4,9-dimethoxynaphtho[2,3-b]furan | 189763-01-7

• 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: 4,9-dimethoxynaphtho[2,3-b]furan
• 英文别名: 4,9-dimethoxybenzo[f][1]benzofuran
• CAS: 189763-01-7
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: ZTVWLBMIFFSWBQ-UHFFFAOYSA-N

物化性质

• 沸点：
  372.7±22.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  31.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,9-dimethoxynaphtho[2,3-b]furan 在 正丁基锂 、 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 7.33h， 生成 2-乙酰基呋喃并-1,4-萘醌
  参考文献：
  名称：

  一种新的合成路线，以2-取代的萘并[2,3- b ]呋喃-4,9-二dione2-取代萘并[2,3- b ]呋喃-4,9-二酮

  摘要：

  4,9-二甲氧基萘并[2,3- b ]呋喃9是在91％的收率得到经由萘并[2,3-的还原甲基化b ]呋喃-4,9-二酮2。用丁基锂处理9后，使混合物与N，N-二甲基乙酰胺反应，然后用硝酸铈（IV）二铵氧化，得到2-乙酰基萘[2,3 - b ]呋喃-4,9-二酮1。2- Formylnaphtho [2,3- b ]呋喃-4,9-二酮13和2-三甲基甲硅烷-萘并[2,3- b ]呋喃-4,9-二酮14也从获得9通过类似的方法。的halodesilylations 14容易得到2- iodonaphtho [2,3- b ]呋喃-4,9-二酮16，2-bromonaphtho [2,3- b ]呋喃-4,9-二酮17，和2- chloronaphtho [2- ，3 - b ]呋喃-4,9-二酮18的产率分别为82％，93％和83％。此外，14的氮杂硅烷基化以77％的产率得到2-硝基萘[2,3

  DOI：

  10.1002/jhet.5570340209
• 作为产物：
  描述：

  4,9-dioxo-4,9-dihydronaphtho[2,3-b]furan-2-carbaldehyde 在 喹啉 、 sodium dithionite 、 copper chromite 、 四丁基溴化铵 、 双氧水 、 溶剂黄146 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 4,9-dimethoxynaphtho[2,3-b]furan
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationships of Lapacho Analogues. 1. Suppression of Human Keratinocyte Hyperproliferation by 2-Substituted Naphtho[2,3-b]furan-4,9-diones, Activation by Enzymatic One- and Two-Electron Reduction, and Intracellular Generation of Superoxide

  摘要：

  A series of linearly anellated lapacho quinone analogues substituted at the 2-position of the tricyclic naphtho-[2,3-b]furan-4,9-dione system were synthesized and evaluated for their ability to suppress keratinocyte hyperproliferation using HaCaT cells as the primary test system. While very good in vitro potency with IC50 values in the submicromolar range was attained with electron-withdrawing substituents, some compounds were found to induce plasma membrane damage, as evidenced by the release of LDH activity from cytoplasm of the keratinocytes. The most potent analogue against keratinocyte hyperproliferation was the 1,2,4-oxadiazole 18, the potency of which was combined with comparably low cytotoxic membrane damaging effects. Structure-activity relationship studies with either metabolically stable or labile analogues revealed that the quinone moiety was required for activity. Selected compounds were studied in detail for their capability to generate superoxide radicals both in isolated enzymatic one- and two-electron reduction assays as well as in a HaCaT cell-based assay.

  DOI：

  10.1021/jm3009597

文献信息

• NAPHTHOQUINONES FOR DISEASE THERAPIES
  申请人：Jiang Zhiwei

  公开号：US20130150437A1

  公开（公告）日：2013-06-13

  The present invention discloses novel naphtho[2,3-b]furan-4,9-diones and naphtho[2,3-b]thiophene-4,9-diones and methods of making and using the same. The present invention also discloses pharmaceutical compositions comprising novel naphtho[2,3-b]furan-4,9-dione or naphtho[2,3-b]thiophene-4,9-diones for the treatment of various indications including proliferative diseases.

  本发明公开了新型的萘并[2,3-b]呋喃-4,9-二酮和萘并[2,3-b]噻吩-4,9-二酮及其制造和使用方法。本发明还公开了包含新型萘并[2,3-b]呋喃-4,9-二酮或萘并[2,3-b]噻吩-4,9-二酮的药物组合物，用于治疗包括增殖性疾病在内的各种适应症。
• [EN] NOVEL ANPHTHOQUINONES FOR DISEASE THERAPIES<br/>[FR] NOUVELLES NAPHTOQUINONES À USAGE THÉRAPEUTIQUE
  申请人：ZHOUSHAN HAIZHONGZHOU XINSHENG PHARMACEUTICALS CO LTD

  公开号：WO2012024818A1

  公开（公告）日：2012-03-01

  Naphtho[2,3-b]furan-4,9-diones and naphtho[2,3-b]thiophene-4,9-diones, the preparation methods and uses thereof are disclosed. The pharmaceutical compositions comprising such compounds for the treatment of various indications including proliferative diseases are also disclosed.

  萘并[2,3-b]呋喃-4,9-二酮和萘并[2,3-b]噻吩-4,9-二酮的制备方法及其用途被公开。还公开了包含这些化合物的药物组合物，用于治疗包括增殖性疾病在内的各种疾病。
• [EN] NOVEL ESTERS OF 4,9-DIHYDROXY-NAPHTHO[2,3-b]FURANS FOR DISEASE THERAPIES<br/>[FR] NOUVEAUX ESTERS DE 4,9-DIHYDROXY-NAPHTO[2,3-B]FURANNES POUR TRAITEMENT THÉRAPEUTIQUE DE MALADIES
  申请人：ZHOUSHAN HAIZHONGZHOU XINSHENG PHARMACEUTICALS CO LTD

  公开号：WO2012119265A1

  公开（公告）日：2012-09-13

  The present invention discloses esters of 4,9-dihydroxy-naphtho[2,3-b]furans and methods of making and using the same. The present invention also discloses conversion of the esters into therapeutically active 4,9-dihydroxy-naphtho[2,3-b]furans in vivo. The present invention furthermore discloses pharmaceutical compositions comprising the esters of 4,9- dihydroxy-naphtho[2,3-b]furans for the treatment of various indications including proliferative diseases.

  本发明公开了4,9-二羟基萘并[2,3-b]呋喃的酯类及其制造和使用方法。本发明还公开了将这些酯转化为体内治疗活性4,9-二羟基萘并[2,3-b]呋喃的方法。本发明进一步公开了包含4,9-二羟基萘并[2,3-b]呋喃的酯类的药物组合物，用于治疗包括增殖性疾病在内的各种疾病。
• NOVEL ESTERS OF 4, 9-DIHYDROXY-NAPHTHO [2, 3-b] FURANS FOR DISEASE THERAPIES
  申请人：Jiang Zhiwei

  公开号：US20130345176A1

  公开（公告）日：2013-12-26

  The present invention discloses esters of 4,9-dihydroxy-naphtho[2,3-b]furans and methods of making and using the same. The present invention also discloses conversion of the esters into therapeutically active 4,9-dihydroxy-naphtho[2,3-b]furans in vivo. The present invention furthermore discloses pharmaceutical compositions comprising the esters of 4,9-dihydroxy-naphtho[2,3-b]furans for the treatment of various indications including proliferative diseases.

  本发明公开了4,9-二羟基萘并[2,3-b]呋喃的酯类及其制造和使用方法。本发明还公开了将这些酯转化为体内治疗活性4,9-二羟基萘并[2,3-b]呋喃的方法。本发明进一步公开了包含4,9-二羟基萘并[2,3-b]呋喃的酯类的药物组合物，用于治疗包括增殖性疾病在内的各种疾病。
• 一类Napabucasin的衍生物及其药物用途
  申请人：毕庶壮

  公开号：CN113214201B

  公开（公告）日：2023-08-15

  一类Napabucasin的衍生物及其药物用途，结构符合通式(I)所述的大部分化合物的水溶解性显著高于Napabucasin。该类化合物及其药学上可接受的盐可用于制备抗肿瘤的药物，且大部分化合物的细胞抑制活性明显优于Napabucasin。同时实验表明该类化合物具有极强的抗幽门螺杆菌和抗真菌活性，可用于制备抗幽门螺杆菌和真菌感染的药物。