(1S,2S,3S,5S)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol | 69979-44-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,3S,5S)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol
• CAS: 69979-44-8
• 化学式: C₆H₁₃NO₃
• 分子量: 147.174
• InChiKey: FHNKBDPGQXLKRW-BXKVDMCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S,5S)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol 在 盐酸 、 sodium acetate 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 乙醇 、 水 、 溶剂黄146 、 正丁醇 为溶剂， 反应 86.0h， 生成 (+/-)-5-amino-7-hydroxy-3-<2α,3β-dihydroxy-4α-(hydroxymethyl)cyclopent-1α-yl>-ν-triazolo<4,5-d>pyrimidine
  参考文献：
  名称：

  阿拉伯糖嘌呤核苷的碳环类似物

  摘要：

  阿拉伯呋喃糖基鸟嘌呤（VII）和2,6-二氨基-9-β-阿拉伯呋喃糖基嘌呤（VIII）的碳环类似物和相应的8-氮杂嘌呤类似物5-氨基-7-羟基-3- [2α，3β-二羟基-4 α-（羟甲基）环戊-1α-基] -v-三唑并[4,5-d]嘧啶（X）和5,7-二氨基-3- [2 alpha，3β-二羟基-4α-（羟甲基）制备）环戊-1α-基] -v-三唑并[4，5-d]嘧啶（XI）。碳环核苷类似物VII和X对培养的P-388小鼠白血病细胞表现出明显的细胞毒性。针对1型单纯疱疹（HF株）的体外测试表明，只有VIII表现出显着的抗病毒活性。

  DOI：

  10.1002/jps.2600690910
• 作为产物：
  描述：

  (1R,4S)-4-Acetylamino-cyclopent-2-enecarboxylic acid 在 吡啶 、 盐酸 、 calcium borohydride 、 硫酸 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 65.0h， 生成 (1S,2S,3S,5S)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol
  参考文献：
  名称：

  Katagiri, Nobuya; Kokufuda, Hideaki; Makino, Masashi, Nucleosides and Nucleotides, 1998, vol. 17, # 1-3, p. 81 - 89

  摘要：

  DOI：

文献信息

• 2-Azabicyclo[2.2.1]hept-5-en-3-one epoxide: A versatile intermediate for the synthesis of cyclopentyl carbocyclic 2-deoxy-, 3-deoxy- &amp; ara- ribonucleoside analogues
  作者：Belén M Domínguez、Paul M Cullis

  DOI：10.1016/s0040-4039(99)01113-2

  日期：1999.7

  5,6-Epoxy-exo-2-azabicyclo[2.2.1]heptan-3-one has been used as a versatile intermediate in the synthesis of 2-deoxy-, 3-deoxy- and ara- cyclopentyl carbocyclic nucleosides. An efficient, short synthesis of the (+) carbocyclic thymidine 13 is reported.

  5，6-环氧-外-2--2-氮杂双环[2.2.1]庚-3-已被用作合成2-脱氧，3-脱氧和芳基-环戊基碳环核苷的通用中间体。报道了（+）碳环胸苷13的有效的，短的合成。
• C-2 Arylamino substituted purine<i>ara</i>-carbocyclic nucleosides as potential anti-cytomegalovirus agents
  作者：Masakazu Koga、Stewart W. Schneller

  DOI：10.1002/jhet.5570290711

  日期：1992.12

  that placement of an arylamino side chain at the C-2 position of purine nucleosides produces compounds capable of inhibiting DNA polymerase. To evaluate the potential of this class of compounds as antiviral agents that act by inhibiting viral DNA polymerase, ara-carbocyclic purine nucleosides possessing a 4-(l-butyl)phenylamino and a 3,5-dichlorophenylamino substituent at C-2 were chosen as the prototype

  文献中有报道，在嘌呤核苷的C-2位上放置芳基氨基侧链会产生能够抑制DNA聚合酶的化合物。为了评估这种类作为抗病毒剂通过抑制病毒DNA聚合酶的行为，化合物的潜在ARA在C-2具有一个4-（1-丁基）苯基氨基和3,5-二氯苯基取代基-碳环嘌呤核苷被选为由2,4,6-三氯嘧啶分6步制备。对于抗病毒分析，人巨细胞病毒是主要病毒，因为它表达病毒特异性DNA聚合酶。这些化合物均未显示出对该病毒的活性，但发现它们对一种或多种细胞系显示出一定的毒性。
• Carbocyclic analogs of xylofuranosylpurine nucleosides. Synthesis and antitumor activity
  作者：Robert Vince、Jay Brownell、Susan Daluge

  DOI：10.1021/jm00376a025

  日期：1984.10

  xylofuranosyladenine and xylofuranosyl-8-azaadenine were prepared. In contrast to 9-beta-D-xylofuranosyladenine and its 8-aza analogue, the corresponding carbocyclic nucleosides were resistant to deamination by adenosine deaminase. The carbocyclic 8-aza derivative 10 exhibited significant in vivo antitumor activity which varied according to treatment schedule.

  （+/-）-4 alpha-Amino-2 alpha，3 beta-dihydroxy-1 alpha-cyclopentanemethanol（6）是木呋喃糖胺的碳环类似物，是由先前报道的4 alpha-acetamido-2 alpha，3 alpha-合成的环氧环戊烷-1α-甲醇。通过与5缩合将胺6转化为（+/-）-4α-[（5-氨基-6-氯-4-嘧啶基）氨基] -2α，3β-二羟基-1α-环戊烷甲醇（7） -氨基-4，6-二氯嘧啶。从7，制备了木呋喃糖基腺嘌呤和木呋喃糖基-8-氮杂腺嘌呤的碳环类似物。与9-β-D-木呋喃糖基腺嘌呤及其8-氮杂类似物相反，相应的碳环核苷对腺苷脱氨酶具有抗脱氨性。碳环8-氮杂衍生物10显示出显着的体内抗肿瘤活性，其根据治疗方案而变化。
• A New Route to 2,5-Diamino-4,6-dichloropyrimidine, A Key Precursor of 9-Substituted Guanines
  作者：Michel Legraverend、Hassane Boumchita、Emile Bisagni

  DOI：10.1055/s-1990-26949

  日期：——

  An improved synthesis of 2,5-diamino-4,6-dihydroxypyrimidine (7) is reported. The direct chlorination of 7 provides the shortest (2 step) synthesis of 2,5-diamino-4,6-dichloropyrimidine (5) reported to date. The procedure described here affords an easy approach to 5, a key intermediate to various 9-substituted guanines.

  报告了2,5-二氨基-4,6-二羟基嘧啶（7）的改进合成方法。7的直接氯化提供了迄今为止报道的2,5-二氨基-4,6-二氯嘧啶（5）的最短（2步）合成方法。这里描述的方法为5（各种9-取代鸟嘌呤的关键中间体）提供了简便的方法。
• (.+-.)-2-Amino-3,4-dihydro-7-[2,3-dihydroxy-4-(hydroxymethyl)-1-cyclopentyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ones: new carbocyclic analogs of 7-deazaguanosine with antiviral activity
  作者：Michel Legraverend、Rose Marie Nia Ngongo-Tekam、Emile Bisagni、Aurelio Zerial

  DOI：10.1021/jm00148a017

  日期：1985.10

  5-Allyl-2-amino-4,6-dihydroxypyrimidine (3) was chlorinated and ozonized to yield (2-amino-4,6-dichloro-pyrimidin-5-yl)acetaldehyde (5). Acetalization of 5 with ethanol afforded a new pyrimidine intermediate 6 which can lead to 2-amino-3,4-dihydro-7-alkyl-7H-pyrrolo[2,3-d]pyrimidin-4-ones and therefore to carbocyclic analogues of 7-deazaguanosine. The 7-substituent was a cyclopentyl analogue of the arabinofuranosyl moiety in 10a, lyxofuranosyl moiety in 10b, and ribofuranosyl moiety in 10c. Compounds 10a and 10b exhibited selective inhibitory activities against the multiplication of HSV1 and HSV2 in cell culture. Repeated administration of compound 10a at 10mg/kg ip to mice infected with HSV2 increased the number of survivors and lengthened significantly the mean survival time.