5'-(methylamino)-5'-deoxythymidine | 75191-50-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 2 '，5'-二脱氧核苷
• 英文名称: 5'-(methylamino)-5'-deoxythymidine
• 英文别名: 5'-deoxy-5'-(methylamino)thymidine；5'-deoxy-5'-methylaminothymidine；5'-methylamino-5'-deoxythimidine；1-[(2R,4S,5R)-4-hydroxy-5-(methylaminomethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 75191-50-3
• 化学式: C₁₁H₁₇N₃O₄
• 分子量: 255.274
• InChiKey: SMLUVDLCTDSENP-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  90.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5'-(methylamino)-5'-deoxythymidine 在 4-二甲氨基吡啶 、 TEA 、 四丁基氟化铵 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 四氢呋喃 、 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.25h， 生成
  参考文献：
  名称：

  寡聚脱氧核苷酸中酰胺键连接的胸苷二聚体的合成和杂交特性

  摘要：

  已经制备了通过酰胺或N-甲基酰胺键连接的胸苷二聚体。通过固相合成将二聚体各自掺入DNA的正常链中三次。热变性研究表明，这些修饰几乎不会引起DNA：RNA双链体的不稳定。

  DOI：

  10.1016/s0040-4039(00)73923-2
• 作为产物：
  描述：

  beta-胸苷 以 吡啶 、 水 为溶剂， 反应 3.0h， 生成 5'-(methylamino)-5'-deoxythymidine
  参考文献：
  名称：

  寡聚脱氧核苷酸中酰胺键连接的胸苷二聚体的合成和杂交特性

  摘要：

  已经制备了通过酰胺或N-甲基酰胺键连接的胸苷二聚体。通过固相合成将二聚体各自掺入DNA的正常链中三次。热变性研究表明，这些修饰几乎不会引起DNA：RNA双链体的不稳定。

  DOI：

  10.1016/s0040-4039(00)73923-2

文献信息

• Reactive 5'-substituted thymidine derivatives as potential inhibitors of nucleotide biosynthesis
  作者：Robert D. Elliott、R. Wallace Brockman、John A. Montgomery

  DOI：10.1021/jm00156a025

  日期：1986.6

  Fourteen derivatives of thymidine substituted at the 5'-position with haloacetamido (2-4), 2- and 3-bromopropionamido (5 and 6), bromoacetoxy (7), O-mesylglycolamido (8), bromo- and chloro-N-methylacetamido (10 and 11), bromomethanesulfonamido (12), ethyloxamido (13), 4- and 3-(fluorosulfonyl)benzamido (14 and 15), and (phenoxycarbonyl)amino (16) groups have been synthesized and evaluated as potential

  胸腺嘧啶的十四个衍生物在5'-位被卤代乙酰氨基（2-4），2-和3-溴丙酰胺基（5和6），溴代乙酰氧基（7），O-甲磺酰基糖胺基（8），溴代和氯代N-取代已合成了甲基乙酰胺基（10和11），溴甲烷磺酰胺基（12），乙基草酰胺基（13），4-和3-（氟磺酰基）苯甲酰胺基（14和15）和（苯氧羰基）氨基（16）基团，并被评估为潜在的抑制剂代谢嘌呤和嘧啶核苷的酶。比较了这些核苷与巯基乙醇在pH 7下的反应速率，并与生物活性有关。化合物2、3和7对培养中的H.Ep.-2和L1210细胞具有细胞毒性，而5'-（溴和碘乙酰氨基）-5'-脱氧胸苷（2和3）对小鼠的P388白血病表现出良好的活性。
• Synthesis and antineoplastic activity of a novel series of phosphoramide mustard analogs of pyrimidine deoxyribonucleosides
  作者：Tai-Shun Lin、Paul H. Fischer、William H. Prusoff

  DOI：10.1021/jm00185a018

  日期：1980.11

  derivatives of pyrimidine deoxyribonucleosides (6-9) has been synthesized from the corresponding amino nucleosides. Our preliminary findings have shown that three of these cyclophosphamide nucleoside analogues, 6, 7, and 9, have potent inhibitory effects on the replication of L1210 cells in vitro (ED50 = 1.2-1.5 x 10(-5) M). Since cyclophosphamide (cytoxan) has no cytotoxicity under these conditions, our

  从相应的氨基核苷合成了一系列新的嘧啶脱氧核糖核苷（6-9）环磷酰胺衍生物。我们的初步发现表明，这些环磷酰胺核苷类似物中的三个（6、7和9）对体外L1210细胞的复制具有有效的抑制作用（ED50 = 1.2-1.5 x 10（-5）M）。由于环磷酰胺（cytoxan）在这些条件下没有细胞毒性，因此我们的发现表明这些新型磷酰胺衍生物具有不同寻常的生物学特性，其中可能包括独特的激活方式。
• Method, system and reagents for DNA sequencing
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US05242796A1

  公开（公告）日：1993-09-07

  A DNA sequencing system and method are described to detect the presence of radiant energy emitted from different excited reporter dye-labeled species (DNA fragments) following separation in time and/or space, and the identity of the species which emit radiant energy closely spaced in wavelength. Functions of the emitted energy are obtained which vary over the wavelengths of the closely spaced spectra in different senses and the functions ratioed, whereby the ratio is indicative of the identity of the DNA fragments. The emitting portion of the reporter-labeled DNA fragment is preferably one of a family of fluorescent dyes based on 9-carboxyethyl-6-hydroxy-3-oxo-3 H-xanthene. These xanthene dyes are covalently attached to the DNA fragments through the carboxylic acid functionality, preferably via an amide linkage. The dyes may be protected by including an alkoxy group at the 9-position. A spacer may be inserted between the dye and the amine. The fluorescent dye preferably is attached to the DNA chain terminators and provides many advantages. Thus only DNA sequencing fragments resulting from bona fide termination events will carry a reporter. The DNA sequencing may also be labeled using the xanthene dyes which have general utility as fluorescent labels. Also acyclonucleoside triphosphates are described as being useful as chain terminators in DNA sequencing using a modification of the Sanger method.

  本文描述了一种DNA测序系统和方法，用于检测不同激发染料标记的物种（DNA片段）分离后发出的辐射能量的存在，并且在时间和/或空间上，以及在波长密集的发射能量的物种的身份上，获得变化的发射能量的功能。通过对函数进行比率，比率表明DNA片段的身份。最好的发射染料标记DNA片段的发射部分是基于9-羧基乙基-6-羟基-3-氧代-3H-黄酮的荧光染料家族之一。这些黄酮染料通过羧酸功能与DNA片段共价连接，最好通过酰胺连接。染料可以通过在9位点包括烷氧基来保护。染料和胺之间可以插入一个间隔物。荧光染料最好连接到DNA链终止子上，并提供许多优点。因此，只有由真正终止事件产生的DNA测序片段才会携带报告者。DNA测序也可以使用具有荧光标记通用性的黄酮染料进行标记。此外，本文还介绍了使用Sanger方法的改进来使用无环核苷酸三磷酸盐作为DNA测序中的链终止剂的方法。
• Method systems and reagents for DNA sequencing
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US05306618A1

  公开（公告）日：1994-04-26

  A DNA sequencing system and method are described to detect the presence of radiant energy emitted from different excited reporter dye-labeled species (DNA fragments) following separation in time and/or space, and the identity of the species which emit radiant energy closely spaced in wavelength. Functions of the emitted energy are obtained which vary over the wavelengths of the closely spaced spectra in different senses and the functions ratioed, whereby the ratio is indicative of the identity of the DNA fragments. The emitting portion of the reporter-labeled DNA fragment is preferably one of a family of fluorescent dyes based on 9-carboxyethyl-6-hydroxy-3-oxo-3H-xanthene. These xanthene dyes are covalently attached to the DNA fragments through the carboxylic acid functionality, preferably via an amide linkage. The dyes may be protected by including an alkoxy group at the 9-position. A spacer may be inserted between the dye and the amine. The fluorescent dye preferably is attached to the DNA chain terminators and provides many advantages. Thus only DNA sequencing fragments resulting from bona fide termination events will carry a reporter. The DNA sequencing may also be labeled using the xanthene dyes which have general utility as fluorescent labels. Also acyclonucleoside triphosphates are described as being useful as chain terminators in DNA sequencing using a modification of the Sanger method.

  本文描述了一种DNA测序系统和方法，用于检测不同激发报告染料标记物（DNA片段）在时间和/或空间分离后发出的辐射能量的存在，并且发出辐射能量的标记物种类在波长上密集排列。通过获取在不同光谱密集区域波长上变化的发射能量的功能，并对这些功能进行比率，从而比率指示DNA片段的标识。最好的报告染料标记DNA片段的发射部分是基于9-羧基乙基-6-羟基-3-氧代-3H-黄色素的一族荧光染料之一。这些黄色素染料通过羧酸官能团，最好通过酰胺键连接到DNA片段上。染料可以通过在9位位置包含烷氧基来保护。在染料和胺之间可以插入一个间隔物。荧光染料最好连接到DNA链终止子上，并提供许多优点。因此，只有由真正终止事件产生的DNA测序片段才会携带报告物。DNA测序也可以使用黄色素染料标记，这些染料具有荧光标记的通用性。此外，还描述了使用Sanger方法的修饰来使用无环核苷酸三磷酸盐作为DNA测序中的链终止剂。
• DNA sequencing method using acyclonucleoside triphosphates
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US05558991A1

  公开（公告）日：1996-09-24

  Acyclonucleoside triphosphates are described as being useful as chain terminators in DNA sequencing using a modification of the Sanger method.

  Acyclonucleoside三磷酸被描述为在使用Sanger方法的DNA测序中作为链终止剂而有用。