9-(4-氯丁基)嘌呤-6-胺 | 69293-19-2

• 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: 9-(4-氯丁基)嘌呤-6-胺
• 英文名称: N⁹-(4-chlorobutyl)adenine
• 英文别名: 9-(4-chlorobutyl)-9H-purin-6-amine；9-(4-chlorobutyl)adenine；9-(4-chloro-butyl)-9H-purin-6-ylamine；9-(4-Chlor-butyl)-adenin；9-(4-chlorobutyl)purin-6-amine
• CAS: 69293-19-2
• 化学式: C₉H₁₂ClN₅
• 分子量: 225.681
• InChiKey: JOSMPXYVHRJDAU-UHFFFAOYSA-N

物化性质

• 沸点：
  448.0±55.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-(4-氯丁基)嘌呤-6-胺 在 sodium azide 、 四丁基溴化铵 作用下， 以 乙腈 为溶剂， 生成 9-(4-Azido-butyl)-9H-purin-6-ylamine
  参考文献：
  名称：

  On the binding site of quinolone antibacterials. An attempt to probe the shen model

  摘要：

  Quinolone-nucleic acid base hybrids were synthesized in an effort to probe a mechanistic model and a proposed mode of antibacterial action where stacked pairs of quinolones interact with DNA through H-bonding. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00430-1
• 作为产物：
  描述：

  9-(4-羟基丁基)腺嘌呤 在 氯化亚砜 作用下， 反应 3.0h， 以74.3%的产率得到9-(4-氯丁基)嘌呤-6-胺
  参考文献：
  名称：

  Pini; Rossi; Cornaglia Ferraris, Bollettino Chimico Farmaceutico, 2000, vol. 139, # 3, p. 107 - 113

  摘要：

  DOI：

文献信息

• [EN] HEMI-SYNTHETIC TRILOBINE ANALOGS FOR USE AS A DRUG<br/>[FR] ANALOGUES DE TRILOBINE SEMI-SYNTHÉTIQUES DESTINÉS À ÊTRE UTILISÉS COMME MÉDICAMENT
  申请人：PF MEDICAMENT

  公开号：WO2017055633A1

  公开（公告）日：2017-04-06

  The invention concerns a compound of the following formula (I) or a pharmaceutically acceptable salt or solvate thereof as well as a pharmaceutical composition containing such a compound, and the use of such a compound as a drug, notably as a DNMT inhibitor, in particular in the treatment of cancer.

  这项发明涉及以下式（I）的化合物或其药学上可接受的盐或溶剂，以及含有这种化合物的药物组合物，以及将这种化合物用作药物，特别是作为一种DNMT抑制剂，特别是在癌症治疗中的用途。
• Hemi-synthetic trilobine analogs for use as a drug
  申请人：PIERRE FABRE MEDICAMENT

  公开号：US10544156B2

  公开（公告）日：2020-01-28

  The invention concerns a compound of the following formula (I) or a pharmaceutically acceptable salt or solvate thereof as well as a pharmaceutical composition containing such a compound, and the use of such a compound as a drug, notably as a DNMT inhibitor, in particular in the treatment of cancer.

  本发明涉及下式 (I) 的化合物或其药学上可接受的盐或溶液，以及含有这种化合物的药物组合物，还涉及这种化合物作为药物的用途，特别是作为 DNMT 抑制剂，尤其是用于治疗癌症。
• X-ray crystallographic and two-dimensional NMR investigations of a coenzyme B12 analog with 5'-deoxyadenosine replaced by 9-(CH2)3-adenine
  作者：Thomas G. Pagano、Luigi G. Marzilli、Maria M. Flocco、Chao Tsai、H. L. Carrell、Jenny P. Glusker

  DOI：10.1021/ja00002a022

  日期：1991.1

  The structure of (adeninylpropyl)cobalamin (AdePrCbl), a coenzyme B12 ((5'-deoxyadenosyl)cobalamin) analogue in which the ribose moiety of the adenosyl group has been replaced by a propylene chain, has been determined by X-ray diffraction methods. AdePrCbl crystallizes in the orthorhombic space group P2(1)2(1)2(1), with Z = 4, a = 23.868 (9) angstrom, b = 21.027 (7) angstrom, c = 16.047 (4) angstrom, and v = 8053.07 angstrom3. The final R value is 0.100 based on 6621 observed reflections. The general conformations of the corrin ring, benzimidazole, phosphate, and ribose in AdePrCbl are very similar to those of (5'-deoxyadenosyl)cobalamin and methylcobalamin except for the amide side chains, which show some variability in the oriantations of their amide groups. The adenine ring in AdePrCbl lies over the D ring of the corrin system, rotated about 120-degrees clockwise from its position in coenzyme B-12. The ten water molecules in the crystal structure of AdePrCbl are well located and show no evidence of disorder. Complete H-1 and C-13 NMR assignments of AdePrCbl have been made by using the following two-dimensional NMR methods: homonuclear Hartmann-Hahn spectroscopy (HOHAHA), rotating frame Overhauser enhancement spectroscopy (ROESY), H-1-detected heteronuclear multiple-quantum-coherence (HMQC) spectroscopy, and H-1-detected multiple-bond heteronuclear multiple-quantum-coherence spectroscopy (HMBC). In addition to the adenine orientation found in the crystal structure, a second orientation, in which the adenine lies over the B ring of the corrin, is suggested by H-1 NOEs and by a comparison of the H-1 and C-13 shifts AdePrCbl to those of coenzyme B-12. Our results suggest that alkyladenine groups in cobalamins may have a highly fluxional character permitting several orientations of the adenine. Previous studies have shown that binding to the B-12-dependent enzymes ribonucleotide reductase and diol dehydrase is tighter for (adeninylpentyl)cobalamin than for coenzyme B-12 and the other (adeninylalkyl)cobalamins. On the basis of our studies, we conclude that the flexibility of the alkyl chain, exhibit by the fluxional character of the alkyladenine group, and the orientation of the adenine ring could be responsible for the increased affinity of this analogue for the enzyme. Difference in the orientation of the adenine and the fluxional character of the alkyladenine group, in addition to corrin ring flexibility, may also be useful in explaining the changes in the circular dichroism spectra of (adeninylalkyl)cobalamins upon binding to ethanolamine ammonia-lyase.
• HOLY, ANTONIN;ROSENBERG, IVAN;DVORAKOVA, HANA;DECLERCQ, ERIK, NUCLEOSIDES AND NUCLEOTIDES, 7,(1988) N-6, C. 667-670
  作者：HOLY, ANTONIN、ROSENBERG, IVAN、DVORAKOVA, HANA、DECLERCQ, ERIK

  DOI：——

  日期：——
• HEMI-SYNTHETIC TRILOBINE ANALOGS FOR USE AS A DRUG
  申请人：Pierre Fabre Médicament

  公开号：EP3355888A1

  公开（公告）日：2018-08-08