Naphtho [1,2-b]furan-5,6-dicarboxylic anhydride | 167541-83-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: Naphtho [1,2-b]furan-5,6-dicarboxylic anhydride
• 英文别名: Naphtho[1,2-b]furan-5,6-dicarboxylic Anhydride；3,11-dioxatetracyclo[7.6.1.05,16.010,14]hexadeca-1(16),5,7,9,12,14-hexaene-2,4-dione
• CAS: 167541-83-5
• 化学式: C₁₄H₆O₄
• 分子量: 238.199
• InChiKey: MQMCVCIBFPJNGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-[bis(2-aminoethyl)]-N,N'-dimethyl-1,3-propanediamine 、 Naphtho [1,2-b]furan-5,6-dicarboxylic anhydride 以 乙醇 、 甲苯 为溶剂， 以27%的产率得到3-[2-[3-[2-(2,4-Dioxo-11-oxa-3-azatetracyclo[7.6.1.05,16.010,14]hexadeca-1(16),5,7,9,12,14-hexaen-3-yl)ethyl-methylamino]propyl-methylamino]ethyl]-11-oxa-3-azatetracyclo[7.6.1.05,16.010,14]hexadeca-1(16),5,7,9,12,14-hexaene-2,4-dione
  参考文献：
  名称：

  New Analogues of Amonafide and Elinafide, Containing Aromatic Heterocycles:  Synthesis, Antitumor Activity, Molecular Modeling, and DNA Binding Properties

  摘要：

  Amonafide- and elinafide-related mono and bisintercalators, modified by the introduction of a, pi -excedent furan or thiophene ring fused to the naphthalimide moiety, have been synthesized. These compounds have shown an interesting antitumor profile. The best compound, 9, was 2.5-fold more potent than elinafide against human colon carcinoma cells (HT-29). Molecular dynamic simulations and physicochemical experiments have demonstrated that these compounds are capable of forming stable DNA complexes. These results, together with those previously reported by us for imidazo- and pyrazinonaphthalimide analogues, have prompted us to propose that the DNA binding process does not depend on the electronic nature of the fused heterocycle.

  DOI：

  10.1021/jm0308850
• 作为产物：
  描述：

  2-(2-甲氧基-2-氧代乙基)苯羧酸甲酯 在 碘 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.25h， 生成 Naphtho [1,2-b]furan-5,6-dicarboxylic anhydride
  参考文献：
  名称：

  New Analogues of Amonafide and Elinafide, Containing Aromatic Heterocycles:  Synthesis, Antitumor Activity, Molecular Modeling, and DNA Binding Properties

  摘要：

  Amonafide- and elinafide-related mono and bisintercalators, modified by the introduction of a, pi -excedent furan or thiophene ring fused to the naphthalimide moiety, have been synthesized. These compounds have shown an interesting antitumor profile. The best compound, 9, was 2.5-fold more potent than elinafide against human colon carcinoma cells (HT-29). Molecular dynamic simulations and physicochemical experiments have demonstrated that these compounds are capable of forming stable DNA complexes. These results, together with those previously reported by us for imidazo- and pyrazinonaphthalimide analogues, have prompted us to propose that the DNA binding process does not depend on the electronic nature of the fused heterocycle.

  DOI：

  10.1021/jm0308850

文献信息

• Polycyclic and heterocyclic chromophores for bis-imide tumoricidals
  申请人：The Du Pont Merck Pharmaceutical Company

  公开号：US05416089A1

  公开（公告）日：1995-05-16

  Anticancer compounds of formula I: ##STR1## and pharmaceutically acceptable salts thereof, wherein: R.sup.1, R.sup.2 and R.sup.3 are independently selected H, CH.sub.3, NH.sub.2, NO.sub.2, and CN; R.sup.9 and R.sup.10 are H or alkyl or halo, X.sup.1 and Y.sup.1 or X.sup.2 and Y.sup.2, when present, join together to form, independently, a six membered 1N heterocycle substituted with 1-2 R.sup.3 ; or the group: ##STR2## wherein one of W or Z is C.dbd.O and the other is C.dbd.O, NH, S or O; or when X.sup.2 and Y.sup.2 are not joined together and when R.sup.2 is in the 4-position, then X.sup.2 and R.sup.2 may join together to form an ethylene bridge; are disclosed.

  公式I的抗癌化合物：##STR1##及其药学上可接受的盐，其中：R.sup.1、R.sup.2和R.sup.3独立选择H、CH.sub.3、NH.sub.2、NO.sub.2和CN；R.sup.9和R.sup.10为H或烷基或卤素，当存在X.sup.1和Y.sup.1或X.sup.2和Y.sup.2时，它们独立地结合在一起形成一个六元1N杂环，被1-2个R.sup.3取代；或者该基团：##STR2## 其中W或Z之一为C.dbd.O，另一个为C.dbd.O、NH、S或O；或者当X.sup.2和Y.sup.2没有结合在一起且R.sup.2在4位时，那么X.sup.2和R.sup.2可以结合在一起形成一个乙烯桥。
• US5416089A
  申请人：——

  公开号：US5416089A

  公开（公告）日：1995-05-16
• US5585382A
  申请人：——

  公开号：US5585382A

  公开（公告）日：1996-12-17
• [EN] BIS-IMIDE POLYCYCLIC AND HETEROCYCLIC CHROMOPHORES USEFUL AS TUMORICIDALS<br/>[FR] CHROMOPHORES BIS-IMIDE POLYCYCLIQUES ET HETEROCYCLIQUES UTILES COMME AGENTS ANTICANCEREUX
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：WO1995000490A1

  公开（公告）日：1995-01-05

  (EN) This invention relates to bis-imide derivatives of tri- and tetraamines of formula (I), pharmaceutical compositions containing them, and methods of using them to treat cancer, particularly solid tumors, in mammals.(FR) Cette invention concerne des dérivés bis-imide de triamines et de tétraamines de la formule (I), des compositions pharmaceutiques les contenant et des méthodes d'utilisation de celles-ci pour traiter le cancer, en particulier les tumeurs solides chez les mammifères.
• New Analogues of Amonafide and Elinafide, Containing Aromatic Heterocycles:  Synthesis, Antitumor Activity, Molecular Modeling, and DNA Binding Properties
  作者：Miguel F. Braña、Mónica Cacho、Mario A. García、Beatriz de Pascual-Teresa、Ana Ramos、M. Teresa Domínguez、José M. Pozuelo、Cristina Abradelo、María Fernanda Rey-Stolle、Mercedes Yuste、Mónica Báñez-Coronel、Juan Carlos Lacal

  DOI：10.1021/jm0308850

  日期：2004.3.1

  Amonafide- and elinafide-related mono and bisintercalators, modified by the introduction of a, pi -excedent furan or thiophene ring fused to the naphthalimide moiety, have been synthesized. These compounds have shown an interesting antitumor profile. The best compound, 9, was 2.5-fold more potent than elinafide against human colon carcinoma cells (HT-29). Molecular dynamic simulations and physicochemical experiments have demonstrated that these compounds are capable of forming stable DNA complexes. These results, together with those previously reported by us for imidazo- and pyrazinonaphthalimide analogues, have prompted us to propose that the DNA binding process does not depend on the electronic nature of the fused heterocycle.