D-(-)-carbodine | 71184-20-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: D-(-)-carbodine
• 英文别名: (-)-Carbodine；cytidine；CC；(1R,2S,3R,4R)-1-[2,3-dihydroxy-4-(hydroxymethyl)-cyclopentan-1-yl]cytosine；Carbodine；4-amino-1-[(1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl]pyrimidin-2-one
• CAS: 71184-20-8
• 化学式: C₁₀H₁₅N₃O₄
• 分子量: 241.247
• InChiKey: UAZJPMMKWBPACD-GCXDCGAKSA-N

物化性质

• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  4

制备方法与用途

生物活性

Carbodine（ Carbocyclic cytidine）是一种广谱抗病毒药物，对DNA病毒、(+)RNA病毒、(-)RNA病毒、paramyxo、rhabdo和(±)RNA病毒均有活性。它通过靶向CTP合成酶，将UTP转换为CTP。体外实验显示，Carbodine在对抗流感病毒A0/PR-8/34和A2/Aichi/2/68方面表现出显著的抗病毒活性。

反应信息

• 作为反应物：
  描述：

  D-(-)-carbodine 在 吡啶 、 氯 作用下， 以 四氯化碳 为溶剂， 反应 44.0h， 生成 Acetic acid (1R,2S,3S,5S)-2-acetoxy-3-acetoxymethyl-5-(4-amino-5-chloro-2-oxo-2H-pyrimidin-1-yl)-cyclopentyl ester
  参考文献：
  名称：

  Carbocyclic analogs of 5-halocytosine nucleosides

  摘要：

  Carbocyclic analogues of 5-halocytosine nucleosides were prepared by direct halogenation of the carbocyclic analogues of cytidine, 2'-deoxycytidine, 3'-deoxycytidine, or ara-C. The 5-chloro and 5-bromo derivatives of the cytidine (carbodine) and of the 2'-deoxycytidine analogues and the 5-iodo derivatives of all four of the cytosine nucleoside analogues were prepared. All of the C-5-halocytosine nucleosides, as well as the parent C-cytosine nucleosides, were tested against a strain of herpes simplex virus type 1 (HSV-1) that induces thymidine kinase in host cells. Carbodine, 5-bromocarbodine, C-2'-deoxycytidine, C-5-bromo-2'-deoxycytidine, the four C-5-iodocytosine nucleosides, and C-ara-C inhibited replication of this strain of HSV-1 in cultured cells. Most of these compounds were tested also against the type 2 virus (HSV-2) in vitro and were active. The greatest activity observed was exerted by C-5-iodo-2'-deoxycytidine in inhibiting replication of HSV-1 in L929 cells. In tests against these DNA viruses, carbodine, a ribofuranoside analogue that had been shown previously to be highly active against human influenza A virus in vitro, was the most active compound against HSV-2 and one of the most active compounds against HSV-1 in Vero cells. 5-Bromocarbodine was active against influenza virus, but it was less active than carbodine.

  DOI：

  10.1021/jm00159a026
• 作为产物：
  描述：

  (3aR,6R,6aR)-6-(tert-butoxymethyl)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-one 在 palladium 10% on activated carbon 4-二甲氨基吡啶 、 sodium azide 、 2,4,6-三异丙基苯磺酰氯 、 cerium(III) chloride 、 氨 、 水 、 氢气 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， -78.0~140.0 ℃ 、241.32 kPa 条件下， 反应 65.5h， 生成 D-(-)-carbodine
  参考文献：
  名称：

  WO2008/124157

  摘要：

  公开号：
• 作为试剂：
  描述：

  (2X,4E)-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienal 在 D-(-)-carbodine 、 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以60%的产率得到β-Ionyliden-ethanol
  参考文献：
  名称：

  Cyclofarnesoids and methylhexanoids produced from β-carotene in Phycomyces blakesleeanus

  摘要：

  The oxidative cleavage of beta-carotene in the Mucorales produces three fragments of 18, 15, and 7 carbons, respective heads of three families of apocarotenoids: the methylhexanoids, the trisporoids, and the cyclofarnesoids (named after their 1,6-cyclofarnesane skeleton). The apocarotenoids are easily recognized because they are absent in white mutants unable to produce beta-carotene. In cultures of Phycomyces blakesleeanus we detected thirty-two apocarotenoids by LC, UV absorbance, and MS. With additional IR and NMR we identified two methylhexanoids and the eight most abundant cyclofarnesoids. Four of them were previously-unknown natural compounds, including 4-dihydrocyclofarnesine S, the most abundant cyclofarnesoid in young cultures. We arranged the apocarotenoids of the Mucorales in a scheme that helps classifying and naming them and suggests possible metabolites and biosynthetic pathways. We propose specific biosynthetic pathways for cyclofarnesoids and methylhexanoids based on structural comparisons, the time course of appearance of individual compounds, and the bioconversion of beta-apo12-carotenol, an early precursor, to three more oxygenated cyclofarnesoids by the white mutants. Some of the reactions occur spontaneously in the increasingly acidic culture media. Mating increased the contents of methylhexanoids and cyclofarnesoids by ca. threefold in young cultures and ca. twelvefold in old ones (five days); cyclofarnesine S, the most abundant cyclofarnesoid in old cultures, increased over one hundredfold. We found no differences between the sexes and no activity as sexual pheromones, but we suggest that methylhexanoids and cyclofarnesoids could mediate species-specific physiology and behavior. 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2016.01.013

文献信息

• Contrasting Behavior of Conformationally Locked Carbocyclic Nucleosides of Adenosine and Cytidine as Substrates for Deaminases
  作者：Victor E. Marquez、Gottfried K. Schroeder、Olaf R. Ludek、Maqbool A. Siddiqui、Abdallah Ezzitouni、Richard Wolfenden

  DOI：10.1080/15257770903091904

  日期：2009.8.11

  In addition to the already known differences between adenosine deaminase (ADA) and cytidine deaminase (CDA) in terms of their tertiary structure, the sphere of Zn+2 coordination, and their reverse stereochemical preference, we present evidence that the enzymes also differ significantly in terms of the North/South conformational preferences for their substrates and the extent to which the lack of the

  除了已知的腺苷脱氨酶 (ADA) 和胞苷脱氨酶 (CDA) 在三级结构、Zn+2 配位范围和反向立体化学偏好方面存在差异之外，我们还提供了证据表明这些酶在其底物的北/南构象偏好以及缺乏 O(4') 氧对碳环底物酶促脱氨动力学的影响程度。本研究中使用的碳环核苷底物具有柔性环戊烷环或刚性双环 [3.1.0] 己烷支架。
• Anti-HCV nucleoside derivatives
  申请人：——

  公开号：US20030008841A1

  公开（公告）日：2003-01-09

  The present invention comprises novel and known purine and pyrimidine nucleoside derivatives which have been discovered to be active against hepatitis C virus (HCV). The use of these derivatives for the treatment of HCV infection is claimed as are the novel nucleoside derivatives disclosed herein.

  本发明涉及新颖和已知的嘌呤和嘧啶核苷衍生物，已发现这些衍生物对丙型肝炎病毒（HCV）具有活性。本发明声明利用这些衍生物治疗HCV感染，以及本文所披露的新颖核苷衍生物。
• Carbocyclic analogs of cytosine nucleosides
  作者：Y. Fulmer Shealy、C. Allen O'Dell

  DOI：10.1002/jhet.5570170228

  日期：1980.3

  cytosine derivatives were frequently accompanied by small amounts of the corresponding N,N-dimethylcytosine derivatives, which could be removed by ion-exchange chromatography. Carbodine (VIa), the carbocyclic analog of cytidine, was obtained in 84% yield from the pure 4-chloropyrimidinone intermediate, after the latter was prepared by deoxychlorination in carbon tetrachloride. Carbodine has antileukemic

  由类似的尿嘧啶衍生物合成了胞苷，2'-脱氧胞苷和3'-脱氧胞苷的碳环类似物。该途径包括尿嘧啶衍生物的完全苯甲酰化，选择性除去连接在嘧啶环上的苯甲酰基，用二甲基甲酰胺-亚硫酰氯试剂将4-氧代转化为4-氯基以及用氯代氨酯取代氯基。甲醇氨中的氨基 当使用脱氧氯化反应的总产物时，所需的胞嘧啶衍生物常常伴随着少量的相应的N，N-二甲基胞嘧啶衍生物，可以通过离子交换色谱法除去。从纯的4-氯嘧啶酮中间体通过在四氯化碳中进行脱氧氯化制备后，以84％的收率获得了胞嘧啶核苷的类似物卡铂（VIa）。卡博定具有抗白血病，抗病毒和抗菌活性。
• CARBOCYCLIC COMPOUNDS AND METHODS FOR TREATING EMERGING DISEASE, INCLUDING INFLUENZA AND VENEZUELA EQUINE ENCEPHALITIS VIRUS
  申请人：Chu David

  公开号：US20100144664A1

  公开（公告）日：2010-06-10

  The present invention relates to the use of carbodine and 5-F carbodine and analogs thereof for use in the treatment or prophylaxis of influenza, in particular the H5N1 strain of Avian Influenza A virus or “bird flu” strain of influenza as well as the treatment or prophylaxis of Venezuela equine encephalitis virus or VEE.

  本发明涉及使用卡伯丁和5-F卡伯丁及其类似物用于治疗或预防流感，特别是禽流感A病毒的H5N1亚型或“禽流感”亚型以及治疗或预防委内瑞拉马蹄热病毒或VEE。
• Mukhopadhyay; Ghosh; De, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1999, vol. 38, # 9, p. 895 - 899
  作者：Mukhopadhyay、Ghosh、De

  DOI：——

  日期：——