Molecular design, synthesis and anticancer activity of new thiopyrano[2,3-d]thiazoles based on 5-hydroxy-1,4-naphthoquinone (juglone)

化学 阿霉素 立体化学 效力 1,4-萘醌 胡桃醌 细胞毒性T细胞 IC50型 噻唑 生物化学 体外 化疗 药物化学 内科学 医学
作者
Iryna Ivasechko,Andrii Lozynskyi,Julia Senkiv,Piotr Roszczenko,Yuliia Kozak,Nataliya Finiuk,Olga Klyuchivska,Nataliya Kashchak,Nazar Manko,Zvenyslava Maslyak,Danylo Lesyk,Andriy Karkhut,Svyatoslav Polovkovych,Robert Czarnomysy,Olga Szewczyk,Andriy Kozytskiy,Olexandr Karpenko,Dmytro Khyluk,Andrzej Gzella,Krzysztof Bielawski,Anna Bielawska,Petr Dzubak,Sona Gurska,Marian Hajduch,Rostyslav Stoika,Roman Lesyk
出处
期刊:European Journal of Medicinal Chemistry 卷期号:252: 115304-115304
标识
DOI:10.1016/j.ejmech.2023.115304
摘要

A series of 11-substituted 9-hydroxy-3,5,10,11-tetrahydro-2H-benzo[6,7]thiochromeno[2,3-d][1,3]thiazole-2,5,10-triones 3.1–3.13 were synthesized via hetero-Diels-Alder reaction of 5-ene-4-thioxo-2-thiazolidinones and 5-hydroxy-1,4-naphthoquinone (juglone). The structure of newly synthesized compounds was established by means of spectral data and a single-crystal X-ray diffraction analysis. The synthesized compounds were tested on a panel of cell lines representing different types of cancer as well as normal and pseudonormal cells and peripheral human blood lymphocytes. Compound 3.10 was found to be the most active derivative, exhibiting a cytotoxic effect similar to doxorubicin's one (IC50 ranged from 0.6 to 5.98 μM), but less toxic to normal and pseudonormal cells. All synthesized compounds were able to interact with DNA, although their anticancer activity did not correlate with the potency of interaction with DNA. The status of p53 in colorectal cancer cells correlated with the activity of the synthesized derivatives 3.1, 3.7, and 3.10. Compound 3.10 did not have an acute toxic effect on the body of С57BL/6 mice, unlike the well-known anticancer drug doxorubicin, which was used as a positive control. The injection of 3.10 (20 mg/kg) to mice had no effect on the counts of leukocytes, erythrocytes, platelets and hemoglobin level in their blood, in contrast to doxorubicin, which caused anemia and leukopenia, indicating bio-tolerance of 3.10 in vivo.
最长约 10秒,即可获得该文献文件

科研通智能强力驱动
Strongly Powered by AbleSci AI
更新
PDF的下载单位、IP信息已删除 (2025-6-4)

科研通是完全免费的文献互助平台,具备全网最快的应助速度,最高的求助完成率。 对每一个文献求助,科研通都将尽心尽力,给求助人一个满意的交代。
实时播报
1秒前
Ultraman45发布了新的文献求助10
1秒前
1秒前
蒋紫妍发布了新的文献求助10
3秒前
chaos发布了新的文献求助10
3秒前
青鸟完成签到,获得积分10
4秒前
kylin发布了新的文献求助10
4秒前
4秒前
4秒前
今天吃什么呢完成签到 ,获得积分10
5秒前
汉堡包应助科研鸟采纳,获得10
5秒前
年轻的凡雁完成签到,获得积分10
5秒前
榴莲发布了新的文献求助10
6秒前
orixero应助小时候采纳,获得10
6秒前
SciGPT应助张姚采纳,获得10
6秒前
Mumu发布了新的文献求助10
6秒前
落后凝莲发布了新的文献求助10
7秒前
8秒前
8秒前
Aries发布了新的文献求助10
9秒前
凯睿完成签到,获得积分10
9秒前
路路发布了新的文献求助10
9秒前
11秒前
拉普兰Z发布了新的文献求助10
11秒前
12秒前
美丽大方发布了新的文献求助100
12秒前
徐小徐发布了新的文献求助20
12秒前
guozao应助阿海采纳,获得10
13秒前
量子星尘发布了新的文献求助10
13秒前
chaos完成签到,获得积分20
15秒前
曾纪诚发布了新的文献求助10
15秒前
16秒前
1111完成签到,获得积分10
18秒前
姚琛完成签到 ,获得积分10
18秒前
shinysparrow应助高高黄豆采纳,获得100
21秒前
萧布发布了新的文献求助200
21秒前
小高宽度完成签到,获得积分10
22秒前
华仔应助科研通管家采纳,获得10
22秒前
ding应助科研通管家采纳,获得10
22秒前
老阎应助科研通管家采纳,获得30
22秒前
高分求助中
A new approach to the extrapolation of accelerated life test data 1000
Picture Books with Same-sex Parented Families: Unintentional Censorship 700
ACSM’s Guidelines for Exercise Testing and Prescription, 12th edition 500
Nucleophilic substitution in azasydnone-modified dinitroanisoles 500
不知道标题是什么 500
Indomethacinのヒトにおける経皮吸収 400
Phylogenetic study of the order Polydesmida (Myriapoda: Diplopoda) 370
热门求助领域 (近24小时)
化学 材料科学 医学 生物 工程类 有机化学 生物化学 物理 内科学 纳米技术 计算机科学 化学工程 复合材料 遗传学 基因 物理化学 催化作用 冶金 细胞生物学 免疫学
热门帖子
关注 科研通微信公众号,转发送积分 3976235
求助须知:如何正确求助?哪些是违规求助? 3520399
关于积分的说明 11203166
捐赠科研通 3256989
什么是DOI,文献DOI怎么找? 1798580
邀请新用户注册赠送积分活动 877738
科研通“疑难数据库(出版商)”最低求助积分说明 806516