N-1-propargyl-5-chlorouracil | 198827-86-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N-1-propargyl-5-chlorouracil
• 英文别名: 5-chloro-1-(prop-2-ynyl)pyrimidine-2,4(1H,3H)-dione；5-Chloro-1-prop-2-ynyl-pyrimidine-2,4-dione；5-chloro-1-prop-2-ynylpyrimidine-2,4-dione
• CAS: 198827-86-0
• 化学式: C₇H₅ClN₂O₂
• 分子量: 184.582
• InChiKey: NGJBFUBMVJQUGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-1-propargyl-5-chlorouracil 在 氨 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 24.0h， 生成 1-[[1-[(4-hydroxyethoxy)methyl]-1,2,3-triazol-4-yl]methyl]-5-chlorouracil
  参考文献：
  名称：

  SYNTHESIS AND ANTI-HIV ACTIVITY OF NEW MODIFIED 1,2,3-TRIAZOLE ACYCLONUCLEOSIDES

  摘要：

  The synthesis of 1,2,3-triazole acyclonucleosides 7a-h via 1,3-dipolar cycloaddition of N-9/N-1-propargyipurine/pyrimidine 2a-h with azido-pseudo-sugar 4 is described and none of them had anti-HlV activity.

  DOI：

  10.1081/ncn-100108325
• 作为产物：
  描述：

  1-(丙-2-炔-1-基)嘧啶-2,4(1H,3H)-二酮 在 N-氯代丁二酰亚胺 作用下， 以 吡啶 为溶剂， 反应 0.5h， 以92%的产率得到N-1-propargyl-5-chlorouracil
  参考文献：
  名称：

  SYNTHESIS AND ANTI-HIV ACTIVITY OF NEW MODIFIED 1,2,3-TRIAZOLE ACYCLONUCLEOSIDES

  摘要：

  The synthesis of 1,2,3-triazole acyclonucleosides 7a-h via 1,3-dipolar cycloaddition of N-9/N-1-propargyipurine/pyrimidine 2a-h with azido-pseudo-sugar 4 is described and none of them had anti-HlV activity.

  DOI：

  10.1081/ncn-100108325

文献信息

• One-Pot Synthesis of N-Alkyl Purine, Pyrimidine and Azole Derivatives from Alcohols using Ph3P/CCl4: A Rapid Route to Carboacyclic Nucleoside Synthesis
  作者：Mohammad Soltani Rad、Ali Khalafi-Nezhad、Somayeh Behrouz、Zeinab Asrari、Marzieh Behrouz、Zohreh Amini

  DOI：10.1055/s-0029-1216887

  日期：2009.9

  A facile and efficient method for one-pot N-alkylation of nucleobases and azole derivatives from alcohols using triphenylphosphine in carbon tetrachloride is described. In this method, treatment of alcohols with a mixture of triphenylphosphine, carbon tetrachloride, nucleobase or azole derivatives and potassium carbonate in the presence of catalytic amounts of tetra-n-butylammonium iodide (TBAI) in

  描述了一种在三氯化碳中使用三苯基膦对醇进行的核碱基和唑衍生物的一锅N-烷基化的简便有效方法。在这种方法中，在催化量的四正丁基碘化铵（TBAI）存在下，在回流的N，N-二甲基甲酰胺中，用三苯基膦，四氯化碳，核碱基或唑衍生物和碳酸钾的混合物处理醇，得到了相应的N-烷基衍生物，收率高。该方法学对于各种结构多样的伯醇是高效的，并且也可用于含有酸性NH键的其他N-杂环的N-烷基化。 碳环核苷-N-烷基化-核碱基-醇-三苯膦-四氯化碳-碳酸钾
• Efficient and selective catalytic N-Alkylation of pyrimidine by ammonium Sulfate@Hydro-thermal carbone under eco-friendly conditions
  作者：SOUMIA BELKHARCHACH、HANA IGHACHANE、ABDESSADEK LACHGAR、MUSTAPHA AIT ALI、HASSAN B LAZREK

  DOI：10.1007/s12039-020-01776-3

  日期：2020.12

  An efficient and inexpensive method for the N-alkylation of pyrimidines using ammonium sulfate coated Hydro-Thermal-Carbone (HTC) (AS@HTC) as reused heterogeneous catalyst was developed. The catalyst was characterized by several analytical techniques such as SEM, XRD, and FTIR. The effect of various parameters was studied including catalyst loading, mole ratio, to achieve excellent selectivity and yields in 80–90%. Significantly, the present protocol offers the use of an inexpensive and environmentally friendly catalyst and simple workup. The simplicity of the procedure, excellent yield of the products, and the recyclability of the catalyst are the main advantages of this method. Ammonium sulfate coated Hydro-Thermal-Carbone (HTC) (AS@HTC); an efficient and reused heterogeneous catalyst of the N-alkylation of pyrimidines was developed. Excellent selectivity and yields (80–90%) toward N1-alkylpyrimidines were achieved. Significantly, the present protocol offers the use of an inexpensive and environmentally friendly catalyst and simple workup.

  开发了一种利用硫酸铵包覆的水热碳（HTC）（AS@HTC）作为可重复使用的非均相催化剂，进行嘧啶N-烷基化的有效且经济的方法。通过SEM、XRD和FTIR等多种分析技术对催化剂进行了表征。研究了各种参数的影响，包括催化剂负载量、摩尔比，以实现80-90%的优异选择性和产率。值得注意的是，当前协议提供了使用廉价且环境友好的催化剂和简单后处理的优势。该方法的简单性、产品的优异产率以及催化剂的可回收性是其主要优点。硫酸铵包覆的水热碳（HTC）（AS@HTC）；开发了一种高效且可重复使用的非均相催化剂，用于嘧啶的N-烷基化。实现了对N1-烷基嘧啶的优异选择性和产率（80-90%）。值得注意的是，当前协议提供了使用廉价且环境友好的催化剂和简单后处理的优势。
• Preparation of 1,4-disubstituted-1,2,3-triazolo ribonucleosides by Na2CuP2O7 catalyzed azide-alkyne 1,3-dipolar cycloaddition
  作者：Hanane Elayadi、Mohamed Mesnaoui、Brent E. Korba、Michael Smietana、Jean Jacques Vasseur、John A. Secrist、Hassan B. Lazrek

  DOI：10.3998/ark.5550190.0013.807

  日期：——

  In this study, we describe the synthesis of 1,4-disustituted-1,2,3-triazolo-ribonucleosides by means of 1,3-dipolar cycloaddition between various N-1 propargyl-pyrimidines and 1’-azido2’,3’,5’-tri-O-benzoylribose catalyzed by Na2CuP2O7/sodium ascorbate. All obtained compounds were evaluated for their anti-HCV activity in vitro.

  在这项研究中，我们描述了通过各种 N-1 炔丙基嘧啶和 1'-叠氮基 2',3' 之间的 1,3-偶极环加成反应合成 1,4-二取代-1,2,3-三唑并核糖核苷Na2CuP2O7/抗坏血酸钠催化的,5'-三-O-苯甲酰核糖。对所有获得的化合物进行体外抗HCV活性评价。
• Synthesis of 1,2,3-Triazolyl Nucleoside Analogs as Potential Anti-Influenza A (H3N2 Subtype) Virus Agents
  作者：Hanane Elayadi、Michael Smietana、Jean J. Vasseur、Jan Balzarini、Hassan B. Lazrek

  DOI：10.1002/ardp.201300260

  日期：2014.2

  corresponding 1,4‐disubstituted 1,2,3‐triazoles in good yield. All compounds 16–23 were evaluated for their antiviral activity in vitro. Compound 18 showed moderate inhibition against influenza virus A (H3N2).

  用二氯化铜和碘化钾 (CuCl2/KI/K10) 浸渍的蒙脱石 K10 作为催化剂用于叠氮化物和炔丙基核碱基的环加成反应，以良好的收率提供相应的 1,4-二取代 1,2,3-三唑。对所有化合物 16-23 的体外抗病毒活性进行了评估。化合物 18 对流感病毒 A (H3N2) 表现出中等抑制作用。
• Triazole pyrimidine nucleosides as inhibitors of Ribonuclease A. Synthesis, biochemical, and structural evaluation
  作者：Vanessa Parmenopoulou、Demetra S.M. Chatzileontiadou、Stella Manta、Stamatina Bougiatioti、Panagiotis Maragozidis、Dimitra-Niki Gkaragkouni、Eleni Kaffesaki、Anastassia L. Kantsadi、Vassiliki T. Skamnaki、Spyridon E. Zographos、Panagiotis Zounpoulakis、Nikolaos A.A. Balatsos、Dimitris Komiotis、Demetres D. Leonidas

  DOI：10.1016/j.bmc.2012.09.067

  日期：2012.12

  inhibition constant (Ki) values with the ones having a triazolo linker being more potent than the ones without. The most potent of these is 1-[(β-d-ribofuranosyl)-1,2,3-triazol-4-yl]uracil being with Ki = 1.6 μM. The high resolution X-ray crystal structures of the RNase A in complex with three most potent inhibitors of these inhibitors have shown that they bind at the enzyme catalytic cleft with the

  已合成并表征了五个呋喃核糖基嘧啶核苷及其相应的1,2,3-三唑衍生物。已经通过生化分析和X射线晶体学研究了它们对核糖核酸酶A的抑制作用。这些化合物是具有低μM抑制常数（K i）值的有效的RNase A竞争性抑制剂，具有三唑连接子的化合物比没有三唑连接子的化合物更有效。其中最有效的是与K i有关的1-[（β- d-呋喃呋喃糖基）-1,2,3-三唑-4-基]尿嘧啶 = 1.6μM。RNase A与三种最强抑制剂的复合物的高分辨率X射线晶体结构显示，它们在酶催化裂隙处与B 1亚位处的嘧啶核苷结合，而三唑基团在主要亚位处结合P 1，其中发生P-O5'键断裂，并且核糖位于亚位点P 1和P 0之间的界面利用与两个子站点中的残基的相互作用。还研究了在抑制力的5-嘧啶位置上的取代基的作用，结果表明，在该位置上的任何添加都会导致抑制剂的效率降低。这些RNase A复合物与其他类似的RNase A-配体复合物