5'-deoxy-5-iodocytidine | 216450-15-6

• 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'-deoxy-5-iodocytidine
• 英文别名: 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-iodopyrimidin-2-one
• CAS: 216450-15-6
• 化学式: C₉H₁₂IN₃O₄
• 分子量: 353.116
• InChiKey: YMFSDPSSPUNGFD-ZIYNGMLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5'-deoxy-5-iodocytidine 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 5'-deoxy-2',3'-bis-O-(tert-butyldimethylsilyl)-5-cyanocytidine
  参考文献：
  名称：

  Design and synthesis of the tumor-activated prodrug of dihydropyrimidine dehydrogenase (DPD) inhibitor, RO0094889 for combination therapy with capecitabine

  摘要：

  A series of tumor-activated prodrugs of the inhibitors of dihydropyrimidine dehydrogenase (DPD), an enzyme catabolizing 5-fluorouracil (5-FU: 4g), has been designed and synthesized. RO0094889 (11c) is a prodrug of 5-vinyluracil (4c), a known DPD inhibitor, and was designed to generate 4c selectively in tumor tissues by sequential conversion of 11c by three enzymes: esterase, cytidine deaminase and thymidine phosphorylase, the latter two of which are known to be highly expressed in various tumor tissues. When capecitabine (1), a tumor-activated prodrug of 5-FU, was co-administered orally with 11c, 5-FU in tumor tissues was significantly increased with only a slight increase of 5-FU in plasma as compared with oral capecitabine alone. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)01082-x
• 作为产物：
  描述：

  2',3'-di-O-acetyl-5'-deoxy-5-iodocytidine 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以100%的产率得到5'-deoxy-5-iodocytidine
  参考文献：
  名称：

  Design and synthesis of the tumor-activated prodrug of dihydropyrimidine dehydrogenase (DPD) inhibitor, RO0094889 for combination therapy with capecitabine

  摘要：

  A series of tumor-activated prodrugs of the inhibitors of dihydropyrimidine dehydrogenase (DPD), an enzyme catabolizing 5-fluorouracil (5-FU: 4g), has been designed and synthesized. RO0094889 (11c) is a prodrug of 5-vinyluracil (4c), a known DPD inhibitor, and was designed to generate 4c selectively in tumor tissues by sequential conversion of 11c by three enzymes: esterase, cytidine deaminase and thymidine phosphorylase, the latter two of which are known to be highly expressed in various tumor tissues. When capecitabine (1), a tumor-activated prodrug of 5-FU, was co-administered orally with 11c, 5-FU in tumor tissues was significantly increased with only a slight increase of 5-FU in plasma as compared with oral capecitabine alone. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)01082-x

文献信息

• [EN] 5'-DEOXYCYTIDINE DERIVATIVES<br/>[FR] DERIVES DE 5'-DEOXYCYTIDINE
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：WO1999040099A1

  公开（公告）日：1999-08-12

  (EN) Compounds of general formula (I) wherein R1 is each independently hydrogen or a group easily hydrolyzable under physiological conditions; R2 is -(CH2)n-cycloalkyl (wherein cycloalkyl consists of 3 to 5 carbon atoms, n is an integer from 0 to 4), heteroaryl-(lower-alkyl), (lower-alkoxy)-(lower-alkyl), aryloxy-(lower-alkyl), aralkyloxy-(lower-alkyl), (lower-alkylthio)-(lower-alkyl), arylthio-(lower-alkyl), araykylthio-(lower-alkyl), oxo-(lower-alkyl), acylamino-(lower-alkyl), cyclic amino-(lower-alkyl), (2-oxocyclic amino)-(lower-alkyl) wherein the alkylene chain may be further substituted with one or two lower-alkyl group(s) and R3 is iodo, a vinyl or ethynyl group [which groups may be substituted with halogen atom(s), C1-4 alkyl, cycloalkyl, aralkyl, or an aromatic ring which may have one or more hetero atom(s)], are useful in the treatment of malignant diseases and can also be administered together with 5-fluorouracil or derivatives thereof to enhance the antitumour activity of the latter.(FR) L'invention concerne des composés représentés par la formule (I). Dans cette formule, R1 représente hydrogène ou un groupe facilement hydrolysable dans des conditions physiologiques; R2 représente -(CH2)n-cycloalkyle [où cycloalkyle est constitué de 3 à 5 atomes de carbone, n est un nombre entier compris entre 0 et 4], hétéroaryle-(alkyle inférieur), (alcoxy inférieur)-(alkyle inférieur), aryloxy-(alkyle inférieur), aralkyloxy-(alkyle inférieur), (alkylthio inférieur)-(alkyle inférieur), arylthio-(alkyle inférieur), araykylthio-(alkyle inférieur), oxo-(alkyle inférieur), acylamino-(alkyle inférieur), amino cyclique-(alkyle inférieur), (amino 2-oxocyclic)- (alkyle inférieur), où la chaîne alkylène peut être ensuite substituée par un ou deux groupes alkyle inférieur et R3 représente iodo, un groupe vinyle ou éthynyle [lesquels groupes peuvent être substitués par des atomes d'halogène, C1-4 alkyle, cycloalkyle, aralkyle ou un noyau aromatique pouvant comportant un ou plusieurs atomes hétéro]. Ces composés sont utilisés pour traiter des affections malignes et peuvent être administrés avec 5-fluoro-uracil ou des dérivés de celui-ci de manière à améliorer l'activité antitumeur desdits composés.

  化合物的一般式（I），其中R1分别为氢或在生理条件下容易水解的基团；R2为-(CH2)n-环烷基（其中环烷基由3到5个碳原子组成，n为0到4的整数），杂环芳基-(较低烷基)，（较低烷氧）-（较低烷基），芳氧基-(较低烷基)，芳基烷氧基-(较低烷基)，（较低烷硫基）-（较低烷基），芳基硫基-(较低烷基)，芳基烷硫基-(较低烷基)，氧代-(较低烷基)，酰基氨基-(较低烷基)，环状氨基-(较低烷基)，（2-氧代环状氨基）-（较低烷基），其中烷基链可以进一步取代一个或两个较低烷基团，R3为碘、乙烯基或乙炔基[这些基团可以被卤素原子、C1-4烷基、环烷基、芳基烷基或一个或多个杂环原子的芳香环所取代]，用于治疗恶性疾病，并可与5-氟尿嘧啶或其衍生物一起给予，以增强后者的抗肿瘤活性。
• Chemical compounds
  申请人：——

  公开号：US20040248852A1

  公开（公告）日：2004-12-09

  The present invention concerns compounds of formula (I), and pharmaceutically acceptable salts or solvates thereof, or solvates of such salts, 1 which compounds inhibit carboxypeptidase U and thus can be used in the prevention and treatment of diseases where inhibition of carboxypeptidase U is beneficial. In further aspects, the invention relates to compounds of the invention for use in therapy; to processes for preparation of such new compounds; to pharmaceutical compositions containing at least one compound of the invention, or a pharmaceutically acceptable salt or solvate thereof, as active ingredient; and to the use of the active compounds in the manufacture of medicaments for the medical use indicated above.

  本发明涉及式（I）的化合物，以及其药学上可接受的盐或溶剂化物，或这种盐的溶剂化物，1这些化合物抑制羧肽酶U，因此可用于预防和治疗抑制羧肽酶U有益的疾病。在进一步方面，本发明涉及本发明中化合物的治疗用途；制备这种新化合物的过程；包含本发明中至少一种化合物或其药学上可接受的盐或溶剂化物的制药组合物作为活性成分；以及将活性化合物用于制造上述医疗用途的药物。
• 5'-Deoxy-cytidine derivatives
  申请人：F. Hoffmann-La Roche AG

  公开号：EP0882734B1

  公开（公告）日：2009-08-26
• 5'-DEOXYCYTIDINE DERIVATIVES
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1060183A1

  公开（公告）日：2000-12-20
• Phosphor containing compounds with antithrombitic activity
  申请人：AstraZeneca AB

  公开号：EP1432718B1

  公开（公告）日：2009-09-02