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不对称取代二苯并[][1,5]二氮杂环辛烷-6,12(5,11)-二酮——生物活性分子设计的一种便捷骨架。

Unsymmetrically Substituted Dibenzo[][1,5]-diazocine-6,12(5,11)dione-A Convenient Scaffold for Bioactive Molecule Design.

机构信息

Institute of Biochemistry and Biophysics, Polish Academy of Sciences, Pawińskiego 5a, 02-106 Warsaw, Poland.

Biological and Chemical Research Centre, University of Warsaw, Żwirki i Wigury 101, 02-089 Warsaw, Poland.

出版信息

Molecules. 2020 Feb 18;25(4):906. doi: 10.3390/molecules25040906.

DOI:10.3390/molecules25040906
PMID:32085499
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7070320/
Abstract

A novel approach for the synthesis of unsymmetrically substituted dibenzo[][1,5]diazocine-6,12(5,11)diones has been developed. This facile three-step method uses variously substituted 1-benzo[][1,3]oxazine-2,4-diones (isatoic anhydrides) and 2-aminobenzoic acids as a starting materials. The obtained products were further transformed into -alkyl-, -acetyl- and dithio analogues. Developed procedures allowed the synthesis of unsymmetrical dibenzo[][1,5]diazocine-6,12(5,11)diones and three novel heterocyclic scaffolds: benzo[]naphtho[2,3-][1,5]diazocine-6,14(5,13)dione, pyrido[3,2-][1,5]benzodiazocine-5,11(6,12)-dione and pyrazino[3,2-][1,5]benzodiazocine-6,12(5,11)dione. For 11 of the compounds crystal structures were obtained. The preliminary cytotoxic effect against two cancer (HeLa, U87) and two normal lines (HEK293, EUFA30) as well as antibacterial activity were determined. The obtained dibenzo[][1,5]diazocine(5,11)6,12-dione framework could serve as a privileged structure for the drug design and development.

摘要

一种合成不对称取代的二苯并[][1,5]二氮杂环庚烷-6,12(5,11)二酮的新方法已经开发出来。这种简便的三步法使用各种取代的 1-苯并[][1,3]恶嗪-2,4-二酮（异氰酸酐）和 2-氨基苯甲酸作为起始原料。所得产物进一步转化为 -烷基-、-乙酰基和二硫代类似物。所开发的方法允许不对称二苯并[][1,5]二氮杂环庚烷-6,12(5,11)二酮和三个新的杂环骨架的合成：苯并[]萘并[2,3-][1,5]二氮杂环庚烷-6,14(5,13)二酮、吡啶并[3,2-][1,5]苯并二氮杂环庚烷-5,11(6,12)-二酮和吡嗪并[3,2-][1,5]苯并二氮杂环庚烷-6,12(5,11)二酮。其中 11 种化合物的晶体结构已得到确定。测定了对两种癌细胞（HeLa、U87）和两种正常细胞（HEK293、EUFA30）的初步细胞毒性作用以及抗菌活性。所得到的二苯并[][1,5]二氮杂环庚烷(5,11)6,12-二酮骨架可以作为药物设计和开发的优势结构。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f74/7070320/650cecd52173/molecules-25-00906-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f74/7070320/d4e5fb23c34e/molecules-25-00906-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f74/7070320/54b77f180447/molecules-25-00906-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f74/7070320/aa7b6237d628/molecules-25-00906-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f74/7070320/35e040c52af1/molecules-25-00906-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f74/7070320/a1307a24f483/molecules-25-00906-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f74/7070320/3e0f40f23c99/molecules-25-00906-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f74/7070320/df881559fd74/molecules-25-00906-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f74/7070320/650cecd52173/molecules-25-00906-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f74/7070320/d4e5fb23c34e/molecules-25-00906-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f74/7070320/54b77f180447/molecules-25-00906-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f74/7070320/aa7b6237d628/molecules-25-00906-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f74/7070320/35e040c52af1/molecules-25-00906-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f74/7070320/a1307a24f483/molecules-25-00906-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f74/7070320/3e0f40f23c99/molecules-25-00906-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f74/7070320/df881559fd74/molecules-25-00906-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0f74/7070320/650cecd52173/molecules-25-00906-g004.jpg

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