4,6,8,9-四甲基-1H-呋喃并[2,3-h]喹啉-2-酮 | 174022-40-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 4,6,8,9-四甲基-1H-呋喃并[2,3-h]喹啉-2-酮
• 中文别名: 1-环庚烯-1-胺
• 英文名称: 4,6,8,9-tetramethyl-2H-furo[2,3-h]quinolin-2-one
• 英文别名: 4,6,8,9-Tetramethyl-2H-furo(2,3-h)quinolin-2-one；4,6,8,9-tetramethyl-1H-furo[2,3-h]quinolin-2-one
• CAS: 174022-40-3
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: ZFHPBRXQLCICCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,6,8,9-四甲基-1H-呋喃并[2,3-h]喹啉-2-酮 在 硫酸 作用下， 反应 3.0h， 以10%的产率得到8-hydroxymethyl-4,6,9-trimethylfuro[2,3-h]quinolin-2(1H)-one
  参考文献：
  名称：

  DNA damage and biological effects induced by photosensitization with new N1-unsubstituted furo[2,3-h]quinolin-2(1H)-ones

  摘要：

  New furoquinolinones unsubstituted at the N-1 position were prepared and their photobiological activities we re studied in comparison with 4.6.8.9-tetramethylfuro[2,3-h]quinotin-2(1H)-one (HFQ) and 8-MOP. The anti-proliferative activity of furoquinolinones 3a-f was tested upon UVA irradiation in mammalian cells, studying DNA synthesis and clonal growth capacity. and in micro-organisms, evaluating T2 infectivity. Almost all compounds appeared to be more active than 8-MOP, and free of any mutagenic activity and skin phototoxicity. Among them, compound 3b was the most effective one. Similarly to HFQ, compound 3b appeared to be very active also in DNA damaging, forming monoadducts and DPCL - 0. but no ISC and DPCL > 0, both responsible for furocoumarin genotoxicity and phototoxicity. Moreover, Ehrlich ascites cells, photoinactivated by the new furoquinolinone 3b and injected into recipient mice. proved to be capable of inducing protection against a successive challenge performed with the same tumor cells. For all these features. 3b seemed to be a new promising potential drug for PUVA therapy and photopheresis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00145-1
• 作为产物：
  描述：

  4,6-dimethyl-7-hydroxyquinolin-2-one 在 硫酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 40.5h， 生成 4,6,8,9-四甲基-1H-呋喃并[2,3-h]喹啉-2-酮
  参考文献：
  名称：

  角呋喃喹啉酮，补骨脂素类似物：皮肤疾病的新型抗增殖剂。合成，生物活性，作用机理和计算机辅助研究。

  摘要：

  为了获得新的潜在的光化学治疗剂，具有增加的抗增殖活性和减少的不良作用，我们制备了一些新的呋喃喹啉酮。已对其中两个进行了详细的研究：1,4,6,8-四甲基-2H-呋喃[2,3-h]-喹啉-2-酮（8）和4,6,8,9-四甲基- 2H-呋喃[2,3-h]喹啉-2-一（10）。这些化合物与DNA形成分子复合物，在双链大分子内部进行插入，如线性流二色性所示。通过随后用UV-A光照射，络合的配体与大分子光结合，仅形成具有胸腺嘧啶的顺式-syn构型的单环加合物。为了评估由位置1的8中的氮原子引起的电子效应，已对4,6,4'-三甲基Angelicin（TMA）和8进行了半经验计算。所得结果并未明确区分两个分子，在此近似水平下，这两个分子显示了与8、3,4-和4'的3,4-和8,9-烯烃键同时发生光反应的可能性， TMA的5'键。在插层8的较低能构象中，呋喃环转向多核苷酸的小沟，从而有利于该环与胸腺嘧啶的

  DOI：

  10.1021/jm950585l

文献信息

• METHOD FOR THE PREPARATION OF REAGENTS FOR AMPLIFICATION AND/OR DETECTION OF NUCLEIC ACIDS THAT EXHIBIT NO SIGNIFICANT CONTAMINATION BY NUCLEIC ACIDS
  申请人：Infectio Diagnostic (I.D.I.) INC.

  公开号：EP1497456A1

  公开（公告）日：2005-01-19
• Method for the preparation of reagents for amplification and/or detection of nucleic acids that exhibit no significant contamination by nucleic acids
  申请人：Picard J. Francois

  公开号：US20050037349A1

  公开（公告）日：2005-02-17

  The present invention decribes reagents free of detectable contaminating nucleic acids for performing highly sensitive and specific nucleic acids amplification and/or detection. It relates to an improvement in the technology of nucleic acid inactivation prior to nucleic acid testing (NAT) in order to prevent false-positive results. Specifically, this invention describes optimized and standardized reagents and ultra-violet treatment to achieve an effective and highly reproducible nucleic acid inactivation prior to NAT without substantially affecting the performance of the assay. More specifically, this nucleic acid inactivation process resulted in a reduction of up to four logs of the background signal associated with the PCR (polymerase chain reaction) amplification of DNA contaminating PCR reagents. This optimized and standardized method is also adaptable for use with NAT technologies other than PCR.
• [EN] METHOD FOR THE PREPARATION OF REAGENTS FOR AMPLIFICATION AND/OR DETECTION OF NUCLEIC ACIDS THAT EXHIBIT NO SIGNIFICANT CONTAMINATION BY NUCLEIC ACIDS<br/>[FR] PROCEDE DE PREPARATION DE REACTIFS POUR L'AMPLIFICATION ET/OU LA DETECTION D'ACIDE NUCLEIQUES NE PRESENTANT AUCUNE CONTAMINATION IMPORTANTE PAR DES ACIDES NUCLEIQUES
  申请人：INFECTIO DIAGNOSTIC INC

  公开号：WO2003087402A1

  公开（公告）日：2003-10-23

  The present invention decribes reagents free of detectable contaminating nucleic acids for performing highly sensitive and specific nucleic acids amplification and/or detection. It relates to an improvement in the technology of nucleic acid inactivation prior to nucleic acid testing (NAT) in order to prevent false-positive results. Specifically, this invention describes optimized and standardized reagents and ultra-violet treatment to achieve an effective and highly reproducible nucleic acid inactivation prior to NAT without substantially affecting the performance of the assay. More specifically, this nucleic acid inactivation process resulted in a reduction of up to four logs of the background signal associated with the PCR (polymerase chain reaction) amplification of DNA contaminating PCR reagents. This optimized and standardized method is also adaptable for use with NAT technologies other than PCR.
• DNA damage and biological effects induced by photosensitization with new N1-unsubstituted furo[2,3-h]quinolin-2(1H)-ones
  作者：Cristina Marzano、Adriana Chilin、Franco Bordin、Francarosa Baccichetti、Adriano Guiotto

  DOI：10.1016/s0968-0896(02)00145-1

  日期：2002.9

  New furoquinolinones unsubstituted at the N-1 position were prepared and their photobiological activities we re studied in comparison with 4.6.8.9-tetramethylfuro[2,3-h]quinotin-2(1H)-one (HFQ) and 8-MOP. The anti-proliferative activity of furoquinolinones 3a-f was tested upon UVA irradiation in mammalian cells, studying DNA synthesis and clonal growth capacity. and in micro-organisms, evaluating T2 infectivity. Almost all compounds appeared to be more active than 8-MOP, and free of any mutagenic activity and skin phototoxicity. Among them, compound 3b was the most effective one. Similarly to HFQ, compound 3b appeared to be very active also in DNA damaging, forming monoadducts and DPCL - 0. but no ISC and DPCL > 0, both responsible for furocoumarin genotoxicity and phototoxicity. Moreover, Ehrlich ascites cells, photoinactivated by the new furoquinolinone 3b and injected into recipient mice. proved to be capable of inducing protection against a successive challenge performed with the same tumor cells. For all these features. 3b seemed to be a new promising potential drug for PUVA therapy and photopheresis. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Angular Furoquinolinones, Psoralen Analogs:  Novel Antiproliferative Agents for Skin Diseases. Synthesis, Biological Activity, Mechanism of Action, and Computer-Aided Studies
  作者：Paolo Rodighiero、Adriano Guiotto、Adriana Chilin、Franco Bordin、Francarosa Baccichetti、Francesco Carlassare、Daniela Vedaldi、Sergio Caffieri、A. Pozzan、Francesco Dall'Acqua

  DOI：10.1021/jm950585l

  日期：1996.3.15

  With the aim of obtaining new potential photochemotherapeutic agents, having increased antiproliferative activity and decreased undesired effects, we have prepared some new furoquinolinones. Two of them have been studied in detail: 1,4,6,8-tetramethyl-2H-furo[2,3-h]-quinolin-2-one (8), and 4,6,8,9-tetramethyl-2H-furo[2,3-h]quinolin-2-one (10). These compounds form a molecular complex with DNA, undergoing

  为了获得新的潜在的光化学治疗剂，具有增加的抗增殖活性和减少的不良作用，我们制备了一些新的呋喃喹啉酮。已对其中两个进行了详细的研究：1,4,6,8-四甲基-2H-呋喃[2,3-h]-喹啉-2-酮（8）和4,6,8,9-四甲基- 2H-呋喃[2,3-h]喹啉-2-一（10）。这些化合物与DNA形成分子复合物，在双链大分子内部进行插入，如线性流二色性所示。通过随后用UV-A光照射，络合的配体与大分子光结合，仅形成具有胸腺嘧啶的顺式-syn构型的单环加合物。为了评估由位置1的8中的氮原子引起的电子效应，已对4,6,4'-三甲基Angelicin（TMA）和8进行了半经验计算。所得结果并未明确区分两个分子，在此近似水平下，这两个分子显示了与8、3,4-和4'的3,4-和8,9-烯烃键同时发生光反应的可能性， TMA的5'键。在插层8的较低能构象中，呋喃环转向多核苷酸的小沟，从而有利于该环与胸腺嘧啶的