29745-04-8Relevant articles and documents
Structural studies on cycloadducts of furan, 2-methoxyfuran, and 5-trimethylsilylcyclopentadiene with maleic anhydride and N-methylmaleimide
Yit, Wooi Goh,Pool, Brett R.,White, Jonathan M.
, p. 151 - 156 (2008)
(Chemical Equation Presented) The early stages of the retro-Diels-Alder reaction are clearly apparent in the structures of the cycloadducts formed between furan or 5-trimethylsilylcyclopentadiene with maleic anhydride and N-methylmaleimide. The degree of lengthening of the C-C bonds that break in this reaction is clearly related to the known reactivity of these cycloadducts toward this reaction. In the structures of the cycloadducts 21 and 22 derived from 2-methoxyfuran, the early stages of an alternative fragmentation reaction are apparent, consistent with the reactivity of these compounds in solution.
Crystal structures of (3R,3aR,4S,7R,7aS)-3-(allyloxy)hexahydro-4,7- epoxyisobenzofuran-1(3H)-one and (3S,3aR,4S,7R,7aS)-3-((E)-but-2-en-1-yloxy) hexahydro-4,7-epoxyisobenzofuran-1(3H)-one: Confirmation of NMR predicted stereocentre geometry
Tarleton, Mark,Bernhardt, Paul V.,McCluskey, Adam
, p. 639 - 644 (2012)
Crystal structures of two isomeric norcantharidin derivatives (3R,3aR,4S,7R,7aS)-3-(allyloxy)hexahydro-4,7-epoxyisobenzofuran-1(3H)-one (7b), and (3S,3aR, 4S,7R,7aS)-3-((E)-but-2-en-1-yloxy)hexahydro-4,7- epoxyisobenzofuran- 1(3H)-one (8a) have been determined. In both instances the equivalent enantiomer was also obtained. The crystal structures of these compounds clarify the stereochemistry inferred only by NMR analysis before. Springer Science+Business Media, LLC 2012.
Synthesis and anticancer activity of a series of norcantharidin analogues
Tarleton, Mark,Gilbert, Jayne,Sakoff, Jennette A.,McCluskey, Adam
, p. 573 - 581 (2012)
Cantharidin (1) and norcantharidin (2) display high levels of anticancer activity against a broad range of tumour cell lines. Synthetic manipulation of norcantharidin yields (3S,3aR,4S,7R,7aS)-3-hydroxyhexahydro-4,7- epoxyisobenzofuran-1(3H)-one (3), which also displays a high level of anticancer activity against tumour cells but interestingly, shows selectivity towards HT29 (colon; GI50 = 14 μM) and SJ-G2 (glioblastoma; GI50 = 15 μM) cell lines. Substitution at the hydroxyl group of the cyclic lactone within (3) produces a diasteromeric pair of products that have no difference in cytotoxicity over the cell lines tested. Incorporation of an isopropyl tail at this position (16) produced the most promising compound of this series to date, with strong selectivity towards HT29 (colon; GI50 = 19 μM) and SJ-G2 (glioblastoma; GI50 = 21 μM) cell lines but completely void of any activity against the remaining tumour cell lines (GI50 > 100 μM), as per the parent molecule. We also discovered that the introduction of a terminal phosphate moiety (28) at the same position produced a different trend in cytotoxicity with strong activity in BE2-C (neuroblastoma; GI 50 = 9 μM) cells; suggestive of an alternate mode of action.
Cyclohexanedicarboxylic acid derivative with bridge ring and pharmaceutical composition and application thereof
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Paragraph 0081-0083; 0100-0101, (2021/11/10)
The invention discloses a cyclohexane dicarboxylic acid derivative with a bridged ring represented by general formula (I). The application of the stereoisomers and the pharmaceutically acceptable salts in the preparation of antitumor drugs has obvious inhibition effects on leukemia, liver cancer, lung cancer, gastric cancer and ovarian cancer. The compound disclosed by the invention has high anti-tumor activity, wide anti-tumor spectrum and low toxicity, and is suitable for preparing anti-cancer drugs.
Norcantharidin carboxylic acid trifluorobenzyl ester as well as synthesis method and application thereof
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Paragraph 0043-0045, (2020/07/02)
A norcantharidin carboxylic acid trifluorobenzyl ester as well as a synthesis method and application thereof are provided. The specific structure of the norcantharidin carboxylic acid trifluorobenzylester as shown in the formula I is shown in the specification. Activity tests show that the norcantharidin carboxylic acid trifluorobenzyl ester as shown in the formula I is a suitable anti-tumor candidate drug, especially as an anti-liver cancer candidate drug. Compared with positive control drugs norcantharidin and sodium norcantharidate, the water solubility, the stability and the anti-tumor activity are improved. In addition, the synthesis method of the norcantharidin carboxylic acid trifluorobenzyl ester has the advantages that the raw materials are easy to obtain, and the operation and the implementation are very easy.
Tetrafluorobenzyl norcantharidin carboxylate and synthesis method thereof
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Paragraph 0042-0043, (2020/07/15)
The invention discloses tetrafluorobenzyl norcantharidin carboxylate and a synthesis method thereof. The structural formula is shown as a formula I, the specific structure of tetrafluorobenzyl norcantharidin carboxylate shown in a formula I is shown in the specification and the synthesis method comprises the following steps that side-chain tetrafluorobenzyl alcohol (compound 5) and norcantharidin(compound 4) undergo a reaction in an organic solvent at a certain temperature under the action of an organic alkali to obtain tetrafluorobenzyl norcantharidin carboxylate shown as a formula I. The synthesis route is shown as follows that: carboxyl is introduced into the molecular structure of the compound disclosed by the invention, so that the water solubility and stability are improved, and dueto the introduction of a fluorine-containing group, the physical property, the chemical property and the biological activity of parent molecules can be remarkably changed, so that the pharmacokineticefficacy can be enhanced. In addition, the raw materials of the synthesis method are easy to obtain, and operation and implementation are very easy.
