5-Butyl-2-ethynylpyridine | 136723-73-4

• 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
• 英文名称: 5-Butyl-2-ethynylpyridine
• CAS: 136723-73-4
• 化学式: C₁₁H₁₃N
• 分子量: 159.231
• InChiKey: NDKRTEMDQLHSFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-Butyl-2-ethynylpyridine 在 copper(l) iodide 、 四(三苯基膦)钯 氢氧化钾 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 6-(5-butylpyridin-2-yl)-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]furo[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  Synthesis and Antiviral Evaluation of 6-(Alkyl-heteroaryl)furo[2,3-d]pyrimidin-2(3H)-one Nucleosides and Analogues with Ethynyl, Ethenyl, and Ethyl Spacers at C6 of the Furopyrimidine Core

  摘要：

  Sonogashira coupling strategies were employed to synthesize new furo[2,3-d]pyrimidin-2(3H)-one (FuPyrm) 2'-deoxynucleoside analogues. Partial or complete reduction of ethyne-linked compounds afforded ethenyl-and ethyl-linked derivatives. Levels of inhibition of varicella-zoster virus (VZV), human cytomegalovirus (HCMV), a broad range of other DNA and RNA viruses, and several cancer cell lines were evaluated in cell cultures. The anti-VZV potency decreased with increasing rigidity of the side chain at C6 of the FuPyrm ring in the order dec-1-yn-1-yl < dec-1-en-1-yl < decan-1-yl. In contrast, compounds with a rigid ethynyl spacer between C6 of the FuPyrm ring and a 4-alkylphenyl moiety were more potent inhibitors of VZV than the corresponding derivatives with an ethyl spacer. Replacement of the phenyl moiety in 6-(4-alkylphenyl) derivatives with a pyridine ring (in either regioisomeric orientation) gave analogues with increased solubility in methanol but reduced anti-VZV potency, and replacement with a pyrimidine ring reduced the anti-VZV activity even further. The pyridine-ring-containing analogues were similar to 20-fold more potent inhibitors of VZV than acyclovir but were similar to 6-fold less potent than BVDU and similar to 60-fold weaker than the most active 6-(4-pentylphenyl) -substituted prototype.

  DOI：

  10.1021/jm070210n
• 作为产物：
  描述：

  3-溴吡啶 在 copper(l) iodide 、 四(三苯基膦)钯 正丁基锂 、 三乙胺 、 copper(I) bromide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 5-Butyl-2-ethynylpyridine
  参考文献：
  名称：

  Synthesis and Antiviral Evaluation of 6-(Alkyl-heteroaryl)furo[2,3-d]pyrimidin-2(3H)-one Nucleosides and Analogues with Ethynyl, Ethenyl, and Ethyl Spacers at C6 of the Furopyrimidine Core

  摘要：

  Sonogashira coupling strategies were employed to synthesize new furo[2,3-d]pyrimidin-2(3H)-one (FuPyrm) 2'-deoxynucleoside analogues. Partial or complete reduction of ethyne-linked compounds afforded ethenyl-and ethyl-linked derivatives. Levels of inhibition of varicella-zoster virus (VZV), human cytomegalovirus (HCMV), a broad range of other DNA and RNA viruses, and several cancer cell lines were evaluated in cell cultures. The anti-VZV potency decreased with increasing rigidity of the side chain at C6 of the FuPyrm ring in the order dec-1-yn-1-yl < dec-1-en-1-yl < decan-1-yl. In contrast, compounds with a rigid ethynyl spacer between C6 of the FuPyrm ring and a 4-alkylphenyl moiety were more potent inhibitors of VZV than the corresponding derivatives with an ethyl spacer. Replacement of the phenyl moiety in 6-(4-alkylphenyl) derivatives with a pyridine ring (in either regioisomeric orientation) gave analogues with increased solubility in methanol but reduced anti-VZV potency, and replacement with a pyrimidine ring reduced the anti-VZV activity even further. The pyridine-ring-containing analogues were similar to 20-fold more potent inhibitors of VZV than acyclovir but were similar to 6-fold less potent than BVDU and similar to 60-fold weaker than the most active 6-(4-pentylphenyl) -substituted prototype.

  DOI：

  10.1021/jm070210n

文献信息

• [EN] FUSED 1,4-DIAZEPINES AS BET PROTEIN DEGRADERS<br/>[FR] 1,4-DIAZÉPINES FUSIONNÉES EN TANT QU'AGENTS DE DÉGRADATION DE PROTÉINES BET
  申请人：UNIV MICHIGAN REGENTS

  公开号：WO2018052949A1

  公开（公告）日：2018-03-22

  The present disclosure provides compounds represented by Formula I: I, and the pharmaceutically acceptable salts, hydrates, and solvates thereof, wherein R1, R2a, R2b, R3, R4, Ar, L, X, Y, and B are as defined as set forth in the specification. The present disclosure also provides compounds of Formula I for use to treat a condition or disorder responsive to degradation of BET bromodomains such as cancer.

  本公开提供由式I表示的化合物：I，及其药用可接受的盐、水合物和溶剂合物，其中R1、R2a、R2b、R3、R4、Ar、L、X、Y和B的定义如规范中所述。本公开还提供用于治疗对BET溴结构域降解敏感的疾病或疾病的式I化合物，如癌症。
• [EN] MONOFUNCTIONAL INTERMEDIATES FOR LIGAND-DEPENDENT TARGET PROTEIN DEGRADATION<br/>[FR] INTERMÉDIAIRES MONOFONCTIONNELS POUR LA DÉGRADATION D'UNE PROTÉINE CIBLE DÉPENDANTE DU LIGAND
  申请人：UNIV MICHIGAN REGENTS

  公开号：WO2017176958A1

  公开（公告）日：2017-10-12

  The present disclosure provides compounds represented by Formula I: and the salts or solvates thereof, wherein X, L, Y, and B are as defined in the specification. Compounds having Formula I are immunomodulators and/or monofunctional synthetic intermediates that can be used to prepare small-molecule drug conjugates.

  本公开提供了由式I表示的化合物及其盐或溶剂合物，其中X、L、Y和B如规范中所定义。具有式I的化合物是免疫调节剂和/或可用于制备小分子药物共轭物的单功能合成中间体。
• [EN] ALKYNYL INDAZOLE DERIVATIVE AND USE THEREOF<br/>[FR] DÉRIVÉ ALCYNYLIQUE D'INDAZOLE ET SON UTILISATION<br/>[JA] アルキニルインダゾール誘導体及びその用途
  申请人：SENJU PHARMA CO

  公开号：WO2015152117A1

  公开（公告）日：2015-10-08

  　本発明は、ＶＥＧＦ受容体チロシンキナーゼ阻害活性を有し、例えば加齢性黄斑変性症等の血管新生又は浮腫を伴う疾患の治療剤として有用な新規化合物を提供することを主な課題とする。　本発明として、例えば、下記一般式（Ｉ）で表されるアルキニルインダゾール誘導体、又はその医薬上許容される塩、及びこれらを含む医薬を挙げることができる。（式中、各記号は明細書に記載の通りである。）　上記アルキニルインダゾール誘導体等は、例えば、点眼剤、注射剤等の液剤の形態で使用することができるものである。