2-chloro-N6-(5-methylfurfuryl)adenine | 1133758-66-3

• 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: 2-chloro-N6-(5-methylfurfuryl)adenine
• 英文别名: 2-chloro-6-(5-methylfurfurylamino)purine；2-chloro-N-[(5-methyl-2-furyl)methyl]-9H-purin-6-amine；2-chloro-N-[(5-methylfuran-2-yl)methyl]-7H-purin-6-amine
• CAS: 1133758-66-3
• 化学式: C₁₁H₁₀ClN₅O
• mdl: MFCD27271094
• 分子量: 263.686
• InChiKey: ABAUGIZWACETCO-UHFFFAOYSA-N

物化性质

• 密度：
  1.526±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  79.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  zinc(II) chloride dihydrate 、 2-chloro-N6-(5-methylfurfuryl)adenine 以 甲醇 为溶剂， 以39%的产率得到[zinc(II)(2-chloro-N6-(5-methylfurfuryl)adenine)2dichloride]
  参考文献：
  名称：

  Synthesis and characterization of the first zinc(II) complexes involving kinetin and its derivatives: X-ray structures of 2-chloro-N6-furfuryl-9-isopropyladenine and [Zn(kinetin)2Cl2]·CH3OH

  摘要：

  A series of the first zinc(II) complexes of the general composition [Zn(L-n)(2)Cl-2]center dot xSolv (1-5) involving kinetin [N6-furfuryladenine, L-1, xSolv = CH3OH, complex 1] and its derivatives, i.e. N6-(5-methylfurfuryl)adenine (L-2, xSolv = 2H(2)O, 2), 2-chloro-N6-furfuryladenine (L-3, 3), 2-chloro-N6-(5-methylfurfuryl)adenine (L-4, 4) and 2-chloro-N6-furfuryl-9-isopropyladenine (L-5, 5), as N-donor ligands has been synthesized. The complexes have been fully characterized by elemental analyses (C, H, N), FTIR, Raman, H-1 and C-13 NMR spectroscopy, conductivity measurements, thermogravimetric (TG) and differential thermal (DTA) analyses. Single crystal X-ray analysis determined the molecular structures of 2-chloro-N6-furfuryl-9-isopropyladenine (L-5) and the complex [Zn(L-1)(2)Cl-2]center dot CH3OH. The Zn(II) ion is tetrahedrally coordinated by two chlorido ligands and two molecules of the L-1 organic compound. The two ligands L-1 are coordinated to the central Zn(II) ion via the N7 atoms. This conclusion can also be drawn from multinuclear NMR spectroscopic experiments. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.02.004
• 作为产物：
  描述：

  2,6-二氯嘌呤 、 5-甲基糠胺 以 四氢呋喃 为溶剂， 反应 72.0h， 生成 2-chloro-N6-(5-methylfurfuryl)adenine
  参考文献：
  名称：

  [EN] DERIVATIVES OF ADENINE AND 8-AZA-ADENINE AND USES THEREOF-796
  [FR] DÉRIVÉS DE L'ADÉNINE ET DE LA 8-AZA-ADÉNINE ET LEURS UTILISATIONS

  摘要：

  该发明涉及化合物或其药用可接受的盐，其化学式为（I）：具有细菌MurI抑制活性，因此可用于治疗和预防细菌感染，例如E.faecalis或E. faecium感染。此外，该发明涉及人体或动物体的治疗方法。该发明还涉及化合物的制造方法，含有这些化合物的药物组合物，以及它们在制造用于治疗和预防人类等恒温动物各种细菌疾病的药物中的应用。

  公开号：

  WO2009034386A1

文献信息

• Structurally varied Cu(II) complexes involving kinetin and its derivatives: Synthesis, characterization and evaluation of SOD-mimic activity
  作者：Radka Novotná、Radovan Herchel、Zdeněk Trávníček

  DOI：10.1016/j.poly.2011.12.016

  日期：2012.2

  Three new structural types of Cu(II) complexes of kinetin and its purine- and/or furan-substituted derivatives (HLn), involving acetato-bridges (Ac) or mixed N-donor ligands, are reported. Complexes of the compositions [Cu-2(mu(3)-L-1)(2)(mu(2)-Ac)(2)](n) (1). [Cu-2(mu(3)-L-2)(2)(mu(2)-Ac)(2)](n) (2), [Cu-2(mu(3)-L-3)(2)(mu(2)-AC)(2)](n) (3), [Cu-2(mu(2)-AC)(4)(HL5)(2)] (4), [Cu-2(mu(2)-Ac)(4)(HL6)(2)] (5), [Cu(H2O)(2)(L-3)(2)(Phen)] (6) and [Cu(H2O)(2)(L-4)(2)(Phen)]center dot 2H(2)O (7), with kinetin (N6-furfuryladenine, HL1) and its derivatives N6-(5-methylfurfuryl)adenine (HL2), 2-chloro-N6-furfuryladenine (HL3), 2-chloro-N6-(5-methylfurfuryl)adenine (HL4), 2-chloro-N6-furfury19-isopropyladenine (HL5) and 2-chloro-N6-(5-methylfurfuryl)-9-isopropyladenine (HL6) (phen = 1, 10-phenanthroline), have been fully characterized by elemental analyses, FTIR, electronic spectroscopy, conductivity, temperature dependent magnetic susceptibility measurements, thermogravimetric (TG) and differential thermal (DTA) analyses. The geometry around the Cu(II) centers is square pyramidal in the two structural groups involving the acetato bridges (1-3, and 4,5) and octahedral in the mononuclear 6 and 7. This was confirmed by single crystal X-ray analysis for the dimeric complexes 4 and 5, with each Cu(II) atom five-coordinated by four 0 atoms from the acetato bridges and one N7 atom from the adenine moiety of HLn. The length of the Cu center dot center dot center dot Cu separation present in the dimers 4 and 5 is equal to 2.6508(6) and 2.6523(4) A, respectively. The anti-radical activity of the presented complexes was evaluated by an in vitro SOD-mimic assay and the best results were found for 4 with IC50 equal to 57.41,mu M. (C) 2011 Elsevier Ltd. All rights reserved.
• Zinc(II) chlorido complexes of protonated kinetin and its derivatives: Synthesis, properties and X-ray structure of [Zn(Hkinetin)Cl3]·kinetin
  作者：Radka Novotná、Igor Popa、Zdeněk Trávníček

  DOI：10.1016/j.ica.2010.08.040

  日期：2011.1

  The syntheses and characterization of five novel zinc(II) complexes with protonated kinetin (6-furfurylaminopurine) and its derivatives are described. Based on the results following from elemental analyses (C, H, N), FTIR, Raman, H-1 and C-13 NMR spectroscopy, conductivity measurements, thermogravimetric (TG) and differential thermal analyses (DTA), and single crystal X-ray analysis, the complexes of the general composition [Zn(HLn)Cl-3]center dot xL(n) (1-5) have been prepared, where L-1 = kinetin (6-furfurylaminopurine), L-2 = 6-(5-methylfurfurylamino) purine, L-3 = 2-chloro-6-furfurylaminopurine, L-4 = 2-chloro-6-(5-methylfurfurylamino) purine and L-5 = 2-chloro-6-furfurylamino-9-isopropylpurine, and x = 1/2-2. The structure of [Zn(HL1)Cl-3]center dot L-1 (1) has been determined by single crystal X-ray analysis. The Zn(II) atom is tetrahedrally coordinated by three chlorido ligands and one N3-protonated organic molecule forming a ZnCl3N donor set. The organic ligand L-1 is coordinated to the Zn(II) centre through the N7 atom of the purine moiety. NMR spectroscopic study confirmed the N3 and N7 atom to be the protonation, and coordination site, respectively. (C) 2010 Elsevier B.V. All rights reserved.
• [EN] DERIVATIVES OF ADENINE AND 8-AZA-ADENINE AND USES THEREOF-796<br/>[FR] DÉRIVÉS DE L'ADÉNINE ET DE LA 8-AZA-ADÉNINE ET LEURS UTILISATIONS
  申请人：ASTRAZENECA AB

  公开号：WO2009034386A1

  公开（公告）日：2009-03-19

  The invention relates to chemical compounds, or pharmaceutically acceptable salts thereof of the formula (I): which have bacterial MurI inhibitory activity and are accordingly useful for their treatment and prophylaxis of bacterial infection, e.g., E.faecalis or E. faeciuminfection. Further, the invention relates to methods of treatment of the human or animal body. The invention also relates to processes for the manufacture of the compounds, to pharmaceutical compositions containing them, and to their use in the manufacture of medicaments of use in the treatment and prevention of various bacterial diseases in a warm-blooded animalsuch as man.

  该发明涉及化合物或其药用可接受的盐，其化学式为（I）：具有细菌MurI抑制活性，因此可用于治疗和预防细菌感染，例如E.faecalis或E. faecium感染。此外，该发明涉及人体或动物体的治疗方法。该发明还涉及化合物的制造方法，含有这些化合物的药物组合物，以及它们在制造用于治疗和预防人类等恒温动物各种细菌疾病的药物中的应用。
• Synthesis and characterization of the first zinc(II) complexes involving kinetin and its derivatives: X-ray structures of 2-chloro-N6-furfuryl-9-isopropyladenine and [Zn(kinetin)2Cl2]·CH3OH
  作者：Radka Novotná、Zdeněk Trávníček、Igor Popa

  DOI：10.1016/j.ica.2010.02.004

  日期：2010.6

  A series of the first zinc(II) complexes of the general composition [Zn(L-n)(2)Cl-2]center dot xSolv (1-5) involving kinetin [N6-furfuryladenine, L-1, xSolv = CH3OH, complex 1] and its derivatives, i.e. N6-(5-methylfurfuryl)adenine (L-2, xSolv = 2H(2)O, 2), 2-chloro-N6-furfuryladenine (L-3, 3), 2-chloro-N6-(5-methylfurfuryl)adenine (L-4, 4) and 2-chloro-N6-furfuryl-9-isopropyladenine (L-5, 5), as N-donor ligands has been synthesized. The complexes have been fully characterized by elemental analyses (C, H, N), FTIR, Raman, H-1 and C-13 NMR spectroscopy, conductivity measurements, thermogravimetric (TG) and differential thermal (DTA) analyses. Single crystal X-ray analysis determined the molecular structures of 2-chloro-N6-furfuryl-9-isopropyladenine (L-5) and the complex [Zn(L-1)(2)Cl-2]center dot CH3OH. The Zn(II) ion is tetrahedrally coordinated by two chlorido ligands and two molecules of the L-1 organic compound. The two ligands L-1 are coordinated to the central Zn(II) ion via the N7 atoms. This conclusion can also be drawn from multinuclear NMR spectroscopic experiments. (C) 2010 Elsevier B.V. All rights reserved.