名称：

  Synthesis and Self-Association of 4-Pyrimidinones

  摘要：

  Crystallization of 4-pyrimidinone from CHCl3 produced colorless needles that were shown by X-ray crystallography to consist of cyclic hydrogen-bonded dimers 2 of the 4(3H)-pyrimidinone tautomer 1. Vapor-pressure osmometry established that a simple derivative, 5-(2-phenylethyl)-4(3H)-pyrimidinone (5), self-associates in solution with a value of K-a (220 +/- 110 m(-1) at 26 degrees C in CH2Cl2) close to that measured for 2-pyridinone under similar conditions. These observations suggest that 4-pyrimidinones and 2-pyridinones have similar modes and degrees of association and should be equally suitable for use as sticky functional groups that can be incorporated in complex molecules to make them associate in particular ways. This hypothesis was tested by synthesizing three dipyrimidinones (12, 16, and 21) designed to form strongly hydrogen-bonded dimers and by making a tetrapyrimidinone (26) designed to self-associate and to thereby generate a three-dimensional hydrogen-bonded network. In all cases, however, the compounds proved to have very low solubilities in organic solvents, and crystals suitable for X-ray diffraction could not be obtained despite intensive effort. It is possible that the simultaneous presence of multiple tautomers, all capable of strong intermolecular association? disfavors the sustained growth of single crystalline phases.

  DOI：

  10.1021/jo981285p
• 作为产物：
  描述：

  甲醇 、 4-氯-5-碘嘧啶 在 sodium methylate 作用下， 反应 6.0h， 以92%的产率得到5-碘-4-甲氧基嘧啶
  参考文献：
  名称：

  探讨嘧啶官能团开关对无环柔性聚合物类似物抗病毒活性的影响

  摘要：

  由于它们能够抑制病毒 DNA 或 RNA 复制，核苷类似物几十年来一直被用作有效的抗病毒疗法。然而，核苷类似物的主要限制之一是抗病毒抗性的发展。在这方面，被称为“fleximers”的柔性核苷类似物多年来一直受到关注，因为它们能够检测酶结合位点中的不同氨基酸，从而克服抗病毒耐药性的潜在发展。无环弯曲聚体先前已证明对多种病毒具有抗病毒活性，包括中东呼吸综合征冠状病毒 (MERS-CoV)、埃博拉病毒 (EBOV)，以及最近的黄病毒，如登革热 (DENV) 和黄热病病毒 (YFV)。由于这些有趣的结果，为了分析嘧啶官能团和酰基保护基团对抗病毒活性、细胞毒性和构象的影响，进行了结构活性关系 (SAR) 研究。本文介绍了这些研究的结果。

  DOI：

  10.3390/molecules24173184

文献信息

• [EN] SULFONAMIDE COMPOUNDS USEFUL AS CYP17 INHIBITORS<br/>[FR] COMPOSÉS DE SULFONAMIDE UTILES EN TANT QU'INHIBITEURS DE CYP17
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2012015723A1

  公开（公告）日：2012-02-02

  Disclosed are sulfonamide compounds of Formula (I): or stereoisomers, N-oxides, prodrugs, or pharmaceutically acceptable salts thereof, wherein ring A, R1, R2, R3, R4 and R5 are defined herein. Also disclosed are methods of using such compounds in the treatment of conditions related to CYP17 enzyme, such as cancer, and pharmaceutical compositions comprising such compounds.

  公开的是化合物的磺胺类化合物的结构式（I）：或其立体异构体、N-氧化物、前药或其药学上可接受的盐，其中环A、R1、R2、R3、R4和R5在此处定义。还公开了使用这类化合物治疗与CYP17酶相关的疾病的方法，如癌症，并包括这类化合物的药物组合物。
• SULFONAMIDE COMPOUNDS USEFUL AS CYP17 INHIBITORS
  申请人：Austin Joel Francis

  公开号：US20140148453A1

  公开（公告）日：2014-05-29

  Disclosed are sulfonamide compounds of Formula (I): or stereoisomers, N-oxides, prodrugs, or pharmaceutically acceptable salts thereof, wherein ring A, R 1 , R 2 , R 3 , R 4 and R 5 are defined herein. Also disclosed are methods of using such compounds in the treatment of conditions related to CYP17 enzyme, such as cancer, and pharmaceutical compositions comprising such compounds.

  本发明涉及式(I)的磺酰胺化合物，或其立体异构体、N-氧化物、前药或其药学上可接受的盐，其中环A、R1、R2、R3、R4和R5如本文所定义。同时，本发明还涉及使用这些化合物治疗与CYP17酶有关的疾病，如癌症，以及包含这些化合物的药物组合物的方法。
• Sulfonamide compounds useful as CYP17 inhibitors
  申请人：Austin Joel Francis

  公开号：US08916553B2

  公开（公告）日：2014-12-23

  Disclosed are sulfonamide compounds of Formula (I): or stereoisomers, N-oxides, prodrugs, or pharmaceutically acceptable salts thereof, wherein ring A, R1, R2, R3, R4 and R5 are defined herein. Also disclosed are methods of using such compounds in the treatment of conditions related to CYP17 enzyme, such as cancer, and pharmaceutical compositions comprising such compounds.

  本发明公开了式(I)的磺胺类化合物，或其立体异构体、N-氧化物、前药或药学上可接受的盐，其中环A、R1、R2、R3、R4和R5在此定义。还公开了使用这种化合物治疗与CYP17酶相关的疾病，如癌症的方法，以及包含这种化合物的制药组合物。
• An unusual cleavage of a C–S bond with concurrent S-arylation under palladium–copper catalysis
  作者：Bidisha Nandi、Kausik Das、Nitya G Kundu

  DOI：10.1016/s0040-4039(00)01253-3

  日期：2000.9

  3-[2-(N-p-Toluenesulfonyl)aminophenylthio]prop-1-yne (4) reacted with aryl iodides 5-14 under palladium-copper catalysis to afford (2-arylthio)-p-toluenesulfonanilide (15-23) in moderate to good yields (54-64%) through unusual depropargylation and S-arylation reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Probing the Effects of Pyrimidine Functional Group Switches on Acyclic Fleximer Analogues for Antiviral Activity
  作者：Mary K. Yates、Payel Chatterjee、Mike Flint、Yafet Arefeayne、Damjan Makuc、Janez Plavec、Christina F. Spiropoulou、Katherine L. Seley-Radtke

  DOI：10.3390/molecules24173184

  日期：——

  Due to their ability to inhibit viral DNA or RNA replication, nucleoside analogues have been used for decades as potent antiviral therapeutics. However, one of the major limitations of nucleoside analogues is the development of antiviral resistance. In that regard, flexible nucleoside analogues known as “fleximers” have garnered attention over the years due to their ability to survey different amino

  由于它们能够抑制病毒 DNA 或 RNA 复制，核苷类似物几十年来一直被用作有效的抗病毒疗法。然而，核苷类似物的主要限制之一是抗病毒抗性的发展。在这方面，被称为“fleximers”的柔性核苷类似物多年来一直受到关注，因为它们能够检测酶结合位点中的不同氨基酸，从而克服抗病毒耐药性的潜在发展。无环弯曲聚体先前已证明对多种病毒具有抗病毒活性，包括中东呼吸综合征冠状病毒 (MERS-CoV)、埃博拉病毒 (EBOV)，以及最近的黄病毒，如登革热 (DENV) 和黄热病病毒 (YFV)。由于这些有趣的结果，为了分析嘧啶官能团和酰基保护基团对抗病毒活性、细胞毒性和构象的影响，进行了结构活性关系 (SAR) 研究。本文介绍了这些研究的结果。