2-(2-methyl-1,3-dioxolan-2-yl)naphtho[2,3-b]furan-4,9-dione

• 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: 2-(2-methyl-1,3-dioxolan-2-yl)naphtho[2,3-b]furan-4,9-dione
• 英文别名: 2-(2-methyl-1,3-dioxoran-2-yl)naphtho[2,3-b]furan-4,9-dione；2-(2-methyl-1,3-dioxolane-2-yl)naphtho[2,3-b]furan-4,9-dione；2-(2-Methyl-1,3-dioxolan-2-yl)benzo[f][1]benzofuran-4,9-dione
• 化学式: C₁₆H₁₂O₅
• 分子量: 284.268
• InChiKey: ZHMMFHPAOYPBER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-methyl-1,3-dioxolan-2-yl)naphtho[2,3-b]furan-4,9-dione 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 7.0h， 以94%的产率得到2-乙酰基呋喃并-1,4-萘醌
  参考文献：
  名称：

  METHOD FOR PRODUCING 2-ALKYLCARBONYLNAPHTHO[2,3-b]FURAN-4,9-DIONE-RELATED SUBSTANCE, AND SAID RELATED SUBSTANCE

  摘要：

  提供了一种用于生产与2-烷基碳酰萘[2,3-b]呋喃-4,9-二酮相关的物质的方法，该方法适合于工业规模生产。本发明提供：一种用于生产2-烷基碳酰[2,3-b]呋喃-4,9-二酮的中间体的生产方法，该方法包括在溶剂中，在金属或金属化合物和碱的存在下，将含有酮或醇的1-丁炔衍生物与在3位具有离去基团的2-羟基-1,4-萘醌衍生物反应；以及与中间体相关的物质。

  公开号：

  US20190062294A1
• 作为产物：
  描述：

  2-[5-(2-Methyl-[1,3]dioxolan-2-yl)-furan-3-carbonyl]-benzoic acid ethyl ester 在 sodium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 为溶剂， 反应 5.0h， 生成 2-(2-methyl-1,3-dioxolan-2-yl)naphtho[2,3-b]furan-4,9-dione
  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

文献信息

• Substituted naphtho[2,3-b]furans as water-soluble prodrugs for preventing and/or treating cancer
  申请人：BOSTON BIOMEDICAL, INC.

  公开号：US10183925B2

  公开（公告）日：2019-01-22

  The present invention provides compounds represented by formula (1A), or pharmaceutically acceptable salts. Compounds represented by formula (1A), or pharmaceutically acceptable salts thereof, wherein A1 and A2 are identical or different, and each independently —C(═O) B, —C(═O)CR3AR3BB, —CO2B, —C(═S)OB, —CONR3CB, —C(═S)NR3CB, a hydrogen atom, or the like, wherein A1 and A2 are not both hydrogen atoms, wherein B is an optionally substituted 3- to 12-membered monocyclic or polycyclic heterocyclic group, an optionally substituted 3- to 12-membered cyclic amino group, or a group represented by the following formula (B), wherein the 3- to 12-membered monocyclic or polycyclic heterocyclic group and the 3- to 12-membered cyclic amino group have at least one or more secondary nitrogen atoms in the ring; R1 is a hydrogen atom or the like; R2A, R2B, R2C, and R2D are identical or different, and each independently a hydrogen atom or the like; and R8 is alkyl. wherein * denotes a bonding position.

  本发明提供了式(1A)代表的化合物或其药学上可接受的盐。由式(1A)代表的化合物或其药学上可接受的盐，其中A1和A2相同或不同，且各自独立地为-C(═O)B、-C(═O)CR3AR3BB、-CO2B、-C(═S)OB、-CONR3CB、-C(═S)NR3CB、氢原子或类似物，其中A1和A2并非都是氢原子、其中 B 是任选取代的 3 至 12 元单环或多环杂环基团，任选取代的 3 至 12 元环状氨基基团，或下式（B）所代表的基团，其中 3 至 12 元单环或多环杂环基团和 3 至 12 元环状氨基基团在环中至少有一个或多个仲氮原子；R1为氢原子或类似物；R2A、R2B、R2C 和 R2D 相同或不同，且各自独立地为氢原子或类似物；以及 R8 为烷基。 其中 * 表示键合位置。
• Method for producing 2-alkylcarbonylnaphtho[2,3-b]furan-4,9-dione-related substance, and said related substance
  申请人：Sumitomo Dainippon Pharma Co., Ltd.

  公开号：US10738023B2

  公开（公告）日：2020-08-11

  Provided is a method for producing a 2-alkylcarbonylnaphtho[2,3-b]furan-4,9-dione-related substance, which is suitable for the production on an industrial scale. The present invention provides: a method for producing an intermediate for the production of a 2-alkylcarbonyl[2,3-b]furan-4,9-dione, which comprises reacting a 1-butyne derivative in which a ketone or an alcohol is protected with a 2-hydroxy-1,4-naphthoquinone derivative having a leaving group at position-3 in a solvent in the presence of a metal or a metal compound and a base; and a substance relating to the intermediate.

  本发明提供了一种生产 2-烷基羰基萘并[2,3-b]呋喃-4,9-二酮相关物质的方法，该方法适于工业化生产。本发明提供了：一种生产 2-烷基羰基[2,3-b]呋喃-4,9-二酮的中间体的方法，该方法包括在金属或金属化合物和碱存在下，在溶剂中使酮或醇被保护的 1-丁炔衍生物与位置-3 上有离去基团的 2-羟基-1,4-萘醌衍生物反应；以及一种与该中间体有关的物质。
• TW2016/39824
  申请人：——

  公开号：——

  公开（公告）日：——
• WATER-SOLUBLE PRODRUGS
  申请人：BOSTON BIOMEDICAL, INC.

  公开号：US20180111914A1

  公开（公告）日：2018-04-26

  The present invention provides compounds represented by formula (1A), or pharmaceutically acceptable salts. Compounds represented by formula (1A), or pharmaceutically acceptable salts thereof, wherein A 1 and A 2 are identical or different, and each independently —C(═O) B, —C(═O)CR 3A R 3B B, —CO 2 B, —C(═S)OB, —CONR 3C B, —C(═S)NR 3C B, a hydrogen atom, or the like, wherein A 1 and A 2 are not both hydrogen atoms, wherein B is an optionally substituted 3- to 12-membered monocyclic or polycyclic heterocyclic group, an optionally substituted 3- to 12-membered cyclic amino group, or a group represented by the following formula (B), wherein the 3- to 12-membered monocyclic or polycyclic heterocyclic group and the 3- to 12-membered cyclic amino group have at least one or more secondary nitrogen atoms in the ring; R 1 is a hydrogen atom or the like; R 2A , R 2B , R 2C , and R 2D are identical or different, and each independently a hydrogen atom or the like; and R 8 is alkyl. wherein * denotes a bonding position.
• SUBSTITUTED NAPHTHO[2,3-b]FURANS AS WATER-SOLUBLE PRODRUGS FOR PREVENTING AND/OR TREATING CANCER
  申请人：BOSTON BIOMEDICAL, INC.

  公开号：US20190084955A1

  公开（公告）日：2019-03-21

  The present invention provides compounds represented by formula (1A), or pharmaceutically acceptable salts. Compounds represented by formula (1A), or pharmaceutically acceptable salts thereof, wherein A 1 and A 2 are identical or different, and each independently —C(═O)B, —C(═O)CR 3A R 3B B, —CO 2 B, —C(═S)OB, —CONR 3C B, —C(═S)NR 3C B, a hydrogen atom, or the like, wherein A 1 and A 2 are not both hydrogen atoms, wherein B is an optionally substituted 3- to 12-membered monocyclic or polycyclic heterocyclic group, an optionally substituted 3- to 12-membered cyclic amino group, or a group represented by the following formula (B), wherein the 3- to 12-membered monocyclic or polycyclic heterocyclic group and the 3- to 12-membered cyclic amino group have at least one or more secondary nitrogen atoms in the ring; R 1 is a hydrogen atom or the like; R 2A , R 2B , R 2C , and R 2D are identical or different, and each independently a hydrogen atom or the like; and R 8 is alkyl. wherein * denotes a bonding position.