6-chloroprotocatechualdehyde | 37686-56-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 6-chloroprotocatechualdehyde
• 英文别名: 6-chloro-3,4-dihydroxybenzaldehyde；6-Chlor-3,4-dioxybenzaldehyd；6-Chlorprotocatechualdehyd；6-Chlor-protocatechuealdehyd；2-chloro-4,5-dihydroxy-benzaldehyde；2-Chlor-4,5-dihydroxy-benzaldehyd；2-Chlor-protocatechualdehyd；2-Chloro-4,5-dihydroxybenzaldehyde
• CAS: 37686-56-9
• 化学式: C₇H₅ClO₃
• 分子量: 172.568
• InChiKey: VVCAFCGTTRGXOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloroprotocatechualdehyde 在 zinc(II) iodide 作用下， 生成 (4,5-Bis-benzyloxy-2-chloro-phenyl)-trimethylsilanyloxy-acetonitrile
  参考文献：
  名称：

  Squier; Van der Schyf; Oliver, Arzneimittel-Forschung/Drug Research, 1986, vol. 36, # 3, p. 457 - 460

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯-4-羟基-5-甲氧基苯甲醛 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以88%的产率得到6-chloroprotocatechualdehyde
  参考文献：
  名称：

  Chemical degradation products of lignin and humic substances Part II Synthesis, structure verification and liquid chromatographic separation of chlorinated protocatechualdehydes (3,4-dihydroxy-benzaldehydes), 5-hydroxyvanillins (3,4-dihydroxy-5-methoxy-benzaldehydes) and gallaldehydes (3,4,5-trihydroxybenzaldehydes)

  摘要：

  All possible chloroprotocatechualdehydes, chlorogalladehydes, 5-bromoprotoratechualdehyde and chloro-5-hydroxyvanillins except 2-chloro-5-hydroxyvanillin) were synthesized. Their purity and structures were examined by liquid chromatography, mass spectrometry and other spectroscopic measurements. The details of the synthesis, liquid chromatographic separation and mass spectrometric features are discussed.

  DOI：

  10.1016/0045-6535(94)90423-5

文献信息

• Halogen substituted .alpha.-(aminoalkyl)-3,4-dihydroxybenzyl alcohols
  申请人：SmithKline Corporation

  公开号：US03976695A1

  公开（公告）日：1976-08-24

  Halogen substituted .alpha.-(aminoalkyl)-3,4-dihydroxybenzyl alcohols having .beta.-adrenergic stimulant activity, particularly as selective bronchodilators. The .alpha.-aminomethyl derivatives are prepared by the condensation of an appropriately substituted styrene oxide with a primary amine followed by removal of the ether protective group(s). The .alpha.-aminoethyl or .alpha.-aminopropyl derivatives are prepared by the condensation of an appropriately substituted .alpha.-bromoalkyl phenyl ketone with an N-benzyl secondary amine followed by reduction of the ketone moiety and removal of the ether protective group(s).

  卤代.alpha.-(氨基烷基)-3,4-二羟基苯甲醇具有.beta.-肾上腺素能兴奋作用，特别是作为选择性支气管扩张剂。.alpha.-氨甲基衍生物通过适当取代的苯乙烯氧化物与一级胺的缩合反应制备，然后去除醚保护基。.alpha.-氨乙基或.alpha.-氨丙基衍生物通过适当取代的.alpha.-溴代烷基苯酮与N-苄基二级胺的缩合反应制备，然后还原酮基团并去除醚保护基(s)。
• PYRAZOLO-HETEROARYL COMPOUNDS
  申请人：Revesz Lászlo

  公开号：US20090258874A1

  公开（公告）日：2009-10-15

  A compound of formula I wherein the groups R1-R4, X and Y are as defined in the specification, useful to treat TNF-Alpha and IL-1 mediated diseases.

  化合物I的公式为其中R1-R4，X和Y的基团如规范中所定义，可用于治疗TNF-Alpha和IL-1介导的疾病。
• WO2006/63820
  申请人：——

  公开号：——

  公开（公告）日：——
• Uracil-Directed Ligand Tethering:  An Efficient Strategy for Uracil DNA Glycosylase (UNG) Inhibitor Development
  作者：Yu Lin Jiang、Daniel J. Krosky、Lauren Seiple、James T. Stivers

  DOI：10.1021/ja055846n

  日期：2005.12.1

  Uracil DNA glycosylase (UNG) is an important DNA repair enzyme that recognizes and excises uracil bases in DNA using an extrahelical recognition mechanism. It is emerging as a desirable target for small-molecule inhibitors given its key role in a wide range of biological processes including the generation of antibody diversity, DNA replication in a number of viruses, and the formation of DNA strand breaks during anticancer drug therapy. To accelerate the discovery of inhibitors of UNG we have developed a uracil-directed ligand tethering strategy. In this efficient approach, a uracil aldehyde ligand is tethered via alkyloxyamine linker chemistry to a diverse array of aldehyde binding elements. Thus, the mechanism of extrahelical recognition of the uracil ligand is exploited to target the UNG active site, and alkyloxyamine linker tethering is used to randomly explore peripheral binding pockets. Since no compound purification is required, this approach rapidly identified the first small-molecule inhibitors of human UNG with micromolar to submicromolar binding affinities. In a surprising result, these uracil-based ligands are found not only to bind to the active site but also to bind to a second uncompetitive site. The weaker uncompetitive site suggests the existence of a transient binding site for uracil during the multistep extrahelical recognition mechanism. This very general inhibitor design strategy can be easily adapted to target other enzymes that recognize nucleobases, including other DNA repair enzymes that recognize other types of extrahelical DNA bases.
• Tomita et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1956, vol. 76, p. 1122,1125
  作者：Tomita et al.

  DOI：——

  日期：——