5'-chloro-5'-deoxyuridine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 5'-chloro-5'-deoxyuridine
• 英文别名: 5'-Desoxy-5'-chlor-uridin；1-[(2R,3R,4S,5S)-5-(chloromethyl)-3,4-dihydroxyoxolan-2-yl]pyrimidine-2,4-dione
• 化学式: C₉H₁₁ClN₂O₅
• 分子量: 262.65
• InChiKey: BQPRXEHWLMFKLL-XVFCMESISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5'-chloro-5'-deoxyuridine 在 吡咯 、 三苯基膦 、 四甲基胍 作用下， 以 溶剂黄146 为溶剂， 反应 8.0h， 生成 5'-thio-5'-deoxyuridine
  参考文献：
  名称：

  9-(4-Methoxyphenyl)xanthen-9-thiol: A useful reagent for the preparation of thiols

  摘要：

  Treatment of 5' -chloro-5' -deoxynucleosides (5) with the conjugate base of 9-(4-methoxyphenyl)xanthen-9-thiol (3b), followed by acid-promoted removal of the 5'-s-[9-(4-methoxyphenyl)xanthen-9-yl] group in the presence of pyrrole gives the corresponding 5'-deoxy-5'-mercaptonucleosides (7) in good yields.

  DOI：

  10.1016/s0040-4039(00)88523-8
• 作为产物：
  描述：

  尿嘧啶核苷 在 六甲基磷酰三胺 、 氯化亚砜 作用下， 以55%的产率得到5'-chloro-5'-deoxyuridine
  参考文献：
  名称：

  9-(4-Methoxyphenyl)xanthen-9-thiol: A useful reagent for the preparation of thiols

  摘要：

  Treatment of 5' -chloro-5' -deoxynucleosides (5) with the conjugate base of 9-(4-methoxyphenyl)xanthen-9-thiol (3b), followed by acid-promoted removal of the 5'-s-[9-(4-methoxyphenyl)xanthen-9-yl] group in the presence of pyrrole gives the corresponding 5'-deoxy-5'-mercaptonucleosides (7) in good yields.

  DOI：

  10.1016/s0040-4039(00)88523-8

文献信息

• Nucleic acid related compounds. 66. Improved syntheses of 5′-chloro-5′-deoxy- and 5′-<i>S</i>-aryl(or alkyl)-5′-thionucleosides
  作者：Morris J. Robins、Fritz Hansske、Stanislaw F. Wnuk、Tadashi Kanai

  DOI：10.1139/v91-217

  日期：1991.9.1

  Treatment of ribonucleosides with thionyl chloride/pyridine/acetonitrile (0 °C to ambient temperature) resulted in essentially quantitative formation of 5′-chloro-5′-deoxy-2′,3′-O-sulfinylnucleoside derivatives. These diastereomeric sulfite esters underwent deprotection readily with aqueous methanolic ammonia. This gave 5′-chloro-5′-deoxynucleosides without use of the suspected carcinogen, hexamethylphosphoramide (HMPA). Nucleophilic displacement with sodium thiolates in dimethylformamide (−30 °C to ambient temperature) gave 5′-S-aryl(or alkyl)-5′-thionucleosides in high yields. Treatment of ribonucleosides with thionyl chloride/acetonitrile without pyridine followed by aqueous work-up gave diastereomeric 2′,3′-O-sulfinylnucleosides with an unmodified 5′-hydroxyl group. Diagnostic NMR shifts for cyclic sulfite ester stereochemistry are noted. Key words: adenosine, 5′-S-aryl(or alkyl)-5′-thionucleosides, 5′-chloro-5′-deoxynucleosides, uridine, nucleosides.

  使用硫酰氯/吡啶/乙腈（0°C至室温）处理核糖核苷可基本定量形成5'-氯-5'-脱氧-2'，3'-O-亚磺酰核苷衍生物。这些对映异构的亚硫酸酯酯可以轻松地通过甲醇氨水溶液去保护基。这样就可以不使用疑似致癌物六甲基磷酰胺（HMPA）制备5'-氯-5'-脱氧核苷。在二甲基甲酰胺中，通过钠硫醇的亲核置换反应（-30°C至室温），可以高产得到5'-S-芳基（或烷基）-5'-硫代核苷。使用硫酰氯/乙腈而不是吡啶处理核糖核苷，然后进行水处理，可以得到未修饰的5'-羟基核苷的对映异构的2'，3'-O-亚磺酰核苷。文中还提到了环状亚硫酸酯立体化学的诊断NMR位移。关键词：腺苷，5'-S-芳基（或烷基）-5'-硫代核苷，5'-氯-5'-脱氧核苷，尿苷，核苷。
• [EN] USE OF A DHODH INHIBITOR IN COMBINATION WITH AN INHIBITOR OF PYRIMIDINE SALVAGE<br/>[FR] UTILISATION D'UN INHIBITEUR DE DHODH EN ASSOCIATION AVEC UN INHIBITEUR DE RÉCUPÉRATION PYRIMIDIQUE
  申请人：UNIV LELAND STANFORD JUNIOR

  公开号：WO2017117006A1

  公开（公告）日：2017-07-06

  Compounds and methods are provided for the treatment of pathogenic virus infections or cancer. The formulations combine an inhibitor of de novo pyrimidine synthesis, and an inhibitor of a pyrimidine salvage pathway enzyme.

  提供了用于治疗病原病毒感染或癌症的化合物和方法。该配方组合了一种新生嘧啶合成抑制剂和一种嘧啶救助途径酶抑制剂。
• Nucleosides. IV. Synthesis and reactions of 2',3',5'-trichloro-2',3',5'-trideoxy-2',3'-secouridines.
  作者：KOSAKU HIROTA、TETSUO TOMISHI、YOSHIFUMI MAKI

  DOI：10.1248/cpb.36.1298

  日期：——

  2', 3', 5'-Trichloro-2', 3', 5'-trideoxy-2', 3'-secouridines (2a, b) were synthesized from uridine or 5-fluorouridine by a combination of sodium metaperiodate oxidation, sodium borohydride reduction, and chlorination with Vilsmeier-Haack reagent. Reaction of 2a, b with base gave some new pyrimidine acyclonucleosides (3-5) and (uracil-l-yl)-1, 4-dioxanes (8, 9). The preparation of 5'-chloro-5'-deoxy-2', 3'-secouridine (11) from 5'-chloro-5'-deoxyuridine (10) and its conversion into (uracil-l-yl)-1, 4-dioxane 12 and 5'-deoxy-2', 3'-secouridine (13) are also described.

  2', 3', 5'-Trichloro-2', 3', 5'-trideoxy-2', 3'-secouridines（2a, b）是由尿苷或 5-氟尿苷通过偏碘酸钠氧化、硼氢化钠还原和 Vilsmeier-Haack 试剂氯化组合合成的。将 2a 和 b 与碱反应，可得到一些新的嘧啶无环核苷（3-5）和（尿嘧啶-l-基）-1，4-二氧杂环（8，9）。此外，还介绍了由 5'-chloro-5'-deoxyuridine (10) 制备 5'-chloro-5'-deoxy-2', 3'-secouridine (11) 以及将其转化为 (尿嘧啶-l-基)-1, 4-二氧杂环12 和 5'-deoxy-2', 3'-secouridine (13)的方法。
• Enzymatic production of cytosinic nucleoside analogues
  申请人：Plasmia Biotech, S.L.

  公开号：EP2883959A1

  公开（公告）日：2015-06-17

  The invention relates to a new synthesis process of cytosine nucleoside analogues by using nucleoside phosphorylase enzymes, particularly Pyrimidin Nucleoside Phosphorylases (PyNPs) or mixtures of Purine Nucleoside Phosphorylases (PNPs) and PyNPs.

  本发明涉及使用核苷酸磷酸化酶，特别是嘧啶核苷酸磷酸化酶(PyNPs)或嘧啶核苷酸磷酸化酶(PyNPs)和嘌呤核苷酸磷酸化酶(PNPs)混合物的新型合成胞嘧啶核苷类似物的过程。
• F-substituted-3-.beta.-D-ribofuranosyl-3H-imidazo[4,5-b]pyridines and
  申请人：Burroughs Wellcome Co.

  公开号：US04780452A1

  公开（公告）日：1988-10-25

  This invention discloses a group of compounds of formula (I) ##STR1## wherein R.sup.1 is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, COOR.sup.4 (R.sup.4 is H or C.sub.1-4 alkyl) or trifluoromethyl; R.sup.2, R.sup.5 and R.sup.6 are the same or different and can be hydrogen, hydroxy, OCOR.sup.7 (wherein R.sup.7 is hydrogen, C.sub.1-4 alkyl, phenyl optionally substituted) or halo; and R.sup.3 is hydrogen, COR.sup.4, C.sub.3-6 cycloalkyl or C.sub.1-4 alkyl or alkenyl; R.sup.2 may also be a phosphate group and pharmaceutically acceptable salts thereof which have been found to have analgesic activity. In addition, these compounds have antiinflammatory, antipyretic, antihypertensive and vasodilatory activity in varying degrees. Some of these compounds also have antiprotozoal and antiviral properties.

  该发明披露了一组化合物，其化学式为（I）##STR1##其中R.sup.1是氢，卤素，C.sub.1-4烷基，C.sub.1-4烷氧基，COOR.sup.4（其中R.sup.4是H或C.sub.1-4烷基）或三氟甲基; R.sup.2，R.sup.5和R.sup.6相同或不同，可以是氢，羟基，OCOR.sup.7（其中R.sup.7是氢，C.sub.1-4烷基，苯基可选择性取代）或卤素; 而R.sup.3是氢，COR.sup.4，C.sub.3-6环烷基或C.sub.1-4烷基或烯基; R.sup.2也可以是磷酸盐基及其药学上可接受的盐，已发现具有镇痛活性。此外，这些化合物具有不同程度的抗炎，退烧，降压和扩血管活性。其中一些化合物还具有抗原虫和抗病毒特性。