6-propylaminopurine | 16370-58-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 6-propylaminopurine
• 英文别名: N6-propyladenine；6-Propylamino-purin；N-propyl-7H-purin-6-amine
• CAS: 16370-58-4
• 化学式: C₈H₁₁N₅
• mdl: MFCD04457471
• 分子量: 177.209
• InChiKey: CIAUYDNALIJKPK-UHFFFAOYSA-N

物化性质

• 沸点：
  284.9±50.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-propylaminopurine 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.75h， 生成 6-[6-(propylamino)purin-9-yl]hexyl (5R,6S,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylate
  参考文献：
  名称：

  Lignopurines: A new family of hybrids between cyclolignans and purines. Synthesis and biological evaluation

  摘要：

  A new family of hybrids between cyclolignans related to podophyllic aldehyde, a non-lactonic cyclolignan, and purines were prepared and evaluated against several human tumour cell lines. Both fragments, cyclolignan and purine, were linked through aliphatic and aromatic chains. The influence on the cytotoxicity of the purine substitution and the nature of the linker is analyzed. The new family was slightly less cytotoxic than the parent podophyllic aldehyde, although the selectivity is maintained or even improved and among the linkers used, the presence of an aromatic ring gave the most potent and selective derivatives within the new series tested. Cell cycle and confocal studies demonstrate that these derivatives interfere with the tubulin polymerization and arrest cells at the G(2)/M phase, in the same way than the parent compounds podophyllotoxin and podophyllic aldehyde do. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.026
• 作为产物：
  描述：

  6-氯嘌呤 在 正丙胺 作用下， 生成 6-propylaminopurine
  参考文献：
  名称：

  Process for preparing N6,9-disubstituted adenine

  摘要：

  一种制备N.sup.6, 9-二取代腺嘌呤的方法，包括将N.sup.6-取代腺嘌呤的金属盐与苄卤化合物反应，最好在相转移催化剂的存在下进行。根据该方法，可以高产率和良好选择性地得到N.sup.6,9-二取代腺嘌呤。

  公开号：

  US04900826A1

文献信息

• Convenient and Efficient Syntheses of<i>N</i>⁶- and<i>N</i>⁴- Substituted Adenines and Cytosines and their 2′-Deoxyribosides
  作者：Ewelina Adamska、Jan Barciszewski、Wojciech T. Markiewicz

  DOI：10.1080/15257770.2012.742198

  日期：2012.12

  Convenient and efficient methods of the synthesis of N6- and N4-substituted derivatives of adenine and cytosine and their 2′-deoxyribosides were developed. The reactions of either unprotected nucleobases (adenine, cytosine) or unprotected 2′-deoxyribosides with aryl or alkyl aldehydes give corresponding Schiff bases that can be reduced to the target title compounds with high overall yields. In the

  开发了一种便捷高效的合成腺嘌呤和胞嘧啶的N 6-和N 4-取代衍生物及其2'-脱氧核糖苷的方法。未保护的核碱基（腺嘌呤，胞嘧啶）或未保护的2'-脱氧核糖苷与芳基或烷基醛的反应可生成相应的席夫碱，这些席夫碱可被还原为目标标题化合物，且总收率高。在芳基醛的情况下，亚胺衍生物在甲醇中的甲醇盐存在下获得，并用硼氢化钠还原。与烷基醛的相应反应需要使用乙酸和硼烷二甲基硫醚络合物。
• [EN] SMALL MOLECULE INHIBITORS OF AUTOPHAGY AND HISTONE DEACTYLASES AND USES THEREOF<br/>[FR] INHIBITEURS À PETITES MOLÉCULES D'AUTOPHAGIE ET D'HISTONE DÉSACÉTYLASE ET LEURS UTILISATIONS
  申请人：UNIV ARIZONA

  公开号：WO2021087077A1

  公开（公告）日：2021-05-06

  This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having a quinoline or thioxanthenone (or similar) structure which function as autophagy inhibitors and/or histone deactylase inhibitors, and their use as therapeutics for the treatment of conditions characterized with aberrant autophagy activity and/or aberrant HDAC activity (e.g., cancer, pulmonary hypertension, diabetes, neurodegenerative disorders, aging, heart disease, rheumatoid arthritis, infectious diseases, conditions and symptoms caused by a viral infection (e.g., COVID-19)).

  这项发明属于药物化学领域。特别是，该发明涉及一类新的小分子，具有喹啉或噻吨酮（或类似）结构，可作为自噬抑制剂和/或组蛋白脱乙酰酶抑制剂发挥作用，并用作治疗以异常自噬活性 和/或异常HDAC活性（例如，癌症、肺动脉高压、糖尿病、神经退行性疾病、衰老、心脏病、类风湿性关节炎、感染性疾病、病毒感染（例如，COVID-19）引起的状况和症状）为特征的疾病的治疗方法。
• Method for treating disease or condition susceptible to amelioration by AMPK activators and compounds of formula which are useful to activate AMP-activated protein kinase (AMPK)
  申请人：CHEN Han-Min

  公开号：US20140303112A1

  公开（公告）日：2014-10-09

  The present invention relates to a method for treating disease or condition susceptible to amelioration by AMPK activators and compounds of formula which are useful to activate AMP-activated protein kinase (AMPK) and the use of the compounds in the prevention or treatment of disease, including pre-diabetes, type 2 diabetes, syndrome X, metabolic syndrome and obesity.

  本发明涉及一种治疗疾病或病情的方法，该疾病或病情容易通过AMPK激活剂和公式化合物得到改善，这些化合物有助于激活AMP激活蛋白激酶（AMPK），并将这些化合物用于预防或治疗疾病，包括糖尿病前期、2型糖尿病、X综合症、代谢综合征和肥胖症。
• Bio-catalytic synthesis of unnatural nucleosides possessing a large functional group such as a fluorescent molecule by purine nucleoside phosphorylase
  作者：Akihiko Hatano、Hiroyuki Wakana、Nanae Terado、Aoi Kojima、Chisato Nishioka、Yu Iizuka、Takuya Imaizumi、Sanae Uehara

  DOI：10.1039/c9cy01063g

  日期：——

  large functional fluorescent group, 5-(coumarin-7-oxyhex-5-yn) uracil (C4U). Conversion to 2′-deoxy-[5-(coumarin-7-oxyhex-5-yn)] uridine (dRC4U) was drastically enhanced by DMSO addition. Docking simulations between dRC4U and E. coli PNP (PDB 3UT6) showed the uracil moiety in the active-site pocket of PNP with the fluorescent moiety at the entrance of the pocket. Thus, the bulky fluorescent moiety has little

  非天然核苷作为潜在的诊断工具，药物和功能分子引起了人们的兴趣。然而，难以以高收率和β-区域选择性将非天然核碱基偶联至核糖的1'-位置。嘌呤核苷磷酸化酶（PNP，EC2.4.2.1）是一种代谢酶，可在磷酸缓冲液中以100％α-选择性催化肌苷向核糖-1α-磷酸和游离次黄嘌呤的转化。我们探讨了PNP是否可用于合成非天然核苷。PNP催化作为核糖供体的胸腺嘧啶核苷与嘌呤的反应生成2'-deoxynebularine（3，β形式）的转化率很高（80％）。它还催化胸腺嘧啶的磷酸化，并以中等产率（52-73％）将核苷的5-位被卤素原子取代的嘧啶碱基引入核糖的1'-位，表明它显示出较弱的选择性。对于庞大的嘌呤底物[例如6-（N，N，N-二丙基氨基）]，产率较低，但是添加极性溶剂例如二甲基亚砜（DMSO）将产率提高至74％。PNP还催化胸腺嘧啶与具有较大功能性荧光基团的尿嘧啶（5-香豆素-7-oxyhex-5
• NUCLEOTIDE DERIVATIVE OR SALT THEREOF, NUCLEOTIDE-DERIVED 5'-PHOSPHATE ESTER OR SALT THEREOF, NUCLEOTIDE-DERIVED 3'-PHOSPHORAMIDITE COMPOUND OR SALT THEREOF, AND POLYNUCLEOTIDE
  申请人：NATIONAL UNIVERSITY CORPORATION GUNMA UNIVERSITY

  公开号：US20160311845A1

  公开（公告）日：2016-10-27

  A nucleoside derivative represented by any of the following formulae (I-1) to (I-6) or a salt thereof: in the formulae (I-1) to (I-6), R 1 to R 5 , A 1 to A 3 , B, X, Y, and k represent the meanings as described in claim 1.

  由以下任一式(I-1)至(I-6)或其盐所表示的核苷衍生物：在式(I-1)至(I-6)中，R1至R5、A1至A3、B、X、Y和k代表如权利要求书中所述的含义。