3-(6-氨基-嘌呤-9-基)-丙烷-1-醇 | 711-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 3-(6-氨基-嘌呤-9-基)-丙烷-1-醇
• 英文名称: 9-(3-hydroxypropyl)adenine
• 英文别名: 3-(6-Amino-9H-purin-9-yl)propan-1-ol；3-(6-aminopurin-9-yl)propan-1-ol
• CAS: 711-64-8
• 化学式: C₈H₁₁N₅O
• 分子量: 193.208
• InChiKey: BLZBVHFRNUTFCH-UHFFFAOYSA-N

物化性质

• 熔点：
  218-220 °C
• 沸点：
  482.7±55.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(6-氨基-嘌呤-9-基)-丙烷-1-醇 生成 3-(adenin-9-yl)propanal
  参考文献：
  名称：

  ROSENBERG, IVAN;HOLY, ANTONIN;MASOJIDKOVA, MILENA, COLLECT. CZECHOSL. CHEM. COMMUN., 53,(1988) N1B, C. P2753-2777

  摘要：

  DOI：
• 作为产物：
  描述：

  腺嘌呤 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 3-(6-氨基-嘌呤-9-基)-丙烷-1-醇
  参考文献：
  名称：

  Holy, Antonin; Kohoutova, Jitka; Merta, Ales, Collection of Czechoslovak Chemical Communications, 1986, vol. 51, # 2, p. 459 - 477

  摘要：

  DOI：

文献信息

• 8-(2-Furyl)adenine derivatives as A2A adenosine receptor ligands
  作者：Diego Dal Ben、Michela Buccioni、Catia Lambertucci、Ajiroghene Thomas、Karl-Norbert Klotz、Stephanie Federico、Barbara Cacciari、Giampiero Spalluto、Rosaria Volpini

  DOI：10.1016/j.ejmech.2013.10.006

  日期：2013.12

  8-(2-furyl)adenine derivatives are reported. Results show that 8-(2-furyl)-9-methyladenine is endowed with high affinity at the A2A subtype. Further modification of this compound with introduction of arylacetyl or arylcarbamoyl groups in N6-position takes to different effects on the A2A affinity and in particular on the selectivity versus the other three adenosine receptor subtypes. A molecular modelling

  选择性腺苷受体调节剂是用于许多治疗应用的潜在工具，包括心血管，炎性和神经退行性疾病。在这项工作中，报道了一系列9-取代的8-（2-呋喃基）腺嘌呤衍生物的四种人腺苷受体亚型的合成和生物学评估。结果表明8-（2-呋喃基）-9-甲基腺嘌呤在A 2A亚型上具有高亲和力。通过在N 6位上引入芳基乙酰基或芳基氨基甲酰基基团对该化合物进行进一步修饰，对A 2A亲和力，特别是相对于其他三种腺苷受体亚型，对选择性具有不同的影响。三种不同的A 2A下的分子建模分析 受体晶体结构提供了对所获得的生物学结果的解释。
• Intramolecular Cyclization of Some Acyclic Nucleoside Analogs
  作者：Zlatko Janeba、Antonín Holý、Hana Votavová、Milena Masojídková

  DOI：10.1135/cccc19960442

  日期：——

  Reaction of stereoisomeric 8-bromo-9-(2,3-O-isopropylidene-2,3,4-trihydroxybutyl)adenines (8) with concentrated aqueous ammonia, sodium hydride, potassium tert-butoxide, or 1,8-diazabicyclo[5,4,0]undec-7-ene afforded 4e-O,8-anhydro-9-(2,3-O-isopropylidene-2,3,4-trihydroxybutyl)adenines 9 (derivatives of 1,3-oxazepino[2,3-e]adenine). The CD spectra of optically active stereoisomers of 9 have been studied and it was found that for threo isomers 9a and 9b their character corresponds to 5'-O,8-cycloadenosine. The compounds 9 were also prepared by oxidative cyclization of 9-(2,3-O-isopropylidene-2,3,4-trihydroxybutyl)adenines (7) with lead(IV) acetate in benzene. Reaction of 9-(4-hydroxybutyl)adenine (14) with lead(IV) acetate smoothly afforded the seven-membered ring derivative, 4'-O,8-anhydro-9-(4-hydroxybutyl)adenine (15); no anhydro products with five-, six-, and eight-membered ring were found. 2',3'-O-Isopropylideneinosine (16) reacted with lead(IV) acetate to give 5'-O,8-cyclo-2',3'-O-isopropylideneinosine (17) whereas 9-(4-hydroxybutyl)hypoxanthine (18) afforded no cyclic products.

  立体异构体8-溴-9-(2,3-O-异丙基-2,3,4-三羟基丁基)腺嘌呤（8）与浓氨水、氢化钠、叔丁醇钾或1,8-二氮杂双环[5,4,0]十一烯反应，得到4e-O,8-去水-9-(2,3-O-异丙基-2,3,4-三羟基丁基)腺嘌呤9（1,3-噁唑并[2,3-e]腺嘌呤的衍生物）。对9的光学活性立体异构体的CD光谱进行了研究，发现对于threo异构体9a和9b，它们的特征对应于5'-O,8-环腺苷。化合物9也可以通过9-(2,3-O-异丙基-2,3,4-三羟基丁基)腺嘌呤（7）与醋酸铅（IV）在苯中氧化环化制备而成。9-(4-羟基丁基)腺嘌呤（14）与醋酸铅（IV）反应顺利地得到七元环衍生物4'-O,8-去水-9-(4-羟基丁基)腺嘌呤（15）；没有发现五元、六元和八元环的去水产物。2',3'-O-异丙基核苷（16）与醋酸铅（IV）反应，得到5'-O,8-环-2',3'-O-异丙基核苷（17），而9-(4-羟基丁基)次黄嘌呤（18）没有产生环状产物。
• Synthesis Method For Improved Tenofovir Disoproxil Fumarate Using Ion-Exchange Resin And Method For Preparing Oral Dissolving Film Form Using The Same
  申请人：FIRSON

  公开号：US20170354668A1

  公开（公告）日：2017-12-14

  The present invention relates to a synthesis method of preventing the formation of impurities and byproducts in the synthesis of tenofovir disoproxil fumarate (Teno-DF) used as a medicine for hepatitis B and HIV treatment due to its function to promote bioactivities. In the synthesis method of the present invention, an ion-exchange resin (Dowex 50W hydrogen form, sulfonic acidic cation exchange resin) is used to enhance the yield and purity of the compound. The present invention also relates to a method of preparing an oral dissolving film dosage form in the manufacture of a medicine using the tenofovir compound with high purity obtained by the synthesis method of the present invention as an effective ingredient.

  本发明涉及一种合成方法，用于预防在合成用于治疗乙肝和艾滋病的替诺福韦二丙氧基富马酸盐（Teno-DF）的过程中形成杂质和副产物的方法。该化合物因其促进生物活性的功能而被用作药物。在本发明的合成方法中，使用一种离子交换树脂（Dowex 50W氢型，磺酸性阳离子交换树脂）来增强化合物的产率和纯度。本发明还涉及一种制备口溶膜剂型的方法，用于制造药物，使用本发明的合成方法获得的高纯度替诺福韦化合物作为有效成分。
• Orally Active Purine-Based Inhibitors of Heat Shock Protein 90
  申请人：Kasibhatla R. Srinivas

  公开号：US20070129334A1

  公开（公告）日：2007-06-07

  Novel purine compounds and tautomers and pharmaceutically acceptable salts thereof are described, as are pharmaceutical compositions comprising the same, complexes comprising the same, e.g., HSP90 complexes, and methods of using the same. Methods of using the novel purine compounds of the invention, and tautomers and pharmaceutically acceptable salts thereof, include their use in inhibiting heat shock protein 90's (HSP90's) to thereby treat or prevent HSP90-dependent diseases, e.g., proliferative disorders such as breast cancer.

  本发明描述了新型嘌呤化合物及其互变异构体和药学上可接受的盐，以及包含它们的制药组合物、包含它们的复合物（例如HSP90复合物）和使用它们的方法。使用本发明的新型嘌呤化合物、互变异构体和药学上可接受的盐的方法包括在抑制热休克蛋白90（HSP90）中使用它们，从而治疗或预防HSP90依赖性疾病，例如增生性疾病如乳腺癌。
• Advanced drug development and manufacturing
  申请人：Los Alamos National Security, LLC

  公开号：EP2511844A2

  公开（公告）日：2012-10-17

  There is described an apparatus for measuring protein characteristics comprising an X-ray fluorescence (XRF) spectrometer comprising a source of polychromatic X-rays, an X-ray detector, a protein, a molecule that has been exposed to and at least weakly binds to the protein, a plurality of X-ray fluorescence signal data obtained by irradiating chemical elements in the protein and molecule with the polychromatic X-rays and a security system for maintaining records for the data from the plurality of X-ray fluorescence signal measurements. There is also described an x-ray microscope for measuring a sample.

  描述了一种测量蛋白质特性的仪器，该仪器包括一个 X 射线荧光 (XRF) 光谱仪，其中包括一个多色 X 射线源、一个 X 射线探测器、一个蛋白质、一个已暴露于该蛋白质并至少与该蛋白质弱结合的分子、通过用多色 X 射线照射蛋白质和分子中的化学元素而获得的多个 X 射线荧光信号数据，以及一个用于维护多个 X 射线荧光信号测量数据记录的安全系统。此外，还介绍了一种用于测量样品的 X 射线显微镜。