5-methyl-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4',3':4,5]thiopyrano-[2,3-d]thiazole-2,6-dione

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: 5-methyl-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4',3':4,5]thiopyrano-[2,3-d]thiazole-2,6-dione
• 英文别名: (1R,10S,11S)-11-methyl-8-oxa-12,16-dithia-14-azatetracyclo[8.7.0.02,7.013,17]heptadeca-2,4,6,13(17)-tetraene-9,15-dione
• 化学式: C₁₄H₁₁NO₃S₂
• 分子量: 305.378
• InChiKey: IOUGDLVGAMVLPG-JUWDTYFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  水杨醛 在 溶剂黄146 、 对苯二酚 作用下， 反应 2.33h， 生成 5-methyl-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4',3':4,5]thiopyrano-[2,3-d]thiazole-2,6-dione 、 5-methyl-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4',3':4,5]thiopyrano-[2,3-d]thiazole-2,6-dione
  参考文献：
  名称：

  Crotonic, cynnamic, and propiolic acids motifs in the synthesis of thiopyrano[2,3-d][1,3]thiazoles via hetero-Diels–Alder reaction and related tandem processes

  摘要：

  Various novel thiopyrano[2,3-d][1,3]thiazol-2-one-6-carboxylic acids derivatives were synthesized in 54-86% yields via hetero-Diels Alder reactions and related acylation-based tandem processes of 5-arylidene-4-thioxo-2-thiazolidinones with crotonic, propiolic, and cynnamic acids derivatives. Stereo- and regioselectivity of cycloaddition were investigated. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.083

文献信息

• Thiopyrano[2,3-d]thiazole structures as promising scaffold with anticancer potential
  作者：Nataliya Finiuk、Nataliya Zelisko、Olga Klyuchivska、Ihor Yushyn、Andrii Lozynskyi、Alina Cherniienko、Nazar Manko、Juliya Senkiv、Rostyslav Stoika、Roman Lesyk

  DOI：10.1016/j.cbi.2022.110246

  日期：2022.12

  Seven chromeno[4′,3':4,5]thiopyrano[2,3-d]thiazole derivatives were synthesized and screened for their cytotoxic effects on different lines of mammalian leukemia, breast adenocarcinoma, glioblastoma, and pseudo-normal and normal cells. The derivative 3 demonstrated toxicity towards tumor cells of Jurkat, K562, U251, HL-60, MCF-7, and MDA-MB-231 lines. At the same time, this compound possessed low toxicity

  合成了七种铬烯[4',3':4,5]吡喃并[2,3- d ]噻唑衍生物，并筛选了它们对哺乳动物白血病、乳腺癌、胶质母细胞瘤以及假正常和正常细胞的不同细胞系的细胞毒性作用. 衍生物3显示出对 Jurkat、K562、U251、HL-60、MCF-7 和 MDA-MB-231 系肿瘤细胞的毒性。同时，该化合物对细胞具有低毒性（IC 50  > 100 μM），用作对照，代表非肿瘤体细胞：HaCaT、HEK293 细胞以及鼠 Balb/c 3T3 和 J774.2 细胞，水貂 Mv1Lu 细胞和正常有丝分裂原激活的人血淋巴细胞。衍生物3诱导人白血病Jurkat T细胞和胶质母细胞瘤U251细胞凋亡通过线粒体依赖性途径和抑制 DNA 修复酶 PARP-1。该化合物引发 Jurkat 和 U251 细胞的促凋亡形态学变化，即染色质浓缩、细胞核碎裂和膜起泡。然而，与肿瘤 Jurkat 和 U251 细