rel-2-[(5aR,11bR)-2,6-dioxo-3,5а,6,11b-tetrahydro-2Н,5Н-chromeno[4′,3′:4,5]thiopyrano[2,3-d]thiazol-5а-yl]acetic acid

• 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: rel-2-[(5aR,11bR)-2,6-dioxo-3,5а,6,11b-tetrahydro-2Н,5Н-chromeno[4′,3′:4,5]thiopyrano[2,3-d]thiazol-5а-yl]acetic acid
• 英文别名: 2-[(1S,10S)-9,15-dioxo-8-oxa-12,16-dithia-14-azatetracyclo[8.7.0.02,7.013,17]heptadeca-2,4,6,13(17)-tetraen-10-yl]acetic acid
• 化学式: C₁₅H₁₁NO₅S₂
• 分子量: 349.388
• InChiKey: WWOHJZXAWSYQOP-BMIGLBTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  143
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  rel-2-[(5aR,11bR)-2,6-dioxo-3,5а,6,11b-tetrahydro-2Н,5Н-chromeno[4′,3′:4,5]thiopyrano[2,3-d]thiazol-5а-yl]acetic acid 、 对氨基苯酚 在 溶剂黄146 作用下， 反应 10.0h， 以40%的产率得到rel-(6′R,7′R)-7′-(2-hydroxyphenyl)-1-(4-hydroxyphenyl)-3′,7′-dihydro-2H,2′H,5H-spiro[pyrolidin-3,6′-thiopyrano[2,3-d]thiazol]-2,2′,5-trione
  参考文献：
  名称：

  Synthesis and antitrypanosomal activity of new 6,6,7-trisubstituted thiopyrano[2,3-d][1,3]thiazoles

  摘要：

  A series of novel 6,6,7-trisubstituted thiopyrano[2,3-d][1,3]thiazoles-based molecules have been synthesized and evaluated as potential antitrypanosomal agents. The most active analogue 3b inhibited Trypanosoma brucei brucei and Trypanosoma brucei gambiense with an IC50 of 0.26 and 0.42 mu M, respectively. They could be considered as potent hits for further antitrypanosomal drug discovery efforts. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.091
• 作为产物：
  描述：

  衣康酸 、 5-(2-hydroxybenzylidene)-4-thioxo-2-thiazolidinone 在 溶剂黄146 、 对苯二酚 作用下， 反应 2.0h， 以45%的产率得到rel-2-[(5aR,11bR)-2,6-dioxo-3,5а,6,11b-tetrahydro-2Н,5Н-chromeno[4′,3′:4,5]thiopyrano[2,3-d]thiazol-5а-yl]acetic acid
  参考文献：
  名称：

  Synthesis and antitrypanosomal activity of new 6,6,7-trisubstituted thiopyrano[2,3-d][1,3]thiazoles

  摘要：

  A series of novel 6,6,7-trisubstituted thiopyrano[2,3-d][1,3]thiazoles-based molecules have been synthesized and evaluated as potential antitrypanosomal agents. The most active analogue 3b inhibited Trypanosoma brucei brucei and Trypanosoma brucei gambiense with an IC50 of 0.26 and 0.42 mu M, respectively. They could be considered as potent hits for further antitrypanosomal drug discovery efforts. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.091

文献信息

• trans -Aconitic acid-based hetero -Diels-Alder reaction in the synthesis of thiopyrano[2,3- d ][1,3]thiazole derivatives
  作者：Nataliya Zelisko、Olexandr Karpenko、Volodymyr Muzychenko、Andrzej Gzella、Philippe Grellier、Roman Lesyk

  DOI：10.1016/j.tetlet.2017.03.062

  日期：2017.5

  hetero-Diels-Alder reaction of 5-arylideneisorhodanines with trans-aconitic acid proceeds as a regio- and diastereoselective process with spontaneous decarboxylation of the [4+2]-adduct to furnish thiopyrano[2,3-d][1,3]thiazole (2) and chromeno[4′,3′:4,5]thiopyrano[2,3-d]thiazole (3) derivatives analogously to the use of itaconic acid as a dienophile. Conversely, the one-pot, three-component reaction of 5-ar

  5-芳基异二十二碳四烯酸与反式-乌头酸的异-狄尔斯-阿尔德反应是区域和非对映选择性过程，其中[4 + 2]加合物自发脱羧生成噻喃并[2,3- d ] [1,3类似于使用衣康酸作为亲双烯体，]噻唑（2）和苯并[4'，3'：4,5]巯基吡喃并[2,3- d ]噻唑（3）衍生物。相反，5-arylideneisorhodanines，一锅，三组分反应反式-aconitic酸和苯胺进行时没有脱羧，从而导致新的相对- （5' - [R，6' - [R，7' - [R）-5'-羧基7'-芳基的1-芳基-3'，7'-二氢-2 ħ，2 ' ħ，5 ħ -螺[吡咯烷3,6'噻喃并[2,3- d ]噻唑] -2,2'，5-三酮4。有趣的是，使用的反式导致区域选择性相反-aconitic羧酸三甲酯，得到的rel - （5 - [R，6小号，7小号）-5- methyloxycarbonylmethyl -2-氧代-7-芳基-3
• 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
• Synthesis and antitrypanosomal activity of new 6,6,7-trisubstituted thiopyrano[2,3-d][1,3]thiazoles
  作者：Nataliya Zelisko、Dmytro Atamanyuk、Olexandr Vasylenko、Philippe Grellier、Roman Lesyk

  DOI：10.1016/j.bmcl.2012.09.091

  日期：2012.12

  A series of novel 6,6,7-trisubstituted thiopyrano[2,3-d][1,3]thiazoles-based molecules have been synthesized and evaluated as potential antitrypanosomal agents. The most active analogue 3b inhibited Trypanosoma brucei brucei and Trypanosoma brucei gambiense with an IC50 of 0.26 and 0.42 mu M, respectively. They could be considered as potent hits for further antitrypanosomal drug discovery efforts. (C) 2012 Elsevier Ltd. All rights reserved.