pvc增韧剂 | 90597-22-1

• 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
• 中文名称: pvc增韧剂
• 中文别名: 胞嘧啶杂质
• 英文名称: cyclopentenyl cytosine
• 英文别名: CPEC；4-amino-1-[(1R,4R,5S)-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl]pyrimidin-2-one
• CAS: 90597-22-1
• 化学式: C₁₀H₁₃N₃O₄
• 分子量: 239.231
• InChiKey: DUJGMZAICVPCBJ-VDAHYXPESA-N

物化性质

• 溶解度：
  Water 7.5 (mg/mL)
• 稳定性/保质期：
  Bulk: CPE-C was found to be stable under the following conditions: room temperature, dark; room temperature, light; 50 °C, dark; 50 °C, light. Solution: CPE-C was found to be stable at room temperature in 0.9% saline over a 75 hr period under exposure to light.
• 旋光度：
  (c = 0.3,0.1M phosphate buffer) [a]23D = -95 ± 5

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (+/-)-2,2-dimethyl-3αβ,6αβ-dihydro-4H-cyclopenta-1,3-dioxol-4-one 在 4-二甲氨基吡啶 、 双(乙腈)氯化钯(II) 、 potassium tert-butylate 、 氨 、 仲丁基锂 、 三乙胺 、 三苯基膦 、 三氟乙酸 、 对苯醌 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 108.5h， 生成 pvc增韧剂
  参考文献：
  名称：

  Enantiomeric Synthesis of d- and l-Cyclopentenyl Nucleosides and Their Antiviral Activity Against HIV and West Nile Virus

  摘要：

  Enantiomeric synthesis Of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus are described. The key intermediate (-)- and (+)-cyclopentenyl alcohols (7 and 15) were prepared from D-gamma -ribonolactone and D-ribose, respectively. Coupling of 7 with appropriately blocked purine and pyrimidine bases via the Mitsunobu reaction followed by deprotection afforded the target L-(+)-cyclopentenyl nucleosides (24-28, 31, 33, and 36). D-(-)Cyclopentenyl nucleosides (1, 40, 43, and 52-56) were also prepared by a similar procedure for L-isomers from 15. The synthesized compounds were evaluated for their antiviral activity against two RNA viruses: HIV and West Nile virus. Among the synthesized D-(-)-nucleosides, adenine (1, neplanocin A), cytosine (55, CPE-C), and 5-fluorocytosine (56) analogues exhibited moderate to potent anti-HIV activity (EC50 0.1, 0.06, and 5.34 muM, respectively) with significant cytotoxicity in PBM, Vero, and CEM cells. Also, cytosine (55) and 5-fluorocytosine (56) analogues exhibited the most potent anti-West Nile virus activity (EC50 0.2-3.0 and 15-20 muM, respectively). Among L-(+)-nucleosides, only the cytosine (27) analogue exhibited weak anti-HIV activity (EC50 58.9 muM).

  DOI：

  10.1021/jm010256v

文献信息

• Cyclopentenylcytosine. A carbocyclic nucleoside with antitumor and antiviral properties
  作者：Victor E. Marquez、Mu Ill Lim、Susan P. Treanor、Jacqueline Plowman、Matthew A. Priest、Anica Markovac、M. Sami Khan、Bashir Kaskar、John S. Driscoll

  DOI：10.1021/jm00117a004

  日期：1988.9

  Cyclopentenylcytosine (CPE-C, 2), a pyrimidine analogue of the fermentation derived carbocyclic nucleoside neplanocin A, has been synthesized from the optically active cyclopentenylamine 3b by two synthetic routes. CPE-C demonstrates significant antitumor activity against both the sensitive and ara-C resistant lines of L1210 leukemia in vivo. Multiple long term survivors are produced in both tumor

  环戊烯基胞嘧啶（CPE-C，2）是发酵衍生的碳环核苷内啡肽A的嘧啶类似物，它是通过光学合成的环戊烯基胺3b合成的。CPE-C在体内对L1210白血病的敏感株和ara-C耐药株均显示出显着的抗肿瘤活性。在两种肿瘤模型中均产生多个长期存活者。该化合物还对在无胸腺小鼠中生长的固体人A549肺和MX-1乳腺肿瘤异种移植物提供100％的生长抑制。还针对第三种人肿瘤异种移植模型转移性LOX黑色素瘤观察到良好的活性。CPE-C在体外对DNA和RNA病毒均具有显着活性。观察到针对HSV-1（TK +和TK-），HSV-2，牛痘，巨细胞病毒和水痘带状疱疹病毒的活性强。
• Antiviral and anticancer cyclopentenyl cytosine
  申请人：The United States of America as represented by the Secretary of the

  公开号：US04975434A1

  公开（公告）日：1990-12-04

  Cyclopentenyl pyrimidine compounds have potent anti-viral, anti-tumor and differentiating activity. Of these compounds, cyclopentenyl cytosine has proved to be particularly effective in a variety of tumors, as well as having good antiviral activity and potent differentiating properties.

  环戊烯基嘧啶化合物具有强大的抗病毒、抗肿瘤和分化作用。其中，环戊烯基胞嘧啶在多种肿瘤中被证明特别有效，同时具有良好的抗病毒活性和强大的分化特性。
• Compositions and methods for reducing neointima formation
  申请人：University of Georgia Research Foundation, Inc.

  公开号：US10328182B2

  公开（公告）日：2019-06-25

  Compositions, devices, grafts and methods for reducing or preventing anti-neointima following cardiovascular injuries and interventions are disclosed. The compositions, devices, and grafts typically include an effective amount of a CTP synthase 1 inhibitor to reduce proliferation of vascular smooth muscle cells, without substantial reducing the proliferation of endothelial cells. Methods of reducing neointima formation, accelerating re-endothelialization, and reducing restenosis in a subject using the compositions, devices, and grafts are also disclosed.

  本研究公开了用于减少或预防心血管损伤和干预后的抗新生血管的组合物、装置、移植物和方法。这些组合物、装置和移植物通常包括有效量的 CTP 合酶 1 抑制剂，以减少血管平滑肌细胞的增殖，而不会大量减少内皮细胞的增殖。此外，还公开了使用这些组合物、装置和移植物减少新内膜形成、加速再内皮化和减少受试者再狭窄的方法。
• Enantioselective synthesis of new analogs of neplanocin A and their biological activity
  作者：Masafumi Arita、Takeki Okumoto、Tadamasa Saito、Yukio Hoshino、Kiyofumi Fukukawa、Satoshi Shuto、Masatoshi Tsujino、Hideo Sakakibara、Masaji Ohno

  DOI：10.1016/s0008-6215(00)90890-5

  日期：1987.12
• Cyclopentenyluridine and cyclopentenylcytidine analogs as inhibitors of uridine-cytidine kinase
  作者：Mu Ill Lim、James D. Moyer、Richard L. Cysyk、Victor E. Marquez

  DOI：10.1021/jm00378a002

  日期：1984.12