4-methyl-5-(thiophen-3-yl)-N7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine | 1536111-27-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡咯并嘧啶核苷和核苷酸
• 英文名称: 4-methyl-5-(thiophen-3-yl)-N7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
• 英文别名: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[4-methyl-5-(3-thienyl)pyrrolo[2,3-d]pyrimidin-7-yl]tetrahydrofuran-3,4-diol；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(4-methyl-5-thiophen-3-ylpyrrolo[2,3-d]pyrimidin-7-yl)oxolane-3,4-diol
• CAS: 1536111-27-9
• 化学式: C₁₆H₁₇N₃O₄S
• 分子量: 347.395
• InChiKey: UCSAHRZFGUDEPF-XKVFNRALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-methyl-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 在 N-溴代丁二酰亚胺(NBS) 、 trisodium tris(3-sulfophenyl)phosphine 、 palladium diacetate 、 sodium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.67h， 生成 4-methyl-5-(thiophen-3-yl)-N7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  Synthesis, Cytostatic, Antimicrobial, and Anti-HCV Activity of 6-Substituted 7-(Het)aryl-7-deazapurine Ribonucleosides

  摘要：

  A series of 80 7-(het)aryl- and 7-ethyny1-7-deazapurine ribonucleosides bearing a methoxy, methylsulfanyl, methylamino, dimethylamino, methyl, or oxo group at position 6, or 2,6-disubstituted derivatives bearing a methyl or amino group at position 2, were prepared, and the biological activity of the compounds was studied and compared with that of the parent 7-(het)ary1-7-deazaadenosine series. Several of the compounds, in particular 6-substituted 7-deazapurine derivatives bearing a furyl or ethynyl group at position 7, were significantly cytotoxic at low nanomolar concentrations whereas most were much less potent or inactive. Promising activity was observed with some compounds against Mycobacterium bovis and also against hepatitis C virus in a replicon assay.

  DOI：

  10.1021/jm4018948

文献信息

• NOVEL SUBSTITUTED 7-DEAZAPURINE RIBONUCLEOSIDES FOR THERAPEUTIC USES
  申请人：Institute of Organic Chemistry and Biochemistry ASCR, v.v.i.

  公开号：US20160159844A1

  公开（公告）日：2016-06-09

  Compounds of Formula I and a pharmaceutically acceptable salt thereof, an optical isomer thereof, or a mixture of optical isomers thereof, as well as compositions which include such compounds and therapeutic methods that utilize such compounds and/or compositions.

  化合物I的盐，其药用上可以接受的盐，其光学异构体或其光学异构体的混合物，以及包括这些化合物的组合物和利用这些化合物和/或组合物的治疗方法。
• Exploration of 6-methyl-7-(Hetero)Aryl-7-Deazapurine ribonucleosides as antileishmanial agents
  作者：Cai Lin、Izet Karalic、An Matheeussen、Pim-Bart Feijens、Fabian Hulpia、Louis Maes、Guy Caljon、Serge Van Calenbergh

  DOI：10.1016/j.ejmech.2022.114367

  日期：2022.7

  allocated for antileishmanial drug discovery. The Leishmania parasite is deficient in de novo purine synthesis, and therefore acquires purines from the host and processes these using a purine salvage pathway. By making use of purine transport systems and interfering with this salvage pathway, purine (nucleoside) analogues might exert a selective detrimental impact on its growth and survival. In vitro screening

  利什曼病在非洲、亚洲、美洲和南欧的热带和亚热带地区导致高死亡率和高发病率，并以多种临床表现为特征。作为一种被忽视的热带病，有限的资源被分配用于抗寄生虫药物的发现。利什曼原虫缺乏从头合成嘌呤，因此从宿主获取嘌呤并使用嘌呤回收途径进行处理。通过利用嘌呤转运系统并干扰这种补救途径，嘌呤（核苷）类似物可能对其生长和存活产生选择性的有害影响。体外筛选内部嘌呤核苷库和类似物合成提供了 6-methyl-7-(2-pyridyl)-7-deazapurine ribonucleoside 类似物18作为有希望的打击。7-取代基的优化提供了31和32，它们显示出对野生型和抗性L. infantum 、细胞内无鞭毛体和细胞外前鞭毛体形式的有效活性，并且对原代小鼠巨噬细胞 (Mφ) 和 MRC-5 细胞具有良好的选择性。受32良好的体外代谢稳定性的鼓舞，使用早期治疗性L. infantum进行了一项体内研究。仓鼠模型。当以
• US9586986B2
  申请人：——

  公开号：US9586986B2

  公开（公告）日：2017-03-07
• Synthesis, Cytostatic, Antimicrobial, and Anti-HCV Activity of 6-Substituted 7-(Het)aryl-7-deazapurine Ribonucleosides
  作者：Petr Nauš、Olga Caletková、Petr Konečný、Petr Džubák、Kateřina Bogdanová、Milan Kolář、Jana Vrbková、Lenka Slavětínská、Eva Tloušt’ová、Pavla Perlíková、Marián Hajdúch、Michal Hocek

  DOI：10.1021/jm4018948

  日期：2014.2.13

  A series of 80 7-(het)aryl- and 7-ethyny1-7-deazapurine ribonucleosides bearing a methoxy, methylsulfanyl, methylamino, dimethylamino, methyl, or oxo group at position 6, or 2,6-disubstituted derivatives bearing a methyl or amino group at position 2, were prepared, and the biological activity of the compounds was studied and compared with that of the parent 7-(het)ary1-7-deazaadenosine series. Several of the compounds, in particular 6-substituted 7-deazapurine derivatives bearing a furyl or ethynyl group at position 7, were significantly cytotoxic at low nanomolar concentrations whereas most were much less potent or inactive. Promising activity was observed with some compounds against Mycobacterium bovis and also against hepatitis C virus in a replicon assay.