(+/-)-9-<4'β,5'α-bis(hydroxymethyl)cyclopent-2'-en-1'β-yl>adenine | 140440-40-0

• 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: (+/-)-9-<4'β,5'α-bis(hydroxymethyl)cyclopent-2'-en-1'β-yl>adenine
• 英文别名: (+/-)-9--9H-adenine；9--9H-adenine；9-(c-4, t-5-bishydroxymethylcyclopent-2-en-r-1-yl)-9H-adenine；[(1S,4R,5R)-4-(6-aminopurin-9-yl)-5-(hydroxymethyl)cyclopent-2-en-1-yl]methanol
• CAS: 140440-40-0
• 化学式: C₁₂H₁₅N₅O₂
• 分子量: 261.283
• InChiKey: ZGCLIXGLQFSZRB-IWSPIJDZSA-N

物化性质

• 沸点：
  556.2±60.0 °C(Predicted)
• 密度：
  1.66±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-9-<4'β,5'α-bis(hydroxymethyl)cyclopent-2'-en-1'β-yl>adenine 在 phosphate buffer 、 adenosine deaminase 作用下， 生成 (1R,4S,5R)-9-<4,5-bis(hydroxymethyl)cyclopent-2-en-1-yl>-1H,9H-hypoxanthine
  参考文献：
  名称：

  Synthesis of Nucleosides and Related Compounds. XXXI. Resolution of 9-(c-4, t-5-Bis(hydroxymethyl)cyclopent-2-en-r-1-yl)-9H-adenine ((.+-.)-BCA) by Means of High-Pressure-Mediated Deamination with Adenosine Deaminase.

  摘要：

  研究了在各种压力（1 bar-6 kbar）下，抗人类免疫缺陷病毒（抗HIV）碳环腺嘌呤核苷9-[c-4, t-5-双（羟甲基）环戊-2-烯-r-1-基]-9H-腺嘌呤（BCA）的脱氨作用。 研究发现，虽然（+）-BCA几乎没有受到影响，但在4 kbar的压力下，对（-）-BCA的脱氨作用显著增强，产生了相应的（-）-次黄嘌呤衍生物（（-）-BCH），ee值接近100%。

  DOI：

  10.1248/cpb.41.1027
• 作为产物：
  描述：

  7-syn-<(benzyloxy)methyl>-2-azabicyclo<2.2.1>hept-5-en-3-one 在 盐酸 、 氢氧化钾 、 sodium tetrahydroborate 、 氨 、 三氯化硼 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 117.0h， 生成 (+/-)-9-<4'β,5'α-bis(hydroxymethyl)cyclopent-2'-en-1'β-yl>adenine
  参考文献：
  名称：

  Synthesis and anti-HIV activity of 9-[c-4,t-5-bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine

  摘要：

  The synthesis and in vitro anti-HIV activity of two new racemic nucleoside analogues are described; namely, 9-[c-4,t-5-bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine (12) and its guanine analogue 18. While the latter (18) showed no activity, the therapeutic index of the former (12) was 200 and comparable to that (400) of carbovir. One enantiomer of 12 may be viewed as an analogue of carbocyclic oxetanocin and the other as an analogue of carbovir. Hence, these results indicate that one or both of the individual enantiomers of 12 could serve as candidates or lead compounds for the development of anti-AIDS agents.

  DOI：

  10.1021/jm00088a026

文献信息

• Chemoenzymatic Synthesis of Antiviral Carbocyclic Nucleosides:  Asymmetric Hydrolysis of <i>meso</i>-3,5-Bis(acetoxymethyl)cyclopentenes Using <i>Rhizopus </i><i>delemar</i> Lipase
  作者：Masakazu Tanaka、Yoshihiko Norimine、Toshiaki Fujita、Hiroshi Suemune、Kiyoshi Sakai

  DOI：10.1021/jo9608230

  日期：1996.1.1

  norbornadienes were stereoselectively converted into the meso-3,5-bis(acetoxymethyl)cyclopentenes by a three-step sequence of ozonolysis, reduction, and acetylation. Rhizopus delemar lipase (RDL)-catalyzed asymmetric hydrolysis of meso-3,5-bis(acetoxymethyl)cyclopentenes afforded the monoalcohols of high enantiomeric purities (>95% ee) in good yields (64-95%). The obtained monoalcohols 11 and 14 could be

  通过三步的臭氧分解，还原和乙酰化反应，将7位取代的降冰片二烯立体选择性地转化为内消旋3,5-双（乙酰氧基甲基）环戊烯。根瘤菌脂肪酶（RDL）催化的内消旋3,5-双（乙酰氧基甲基）环戊烯不对称水解可提供高对映体纯度（> 95％ee）的一元醇，收率良好（64-95％）。所得一元醇11和14可用于合成抗病毒碳环核苷（-）-carbovir和（-）-BCA。
• Synthesis of (1R, 4S, 5R)-9-(4,5-bishydroxy-methylcyclopent-2-en-1-yl)-9H-adenine [(-)-BCA] and selective inhibition of human immunodeficiency virus
  作者：Nobuya Katagiri、Akemi Toyota、Takuya Shiraishi、Hiroshi Sato、Chikara Kaneko

  DOI：10.1016/s0040-4039(00)92675-3

  日期：1992.6

  (1R,4S,5R)-9-(4,5-Bishydroxymethylcyclopent-2-en-1-yl)-9H-adenine [(-)-BCA] has been synthesized from (-)-Corey lactone in 11 steps and shown to have potent and selective effects against human immunodeficiency virus type 1. The result demonstrated that the potent-HIV activity of racemic BCA obtained in our previous work is expressed solely by the (1R,4S,5R)-(-)-isomer.

  (1R,4S,5R)-9-(4,5-双羟甲基环戊-2-烯-1-基)-9H-腺嘌呤 [(-)-BCA] 从 (-)-科里内酯出发，经过11步反应合成，并显示出对人类免疫缺陷病毒1型的强效和选择性抑制作用。结果显示，在我们之前工作中获得的消旋BCA的强效抗HIV活性仅由 (1R,4S,5R)-(-)-异构体表达。
• Explanation for Stereoselectivity of the cis-Dihydroxylation of cis-3,5-disubstituted Cyclopentenes.
  作者：Nobuya KATAGIRI、Yumiko ITO、Kenji KITANO、Akemi TOYOTA、Chikara KANEKO

  DOI：10.1248/cpb.42.2653

  日期：——

  Stereoselectivity of the cis-dihydroxylation of cis-3, 5-disubstituted cyclopentenes has been found to depend on the conformation of cyclopenetenes and has been explained by both steric and Cieplak effects.

  研究发现，顺式-3, 5-二取代环戊烯的顺式二羟基化的立体选择性取决于环戊烯的构象，并可通过立体效应和 Cieplak 效应加以解释。
• Katagiri, Nobuya; Sato, Hiroshi; Arai, Sachie, Heterocycles, 1992, vol. 34, # 6, p. 1097 - 1100
  作者：Katagiri, Nobuya、Sato, Hiroshi、Arai, Sachie、Toyota, Akemi、Kaneko, Chikara

  DOI：——

  日期：——
• Synthesis and anti-HIV activity of 9-[c-4,t-5-bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine
  作者：Nobuya Katagiri、Masahiro Nomura、Hiroshi Sato、Chikara Kaneko、Keisuke Yusa、Takashi Tsuruo

  DOI：10.1021/jm00088a026

  日期：1992.5

  The synthesis and in vitro anti-HIV activity of two new racemic nucleoside analogues are described; namely, 9-[c-4,t-5-bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine (12) and its guanine analogue 18. While the latter (18) showed no activity, the therapeutic index of the former (12) was 200 and comparable to that (400) of carbovir. One enantiomer of 12 may be viewed as an analogue of carbocyclic oxetanocin and the other as an analogue of carbovir. Hence, these results indicate that one or both of the individual enantiomers of 12 could serve as candidates or lead compounds for the development of anti-AIDS agents.