5-amino-8-methoxypsoralen | 49739-65-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 5-amino-8-methoxypsoralen
• 英文别名: 4-Amino-9-methoxy-7H-furo(3,2-g)chromen-7-one；4-amino-9-methoxyfuro[3,2-g]chromen-7-one
• CAS: 49739-65-3
• 化学式: C₁₂H₉NO₄
• 分子量: 231.208
• InChiKey: MONZOXMQHOAEQD-UHFFFAOYSA-N

物化性质

• 熔点：
  234-235 °C
• 沸点：
  485.6±45.0 °C(Predicted)
• 密度：
  1.442±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-amino-8-methoxypsoralen 在 盐酸 、 sodium nitrite 作用下， 生成 4-羟基异虎耳草素; 4-羟基异茴芹内酯; 5-羟基-8-甲氧基补骨脂素
  参考文献：
  名称：

  Psoralene I: Certain Reactions of Xanthotoxin^*

  摘要：

  DOI：

  10.1021/jo01098a023
• 作为产物：
  描述：

  欧前胡素 在 盐酸 、 tin 、 硝酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 生成 5-amino-8-methoxypsoralen
  参考文献：
  名称：

  Synthesis and evaluation of linear furanocoumarins as potential anti-breast and anti-prostate cancer agents

  摘要：

  A series of 22 furanocoumarin derivatives were synthesized and evaluated for cytotoxicity against breast cancer (MCF-7 and MDA-MB-231) and prostate cancer (PC-3) cell lines along with normal cell line. Several analogs were synthesized by replacing prenyl moiety with alkyl, aromatic, and heteroaromatic functionality to study the structure-activity relationship. Compounds 20 and 22 with adamantoylamino, diprenylamino and substituted benzene sulfonamide substituents showed potent antiproliferative activity in MCF-7 cell line with IC50 values of 0.48 and 0.53 A mu M, respectively. Both the compounds showed higher IC50 value in MCF-10A cell lines indicating nontoxicity in normal cell lines.

  DOI：

  10.1007/s00044-014-1312-6

文献信息

• Synthesis and antitumor activity of some new xanthotoxin derivatives
  作者：Omaima M. Abdel Hafez、Kamellia M. Amin、Nehad A. Abdel-Latif、Tahia K. Mohamed、Eman Y. Ahmed、Timothy Maher

  DOI：10.1016/j.ejmech.2009.01.006

  日期：2009.7

  derivative 6 was cyclized by the reaction with monochloroacetic acid in the presence of sodium acetate to give aminothiazolidinone derivative 7, but when the same reaction is carried out in the presence of pyridine, the thioxoimidazolidinone 8 was formed. The condensation of xanthotoxin sulphonamide with aromatic aldehydes gave the aryliminosulphonyl derivatives 9a–e. Xanthotoxin sulphonyl hydrazine condensed

  4-氨基-9-甲氧基补骨脂素（4-氨基黄体毒素）与一些芳香族醛的缩合导致形成4-芳基嘌呤黄体毒素衍生物2a - h，将其与巯基乙酸环化，得到噻唑烷酮衍生物3a - h。另一方面，氨基黄嘌呤毒素1与某些酸酐的反应可制得4-亚氨基二酮衍生物3a - d。当1与一些异硫氰酸酯反应时，获得硫脲衍生物5a – c，但是当1与1时获得硫脲衍生物6与硫氰酸铵反应。通过在乙酸钠存在下与一氯乙酸反应使硫脲衍生物6环化，得到氨基噻唑烷酮衍生物7，但是当在吡啶存在下进行相同反应时，形成了硫代氧杂咪唑烷酮8。花椒毒素磺酰胺与芳族醛的缩合得到芳基亚磺酰基衍生物9a - e。将花椒毒素磺酰肼与一些酸酐缩合，得到磺酸酰亚胺衍生物10a – c。9的抗肿瘤和细胞毒性活性 测试了合成的衍生物，发现有5种化合物具有活性，它们抑制了HeLa细胞的生长。
• 8-甲氧基补骨脂素的结构修饰物及其制备方 法与应用
  申请人：北京农学院

  公开号：CN109503612B

  公开（公告）日：2020-06-16

  本发明公开了8‑甲氧基补骨脂素的结构修饰物及其制备方法与应用。本发明所提供的8‑甲氧基补骨脂素的结构修饰物为式1所示的化合物B20或式2所示的化合物A10。化合物B20在64μg/mL的浓度下对产肠毒素大肠杆菌的抑菌活性是8‑甲氧基补骨脂素的2.3倍；化合物A10在64μg/mL的浓度下对产肠毒素大肠杆菌的抑菌活性是8‑甲氧基补骨脂素的2.4倍。本发明的化合物B20和化合物A10可用于制备治疗和/或预防仔猪腹泻的药物。
• EXPLORATORY PHOTOCHEMISTRY OF 5-AZIDO-8-ALKOXY-SUBSTITUTED PSORALENS FREE AND BOUND TO DNA
  作者：Tongqian Chen、Jacek Michalak、Matthew S. Platz

  DOI：10.1111/j.1751-1097.1995.tb09875.x

  日期：1995.6

  5‐Azido‐8‐alkoxy psoralens were synthesized. Laser flash photolysis (LFP: XeF, 351 nm, 55 mJ, 17 ns) of the azides in acetonitrile or benzene solution produces the triplet nitrene and a small amount of ketenimine. Laser flash photolysis of the azides in methanol or aqueous solution cleanly produces the triplet nitrene. In aqueous solution containing highly polymerized calf thymus DNA, LFP produces

  合成了 5-叠氮基-8-烷氧基补骨脂素。叠氮化物在乙腈或苯溶液中的激光闪光光解 (LFP: XeF, 351 nm, 55 mJ, 17 ns) 产生三线态氮烯和少量烯酮亚胺。叠氮化物在甲醇或水溶液中的激光闪光光解干净地产生三线态氮烯。在含有高度聚合的小牛胸腺 DNA 的水溶液中，LFP 产生三线态氮烯和烯酮亚胺的混合物，分别对应于游离和结合补骨脂素的光解。这两种瞬变缓慢衰减，但衰减速率不同。瞬态光谱的分配由矩阵 EPR 和紫外可见光谱确定。三线态氮烯寿命在缓冲液中以及存在和不存在小牛胸腺 DNA 的情况下是相同的。
• Nitrations of 4′,5′-dihydropsoralens: A route to radiopharmaceutical precursors
  作者：Ned D. Heindel、Natalie Foster、Thankamma Varkey

  DOI：10.1002/jhet.5570230564

  日期：1986.9

  furocoumarin, methoxsalen, which yields a single nitration product, the nitration of the 4′,5′-dihydro compound generates a condition-variant mixture of three nitro products. Reduction, diazotization, and pyrrolidine-trapping of one of these, the 4′,5′-dihydro-5-nitro-8- methoxypsoralen, provides a pyrrolidine triazene precursor for radioiodination of the dihydropsoralen system.

  与产生单一硝化产物的全芳族呋喃香豆素甲氧沙林的硝化不同，4'，5'-二氢化合物的硝化生成三种硝基产物的条件变量混合物。其中之一（4'，5'-二氢-5-硝基-8-甲氧基补骨脂素）的还原，重氮化和吡咯烷捕集为二氢补骨脂素系统的放射性碘化提供了吡咯烷三氮烯前体。
• Structural modification of a specific antimicrobial lead against Helicobacter pylori discovered from traditional Chinese medicine and a structure–activity relationship study
  作者：Bang-Le Zhang、Cheng-Qi Fan、Lei Dong、Fang-Dao Wang、Jian-Min Yue

  DOI：10.1016/j.ejmech.2010.08.045

  日期：2010.11

  Psoralen (1a) was found to be a specific and potent antimicrobial lead against Helicobacter pylori (H. pylori) from a traditional Chinese medicine (TCM) in the bioassay directed isolation. A series of structurally diverse analogues of la were thus designed and synthesized to improve the antimicrobial potency, some of which showed more potent activities than the lead compound (1a) against H. pylori. Among them, compound 25a is 16-fold stronger (MIC = 0.39 mu g/mL) than 1a (MIC = 6.25 mu g/mL), and is even potent than the positive control metronidazole (MIC = 0.50 mu g/mL). The in vitro antimicrobial activities against H. pylori of these structurally diverse analogues based on the scaffold of la have also led to an outline of structure-activity relationship. (C) 2010 Elsevier Masson SAS. All rights reserved.