- EFFECT OF HIGH PRESSURE ON THE RATE CONSTANT OF THE DIELS-ALDER REACTION BETWEEN FURAN AND MALEIC ANHYDRIDE
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The effect of high pressure (up to 700 MPa) on the rate of the Diels-alder reaction between furan and maleic anhydride has been investigated in deuterated acetone at 20 deg C.The volume effect of the reaction at atmospheric pressure is found to be ΔV
- Zhulin, V. M.,Kel'tseva, M. V.,Bogdanov, V. S.,Koreshkov, Yu. D.,Kabotyanskaya, E. B.
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- Stereoselective synthesis of 3,4,5,6-tetrahydroxycyclohexyl β-amino acid derivatives
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Stereoselective syntheses of racemic (1S,2R,3R,4R,5S,6R)- and (1S,2R,3R,4S,5S,6R)-3,4,5,6-tetrahydroxy derivatives of 2-aminocyclohexanecarboxylic acid have been achieved by a stereospecific Diels-Alder reaction between furan and maleic anhydride, a Curtius rearrangement and hydroxylation reactions.
- Chola, Joshua,Masesane, Ishmael B.
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- Antimicrobial activities of phosphonium containing polynorbornenes
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In this study, amphiphilic polyoxanorbornene with different alkyl and aromatic phosphonium side chains was synthesized. The biological activities of these polymers were determined by the minimal inhibitory concentration (MIC) against E. coli, S. aureus, M. tuberculosis and the yeast C. albicans, and cytotoxicity studies on red blood cells were performed. A series of polymers with different alkyl and aromatic substituents (methyl, ethyl, tripropyl, tert-butyl, phenyl, and tris 4-methoxyphenyl) and two types different molecular weight, 3000 g mol-1 and 10 000 g mol-1, were prepared. It was observed that the biological activity of the polymers with aromatic group substituents had an MIC of 16, 8, 64 and 128 μg mL-1 against E. coli, S. aureus, M. tuberculosis and C. albicans, respectively, while those with non-aromatic carbons had a higher MIC compared to those with aromatic carbons. The aromaticity of the repeat unit had impressive effects on hemolytic activities as well. Zeta potential measurements of E. coli incubated with active and inactive polymer concentration revealed a relationship between the MIC and membrane surface charge density. Polymers bearing aromatic groups killed the bacteria with widespread damage after the polymers, holding the threshold concentration, were added to the bacteria.
- Süer, N. Ceren,Demir, Ceren,ünübol, Nihan A.,Yal?in, ?zlem,Kocag?z, Tanil,Eren, Tarik
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- EFFECT OF HIGH PRESSURE ON THE COMPOSITION OF STEREOISOMERS OF THE DIELS-ALDER REACTION BETWEEN FURAN AND MALEIC ANHYDRIDE
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The kinetic data on the Diels-Alder reaction between furan and maleic anhydride at atmospheric pressure and 20 and 40 deg C correspond to a scheme of the process which includes transformation of an endo-isomer into an exo-isomer without preliminary decomp
- Zhulin, V. M.,Bogdanov, V. S.,Kel'tseva, M. V.,Kabotyanskaya, E. B.,Koreshkov, Yu. D.
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- Hierarchical preferences of hydroxylated oxanorbornane-based achiral amphiphiles
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Achiral amphiphiles with hydroxylated oxanorbornane headgroups showed specific morphological characteristics and hierarchical preferences depending upon the nature of lipophilic units. Detailed scanning electron microscopic (SEM) studies showed that twist
- Janni, D. Sirisha,Manheri, Muraleedharan K.
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Read Online
- A simple route for the synthesis of novel norcantharimide derivatives via acidolysis with hydrochloric acid(gas)
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In this work, seven new norcantharimide derivatives were synthesized by an acidolysis method. The compounds were prepared by acidolyzing trans-1,4-diacetate and trans-1,2-chloroacetate structures, which were obtained by stereospecific cleavage of the internal etheric bond of the tricyclic imides. The HCl(gas) was produced from the reaction of H2SO4 with NaCl. The resulting gas was bubbled into the reaction mixture. Trans-1,4-diacetate and trans-1,2-chloroacetate were thus acidolyzed, and the corresponding diol and halohydrin products were obtained respectively in moderate overall yields from low-cost starting materials, using simple and easily scalable chemistry. The products were characterized by means of spectroscopic techniques. The synthesized compounds have high potential as anticancer agents and can be valuable for studies in this area.
- K?se, Aytekin
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p. 1171 - 1178
(2021/03/08)
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- Cyclohexanedicarboxylic acid derivative with bridge ring and pharmaceutical composition and application thereof
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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.
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Paragraph 0081-0085
(2021/11/10)
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- The Wittig bioconjugation of maleimide derived, water soluble phosphonium ylides to aldehyde-tagged proteins
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Herein we disclose the transformation of maleimides into water-soluble tris(2-carboxyethyl)phosphonium ylides and their subsequent application in the bioconjugation of protein- and peptide-linked aldehydes. The new entry into Wittig bioconjugate chemistry proceeds under mild conditions and relies on highly water soluble reagents, which are likely already part of most biochemists' inventory. This journal is
- Asbjarnarson, Arni,Gudjonsson, Thorarinn,Hartmann, Rafael W.,Helgudottir, Hildur Run,Lehmann, Fredrik,Nilvebrant, Johan,Nygren, Per-?ke,Odell, Luke R.,Pijnappel, Matthijs,Traustadottir, Gunnhildur Asta
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supporting information
p. 10417 - 10423
(2021/12/17)
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- Synthesis of l-ascorbic acid-amino acid-norcantharidin conjugates and their biological activity evaluation in vitro
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Three components of L-ascorbic acid, amino acid and functionalized norcantharidins were constructed together in several steps to form 42 norcantharidin derivatives in a high yield. The structure of these synthesized l-ascorbic acid-amino acid-norcantharidin conjugates are determined by 1HNMR, 13CNMR and MS spectrum. The results showed that compounds 6e, 6g, 6j, 6l, 6m, 6b, 6e, 6i, and 6n showed high cytotoxicity to HepG2 and compounds 6b, 6e-g, 6l, 6n, 7b, 7d, 7h, 7i, 7n, 8g, 8i exhibited high cytotoxicity to SW480; Meanwhile, besides 6b, 6e, 6g, and 6k, the other compounds showed less toxic to LO2 at a concentration of 50 μg/mg after 72 h. Compound 6g can induce Mφ-type macrophages derived from mouse bone marrow to polarize to M1-type macrophages.
- Wang, Xianheng,Wu, Caoyuan,Zhang, Jidong,Zhao, Changkuo,Zhou, Yiqi
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- Supramolecular chemistry under mechanochemical conditions: A small molecule template generated and integrated into a molecular-to-supramolecular and back-to-molecular cascade reaction
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We describe the integration of a small-molecule hydrogen-bond-donor template into a cascade reaction that is comprised of a combination of molecular and supramolecular events. The cascade is performed mechanochemically and in the presence of μL amounts of
- MacGillivray, Leonard R.,Swenson, Dale C.,Yelgaonkar, Shweta P.
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p. 3569 - 3573
(2020/04/15)
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- Inverse Electron-Demand Diels-Alder Bioconjugation Reactions Using 7-Oxanorbornenes as Dienophiles
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Oligonucleotides, peptides, and peptide nucleic acids incorporating 7-oxanorbornene as a dienophile were reacted with tetrazines linked to either a peptide, d-biotin, BODIPY, or N-acetyl-d-galactosamine. The inverse electron-demand Diels-Alder (IEDDA) cycloaddition, which was performed overnight at 37 °C, in all cases furnished the target conjugate in good yields. IEDDA reactions with 7-oxanorbornenes produce a lower number of stereoisomers than that of IEDDA cycloadditions with other dienophiles.
- Agramunt, Jordi,Ginesi, Rebecca,Grandas, Anna,Pedroso, Enrique
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p. 6593 - 6604
(2020/07/14)
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- Norcantharidin carboxylic acid trifluorobenzyl ester as well as synthesis method and application thereof
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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.
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Paragraph 0039-0041
(2020/07/02)
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- Synthesis and anti-tumor application of norcantharidin carboxylic acid difluorobenzyl ester
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The invention provides synthesis and anti-tumor application of norcantharidin carboxylic acid difluorobenzyl ester with a structural formula shown as I in the specification. The specific structure ofthe norcantharidin carboxylic acid difluorobenzyl ester as shown in the formula I is shown in the specification, and activity tests show that the norcantharidin carboxylic acid difluorobenzyl ester asshown in the formula I, which is designed and synthesized by the invention, is a suitable anti-tumor candidate drug, especially as a candidate anti-liver-cancer 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 norcantharidin carboxylic acid difluorobenzyl ester has the advantages that the raw materials are easy to obtain, and the operation and the implementation are very easy.
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Paragraph 0035-0037
(2020/07/13)
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- Tetrafluorobenzyl norcantharidin carboxylate and synthesis method thereof
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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.
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Paragraph 0040-0041
(2020/07/15)
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- Norcantharidin fluorine-containing benzyl ester salt derivative as well as synthesis method and anti-tumor application thereof
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The invention discloses a norcantharidin fluorine-containing benzyl ester salt derivative as well as a synthesis method and anti-tumor application thereof. The specific structure of the norcantharidinfluorine-containing benzyl ester salt derivative as shown in the formula I is shown in the specification, and activity tests show that the norcantharidin fluorine-containing benzyl ester salt derivative as shown in the formula I, which is designed and synthesized by the invention, is a suitable anti-tumor candidate drug, especially as an anti-liver cancer candidate drug. Compared with a positivecontrol drug norcantharidin, the norcantharidin sodium salt has the advantage that the water solubility, the stability and the anti-tumor activity are improved.
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Paragraph 0031; 0035-0036
(2020/06/20)
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- Camptothecin - hydroxyacetic acid - norcantharidin conjugate and application thereof
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The present invention provides camptothecin-hydroxyacetic acid-norcantharidin conjugates I: The dotted line I in Formula, represents that the bond on the position is saturated or unsaturated double bond ;R is selected from the group C1 - C6 of alkyl,substituted alkyl, cycloalkyl, benzyl or substituted benzyl ;R2 selected from hydrogen or halogen. activity tests prove, cost-effective I-target product yield high, and easy to prepare for, The method, of the present invention provides good antitumor effect . particularly liver cancer, stomach cancer I colon cancer and pancreatic cancer . The invention can be prepared by, % by weight of the synthesized camptothecin conjugate, according to the. present invention.
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Paragraph 0029-0031
(2020/03/17)
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- Homocam ptothecin 5-ene norcantharidin acid ester derivative, and regioselective synthesis method thereof
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The invention discloses a homocam ptothecin 5-ene norcantharidin acid ester derivative represented by fomula I, and a regioselective synthesis method thereof, wherein R is selected from C1-C6 alkyl, substituted alkyl, and cycloalkyl. It is confirmed by activity test that the homocam ptothecin 5-ene norcantharidin acid ester derivative I possesses excellent anti-tumor effect, and is especially highin inhibition activity on liver cancer, stomach cancer, colorectal carcinoma and pancreas cancer. According to the preparation method of the homocam ptothecin 5-ene norcantharidin acid ester derivative, the raw materials are easily available; cost is low; synthesis reaction regioselectivity is extremely high; target product yield is high; and preparation is convenient.
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Paragraph 0025-0029
(2019/11/21)
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- Homocamptothecin norcantharidinate derivative, and regioselective synthesis method thereof
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The invention provides a homocamptothecin norcantharidinate derivative I and a regioselective synthesis method thereof in the fields of design and synthesis of novel drugs. The homocamptothecin norcantharidinate derivative I has a structural formula as shown in a formula I which is described in the specification. In the formula I, R is selected from the group consisting of C1-C6 alkyl, substitutedalkyl and cycloalkyl groups. Activity test results prove that the homocamptothecin norcantharidinate derivative I designed and synthesized by using the method provided by the invention has good antitumor effect, and specifically has high activity on liver cancer, gastric cancer, colon cancer and pancreatic cancer. In addition, the method for preparing the homocamptothecin norcantharidinate derivative I provided by the invention has the advantages of easily-available raw materials, low cost, extremely-high synthesis reaction regioselectivity and high target product yield; and the homocamptothecin norcantharidinate derivative I provided by the invention is easy to be prepared.
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Paragraph 0025; 0028-0029
(2019/11/21)
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- Natural drug composition modified derivative and anti-tumor application thereof
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The invention discloses a camptothecin derivative I and a synthesis method thereof in the field of new drug design and synthesis. The structural formula of the camptothecin derivative I is as shown inthe specification, R in the formula I is selected from H, Br or dehydrogenation, and R1 is selected from C1-C3 alkyl, naphthenic base, benzyl and substituted benzyl. Activity tests prove that the designed and synthesized camptothecin derivative I has excellent anti-tumor effects and particularly is high in liver cancer, stomach cancer, colon cancer and pancreatic cancer activity.
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Paragraph 0022; 0023; 0024
(2019/04/17)
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- Tunable E- Z Photoisomerization in α,β-Peptide Foldamers Featuring Multiple (E/ Z)-3-Aminoprop-2-enoic Acid Units
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Systems in which an external stimulus elicits a response through some sort of modification at the molecular or supramolecular level bear potential for the development of smart materials and devices. This work describes a versatile synthetic approach suitable for the stepwise incorporation of multiple, even consecutive, units of the simplest Cα,β-unsaturated β-amino acid, (E/Z)-3-aminoprop-2-enoic acid, in peptide-based foldamers. The properties of these, including photoinduced E/Z isomerizations, were investigated.
- Marafon, Giulia,Crisma, Marco,Moretto, Alessandro
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supporting information
p. 4182 - 4186
(2019/06/04)
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- POTENTIALLY ANTICARCINOGENIC NOVEL ISOINDOLE-1,3-DIONE DERIVATIVES AND SYNTHESIS METHOD FOR SUCH COMPOUNDS
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The invention is related to novel isoindole-1,3-dione derivatives which are determined to be effective in vitro on certain cancer types (e.g., Lung, breast and cervical cancer) as well as the synthesis method of such compounds for use in the chemistry sector, pharmaceuticals industry and pharmacy sector.
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Page/Page column 8; 9
(2019/11/12)
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- Synthesis and biological evaluation of new chloro/acetoxy substituted isoindole analogues as new tyrosine kinase inhibitors
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We have developed a versatile synthetic approach for the synthesis of new isoindole derivatives via the cleavage of ethers from tricyclic imide skeleton compounds. An exo-cycloadduct prepared from the Diels–Alder reaction of furan and maleic anhydride furnished imide derivatives. The epoxide ring was opened with Ac2O or Ac2O/AcCl in the presence of a catalytic amount of H2SO4 in order to yield new isoindole derivatives 8a-d and 9a-d. The anticancer activity of these compounds was evaluated against the HeLa cell lines. The synthesized compounds showed inhibitory effects on the viability of HeLa cells and the degree of cytotoxicity was increased with the level of bigger branched isoindole derivatives. To better understand the acting mechanism of these molecules, western blot analysis was performed with using mTOR and its downstream substrates. In addition, human mTOR and ribozomal S6 kinase β1 (RS6Kβ1) have been investigated with molecular modelling studies as possible targets for compound series 8 and 9.
- ?ahin, Ertan,?anl?-Mohamed, Gül?ah,Akdemir, Atilla,K?se, Aytekin,Kara, Yunus,Kaya, Meltem,Kishal?, Nurhan H.
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- Preparation method and application of D - valine-substituted norcantharidin derivative containing pyridazinone structure
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The invention discloses a preparation method of a D-valine substituted norcantharidin derivative containing a pyridazinone structure as well as an application thereof. The method comprises the following steps: 1,3-dipolar cycloaddition is used for introducing pyrazole rings to C5 and C6 positions in a D-valine substituted norcantharidin structure, and the material and chromonic aldehyde hydrazonecontaining a pyridazinone structure are reacted and the pyridazinone structure is introduced. The derivative has a plurality of biological activities and is used for development and research of latentmedicament.
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Paragraph 0011; 0026
(2019/08/20)
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- Remarkable Reactivity of Boron-Substituted Furans in the Diels-Alder Reactions with Maleic Anhydride
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The reactivity of boron-substituted furans as dienes in the Diels-Alder reaction with maleic anhydride has been investigated. Gratifyingly, the furans with boryl substituents at C-3 gave the exo cycloadduct exclusively with excellent yields. In particular, the potassium trifluoroborate exhibited outstanding reactivity at room temperature. Theoretical calculations suggested that the trifluoroborate group is highly activating and also that the thermodynamics is the main factor that determines whether the products can be obtained efficiently or not.
- Medrán, Noelia S.,Dezotti, Federico,Pellegrinet, Silvina C.
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supporting information
p. 5068 - 5072
(2019/07/03)
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- Homocam ptothecin 5, 6-dibromo norcantharidin acid ester derivative, and regioselective synthesis method thereof
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The invention belongs to the field of new drug design and synthesis, and discloses a homocam ptothecin 5, 6-dibromo norcantharidin acid ester derivative represented by fomula I, and a regioselective synthesis method thereof, wherein R is selected from C1-C6 alkyl, substituted alkyl, and cycloalkyl. It is confirmed by activity test that the homocam ptothecin 5, 6-dibromo norcantharidin acid ester derivative I possesses excellent anti-tumor effect, and is especially high in inhibition activity on liver cancer, stomach cancer, colorectal carcinoma and pancreas cancer. According to the preparationmethod of the homocam ptothecin 5, 6-dibromo norcantharidin acid ester derivative, the raw materials are easily available; cost is low; synthesis reaction regioselectivity is extremely high; target product yield is high; and preparation is convenient.
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Paragraph 0027; 0030-0031
(2019/11/21)
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- A fullerene helical peptide: synthesis, characterization and formation of self-assembled monolayers on gold surfaces
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The synthesis of a C60-peptide using “clickable” fullerene and peptide derivatives is described. The peptide is composed of a repeating sequence of α-aminoisobutyric acid (Aib) and two l-alanine (Ala) residues, promoting the formation of a helical conformation, which has been confirmed by IR absorption, NMR and circular dichroism measurements. In addition, the presence of a lipoyl moiety, at the end of the peptide sequence, allows the formation of self-assembled monolayers of the C60-peptide and the parent peptide on a gold surface. A C60-alkyl derivative was also prepared to compare the self-assembly properties of fullerene derivatives containing peptides or alkyl chains. The fullerene assembly on a gold substrate characterized by quartz crystal microbalance and by cyclic voltammetry show that the monolayers containing alkyl chains are slightly less well packed than the peptide monolayers. Finally, polarization modulation reflection adsorption infra-red spectroscopy measurements indicate that the C60-peptide tends to be more vertical than the parent peptide which could originate from complementary C60-C60 and helical-helical interactions.
- Nasrallah, Houssein,Rabah, Jad,Bui-Thi-Tuyet, Van,Baczko, Krystyna,Fensterbank, Hélène,Bourdreux, Flavien,Goncalves, Anne-Marie,Declerck, Valérie,Boujday, Souhir,Humblot, Vincent,Wright, Karen,Vallée, Anne,Allard, Emmanuel
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supporting information
p. 19423 - 19432
(2018/12/13)
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- RELEASABLE CONJUGATES
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The present application provides compounds of Formula (B), or pharmaceutically acceptable salts thereof, wherein D is a residue of a biologically active drug, which underdo hydrolysis under physiological conditions to release the biologically active drug and which are useful in the treatment of disorders that could be beneficially treated with the drug.
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Page/Page column 193; 194
(2018/09/28)
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- Preparation method of L-phenylalanine substituted norcantharidin derivative containing pyridazinone structure and application
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The invention discloses a preparation method of a L-phenylalanine substituted norcantharidin derivative containing a pyridazinone structure and application. According to the preparation method, parazole rings are introduced to C5 and C6 in an L-phenylalanine substituted norcantharidin structure by using a 1,3-dipolar cycloaddition method, further a pyridazinone structure is introduced through a reaction with chromone aldehyde hydrazone containing a pyridazinone structure, and the prepared derivative has multiple biological activities and has the potential of medicine development and study.
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Paragraph 0027
(2018/03/24)
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- Preparation method and application of D-aminocarproic acid substituted norcantharidin derivative containing pyridazinone structure
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The invention discloses a preparation method and application of a D-aminocarproic acid substituted norcantharidin derivative containing a pyridazinone structure. The preparation method has the advantages that pyrazole rings are introduced into C5 and C6 sites in the D-phenylalanine substituted norcantharidin structure by a 1,3-dipolar cycloaddition method; then, reaction with chromone hydrazone containing the pyridazinone structure is performed, so that the pyridazinone structure is introduced; the prepared derivative has various biological activities and is applied to potential medicine development and study.
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Paragraph 0027
(2018/04/03)
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- Synthesis and structure-activity relationship study of novel 3-heteroarylcoumarins based on pyridazine scaffold as selective MAO-B inhibitors
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Compounds of hybrid structure pyridazine-coumarin were discovered as potent, selective and reversible inhibitors of monoamine oxidase B (MAO-B). These compounds were synthesized in good yield following a multistep approach based on Knoevenagel reaction and using as key intermediate pyridazinone 16, which was obtained from maleic anhydride and furan. Compounds 9b and 9d are the most active compounds of these series, with IC50 values in the sub-micromolar range, and lack of cytotoxic effects. Theoretical calculation of ADME properties also suggested a good pharmacokinetic profile for both compounds. Docking simulations provided insights into enzyme inhibitor interactions and allowed us to rationalize the observed structure-activity relationships (SARs).
- Costas-Lago, María Carmen,Besada, Pedro,Rodríguez-Enríquez, Fernanda,Vi?a, Dolores,Vilar, Santiago,Uriarte, Eugenio,Borges, Fernanda,Terán, Carmen
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supporting information
p. 1 - 11
(2017/08/10)
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- Diacetylene-Based C 2h-Symmetric Monomers for Two-Dimensional-Polymer Synthesis
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Two linear monomers with two terminal photoreactive groups (anthracene or maleimide) embedded in a diacetylene skeleton were synthesized for two-dimensional-polymer synthesis. Both of them were crystallized and their single-crystal structures were solved. It was found that the size of terminal groups can be critical for diacetylene's arrangement. The crystal structure of dimaleimide monomer revealed that maleimide groups strongly stacking in antiparallel and the photo-induced [2+2] cycloaddition of stacked maleimides was preliminary studied.
- Song, Mengyao,Ma, Hanbing,Ren, Minghan,Ai, Zhaoquan,Li, Ming
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supporting information
p. 445 - 450
(2017/02/24)
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- Synthesis and anticancer activity evaluation of new isoindole analogues
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We have developed a versatile synthetic approach for the synthesis of new isoindole derivatives via the cleavage of ethers from tricyclic imide skeleton compounds. An exo-cycloadduct prepared from the Diels–Alder reaction of furan and maleic anhydride furnished imide derivatives. The epoxide ring was opened with Ac2O in the presence of a catalytic amount of H2SO4 in order to yield new isoindole derivatives (8a and 8b). The anticancer activity of these compounds was evaluated against MCF-7 (breast adenocarcinoma) and A549 (adenocarcinomic human alveolar basal epithelial) cell lines. The synthesized compounds showed concentration- and time-dependent inhibitory effects on the viability of both cell lines. Compound 8a was more toxic compared to 8b in both cancer cell lines, having higher cytotoxicity against A549 cells. Testing the toxicity properties of these compounds on the BEAS 2B (human bronchial epithelial) cell line indicated that while both compounds decreased the cell viability of cancer cells, they were less toxic on healthy lung cells. Microscopy images of A549 cells after treatment with the new isoindole derivatives displayed characteristic apoptotic morphology compared to BEAS 2B cells. The results demonstrated here suggest that these new compounds might be considered as possible potential anticancer agents for the treatment of lung and breast cancer.
- K?se, Aytekin,Bal, Y?ld?z,Kishal?, Nurhan H.,?anl?-Mohamed, Gül?ah,Kara, Yunus
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p. 779 - 786
(2017/03/06)
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- A new synthon for the synthesis of aminoinositol derivatives
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The regio- and stereoselective synthesis of a new synthon, trans-3,8-dioxatricyclo[3.2.1.02,4]octane-6,7-diamine, from 7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate is reported. Transformation of the acid functionalities to acyl azides followed by Curtius rearrangement gave the corresponding trans-diisocyanate, which was reacted with HCl to produce a trans-diamino compound that is a potentially important synthon for the versatile synthesis of aminocyclitols.
- Cokol, Nalan Korkmaz,Kaya, Serdal,Balci, Metin
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supporting information
p. 2732 - 2735
(2017/06/23)
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- 5. 6 - double-dehydrogenation to a spot maomao mellow derivative and its anti-tumor application
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The invention provides a 5, 6-bidehydronorcantharides alcohol derivative and application thereof to tumor resistance. The 5, 6-bidehydronorcantharides alcohol derivative has the structural formula as shown in the formula I as described in the description, wherein R is selected from -H or -CH2COOH. Activity tests prove that the 5, 6-bidehydronorcantharides alcohol derivative I designed and synthesized by the invention has a favorable anti-hepatoma effect and is expected to be applied as an antitumor cantharidin drug in clinic. In addition, the novel synthesis method for the compound has the advantages of available raw materials, low cost, simple synthesis route, high yield and convenience in operation and implementation.
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Paragraph 0032-0035
(2017/08/24)
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- Albumin-polymer conjugate nanoparticles and their interactions with prostate cancer cells in 2D and 3D culture: Comparison between PMMA and PCL
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Using proteins as the hydrophilic moiety can dramatically improve the biodegradability and biocompatibility of self-assembled amphiphilic nanoparticles in the field of nanomedicine. In this study, we fabricated and evaluated curcumin loaded albumin-polycaprolactone nanoparticles as a novel drug delivery system for prostate carcinoma therapeutics and compared their performance to poly(methyl methacrylate) (PMMA), a non-degradable and amorphous polymer. The maleimide functionalized poly(ε-caprolactone) (PCL) was obtain using ring opening polymerization (ROP) of ε-caprolactone where N-(2-hydroxyethyl)maleimide was used as an initiator. The resorbable albumin-polymer conjugate was prepared by conjugating the hydrophobic maleimide-terminated PCL to the hydrophilic bovine serum albumin (BSA) via a simple Michael addition reaction. PMMA was conjugated in a similar manner. The amphiphilic BSA-polymer conjugates can self-assemble into nanoparticles, displaying well-defined structure, prolonged storage stability, and excellent biocompatibility. The BSA nanoparticles, with encapsulated curcumin, exhibited highly enhanced antitumor activity compared to free curcumin. Furthermore, the high efficacy of the curcumin loaded nanoparticles was verified by effectively inhibiting the growth of three-dimensional LNCaP multicellular tumour spheroids. The cytotoxicity was attributed to the efficient cellular uptake of the nanoparticles through caveolic endocytosis. The direct comparison between PCL and the PMMA revealed that drug loading and release as well as cytotoxicity is not significantly affected by the nature of the polymer. However, it seems that nanoparticles based on PMMA penetrate quicker into LNCaP multicellular tumour spheroids thanks to the increased stability. The faster penetration was found to reduce the toxicity of the nanoparticles as evidenced by the lower number of dead cells. In contrast, the fully degradable PCL-based nanoparticles were more efficient in delivering the drug, thus limiting the growth of LNCaP multicellular tumour spheroids.
- Jiang, Yanyan,Lu, Hongxu,Dag, Aydan,Hart-Smith, Gene,Stenzel, Martina H.
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p. 2017 - 2027
(2016/03/22)
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- Norcantharidin monomer-acid monoester derivative and anti-tumor application thereof
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The invention provides a norcantharidin monomer-acid monoester derivative and an application thereof. The structural formula of the derivative is shown as the No.3 formula (please see the specification), wherein R is selected from alkyl or benzyl of C1 to C3. An activity test proves that the third designed and synthesized norcantharidin monomer-acid monoester derivative has good inhabitation activity in liver cancer tumor cells, stomach cancer tumor cells and colon cancer tumor cells, and can be expected to be applied to preparing medicine for resisting the three tumors.
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Paragraph 0027; 0029; 0030
(2017/07/19)
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- Containing chromon structure-isoxazole Norcantharidin derivative and its preparation method and application
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The invention discloses novel chromone structure containing isoxazole norcantharidin derivatives as well as a preparation method and an application thereof. The preparation method is characterized by introducing isoxazole rings to C5 and C6 in a norcantharidin structure by using a 1,3-dipolar cycloaddition method to react with chromone derivatives to import the chromone structures, thus synthesizing a series of totally six novel chromone structure containing isoxazole norcantharidin derivatives. The isoxazole norcantharidin derivatives are applied to synthesis of antitumor drugs and have broad application prospects.
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Paragraph 0020; 0032-0033
(2017/02/02)
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- NOVEL LIPOPHILIC N-SUBSTITUTED NORCANTHARIMIDE DERIVATIVES AND USE THEREOF
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PROBLEM TO BE SOLVED: To provide novel N-substituted norcantharimide derivatives that exhibit excellent selective cytotoxicity to cancerous cells. SOLUTION: The N-substituted norcantharimide derivatives are represented by formula (I). EFFECT: The N-substituted norcantharimide derivatives are useful as lead compounds for producing pharmaceutical compositions for treating cancer, particularly leukemia. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPO&INPIT
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Paragraph 0064; 0065
(2017/04/03)
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- NOVEL LIPOPHILIC N-SUBSTITUTED NORCANTHARIMIDE DERIVATIVES AND USES THEREO
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Novel N-substituted norcantharimide derivatives are disclosed herein. The novel N-substituted norcantharimide derivatives are useful as lead compounds for manufacturing a medicament or a pharmaceutical composition for treating cancer, particularly for treating leukemia.
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Paragraph 0069-0072; 0073; 0074
(2017/04/28)
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- Palladium-Catalyzed [2+1] Cycloadditions Affording Vinylidenecyclopropanes as Precursors of 7-Membered Carbocycles
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Palladium(II) acetate in association with secondary phosphine oxides provides an efficient catalytic system for [2+1] cycloadditions starting from oxanorbornene derivatives and tertiary propargyl esters giving rise to vinylidenecyclopropanes. This reaction is specific to bidentate phosphinito-phosphinous acid ligands generated from secondary phosphine oxides. The [2+1] cycloaddition was found broad in scope with a high tolerance to various functional groups. Moreover, vinylidenecyclopropanes were straightforwardly converted into oxabicyclo[3.2.1]oct-2-ene derivatives through a palladium-catalyzed ring-expansion. Finally, the oxa bridge cleavage of oxatricyclic compounds yields functionalized 7-membered carbocycles.
- Lepronier, Aymeric,Achard, Thierry,Giordano, Laurent,Tenaglia, Alphonse,Buono, Gerard,Clavier, Herve
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supporting information
p. 631 - 642
(2016/02/27)
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- Acid-sensitive camptothecin-site 20 norcantharidate derivative and antineoplastic application thereof
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The invention provides a camptothecin-site 20 norcantharidate derivative with a structural formula as shown in I which is described in the specification, and a preparation method and antineoplastic application thereof. Results of activity test prove that the camptothecin-site 20 norcantharidate derivative as shown in I is an appropriate candidate antineoplastic drug, especially a candidate drug for resisting liver cancers, stomach cancers and colorectal cancers. Compared with positive contrast drugs, i.e., camptothecin and cantharidin, the camptothecin-site 20 norcantharidate derivative has improved water solubility and stability; and the camptothecin-site 20 norcantharidate derivative is sensitive to acid and can be easily hydrolyzed. Moreover, the preparation method for the camptothecin-site 20 norcantharidate derivative employs easily available raw materials, has high yield and is easy to operate and implement.
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Paragraph 0028; 0033; 0034
(2017/01/31)
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- Norcantharidin composite salt derivative and its anti-tumor application (by machine translation)
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This invention has offered a kind of Norcantharidin composite salt derivative, its structural formula such as formula 11 is shown, Wherein M and M1 independently selected from the group consisting of positive univalent or divalent cation, and M and M1 is a divalent cation is asynchronous. Active test proves that, this invention is designed and synthesized Norcantharidin of the composite salt derivative 11 and two kinds of colon cancer to liver cancer has good inhibition activity, is expected to be applied to the preparation of the above-mentioned two kinds of anti-tumor drug. (by machine translation)
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Paragraph 0029; 0030; 0031
(2017/04/18)
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- Unsaturated norcantharidin benzyl ester barium salt and antitumor applications thereof
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The present invention provides an unsaturated norcantharidin benzyl ester barium salt derivative I and applications thereof, wherein the structural formula is represented by a formula I, and the formula I is defined in the specification. According to the present invention, the activity test results prove that the designed and synthesized unsaturated norcantharidin benzyl ester barium salt I has good inhibition activity on liver cancer cells at a low concentration so as to be expected to be applied in preparation of anti-hepatoma drugs.
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Paragraph 0021; 0022
(2017/05/02)
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- 5,6-double-dehydrogenation norcantharidin ethyl ester barium salt derivative and anti-tumor application thereof
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The invention provides a 5,6-double-dehydrogenation norcantharidin ethyl ester barium salt derivative I and application thereof. The structural formula of the derivative I is shown in the formula I (please see the formula I in the specification). The activity test proves that the designed and synthesized 5,6-double-dehydrogenation norcantharidin ethyl ester barium salt I has good inhibitory activity to liver cancer tumor cells at low concentration, and is expected to be applied to preparation of anti-liver-cancer drugs.
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Paragraph 0025; 0026
(2017/10/27)
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- Bromo Norcantharidin monoacid diethlyl and its preparation method and application
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The invention discloses bromo-norcantharidin ethyl gallate, namely 5,6-dibromo norcantharidin ethyl gallate, wherein the structural formula of bromo-norcantharidin ethyl gallate is as shown in the formula I. As is proven by activity tests, bromo-norcantharidin ethyl gallate, namely open-cycle 5,6-dibromo norcantharidin ethyl gallate has a good anti-heptoma effect and can be used as an efficient and low-toxic cantharidin antineoplastic drug. The selectivity of a preparation process is good, raw materials are easy to obtain, the cost is low, the synthetic route is simple, the method is convenient to operate and conduct, toxicity of a product obtained through synthesis is low, the bromo-norcantharidin ethyl gallate is safe, the yield is high, and the purity is high. Therefore, the process has the characteristics of high efficiency, convenience and low cost.
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Paragraph 0027-0029
(2018/02/04)
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- Bromo Norcantharidin simple acid animal pen ester and its synthetic method and application
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The invention discloses a bromo-norcantharidin acid-benzyl ester shown as a structural formula I. The bromo-norcantharidin acid-benzyl ester is an open-loop 5,6-dibromo-norcantharidin acid benzyl ester, and an active test proves that the bromo-norcantharidin acid-benzyl ester has a good anti-liver-cancer effect and can be used as a high-efficiency and low-toxicity cantharidin anticancer medicine The synthesis process is excellent in selectivity, raw materials are readily available, the cost is low, the synthetic route is simple, operation is easy, a product obtained by the synthesis has low toxicity, high yield and high purity, and the process is high-efficiency, convenient and low in cost.
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Paragraph 0024-0027
(2018/01/19)
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- Synthesis and extraction studies with a rationally designed diamide ligand selectIVe to actinide(IV) pertinent to the plutonium uranium redox extraction process
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A new class of conformationally constrained oxa-bridged tricyclo-dicarboxamide (OTDA) ligand was rationally designed for the selective extraction of tetravalent actinides pertinent to the Plutonium Uranium Redox EXtraction (PUREX) process. Two of the designed diamide ligands were synthesized and extraction studies were performed for Pu(iv) from HNO3 medium. The mechanism of extraction was investigated by studying various parameters such as feed HNO3, NaNO3 and OTDA concentrations. The nature of the extracted species was found to be [Pu(NO3)4(OTDA)]. One of the OTDA ligands was elaborately tested and showed the selective extraction of Pu(iv) and Np(iv) over other actinide species, viz., U(vi), Np(v), Am(iii), lanthanides and fission products contained in a nuclear waste from the PUREX process. DFT calculations predicted the charge density on each of the coordinating 'O' atoms of OTDA supporting its high Pu(iv) selectivity over other ions studied and also provided the energy optimized structure of OTDA and its Pu(iv) complex.
- Sharma, Shikha,Panja, Surajit,Bhattacharyya, Arunasis,Dhami, Prem S.,Gandhi, Preetam M.,Ghosh, Sunil K.
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supporting information
p. 7737 - 7747
(2016/05/24)
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- ANTICANCER AGENTS AND PROCESS OF MAKING THEREOF
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Provided herein are compositions and processes of making of anticancer compounds useful for cancer treatments. These cyclohexenone compounds show an unexpected result against certain cancer cells compared to their known analogs.
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Paragraph 0151-0152
(2016/09/12)
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- Protein transduction domains mimics
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The invention generally relates to synthetic mimics of cell penetrating peptides. More particularly, the invention relates to certain novel monomers, oligomers and polymers (e.g., co-polymers) that are useful for the preparation of synthetic mimics of cell penetrating peptides, their compositions, preparations and use.
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Page/Page column 33
(2016/08/07)
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- A pyrromonazole Norcantharidin derivative and its preparation method and application
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The invention discloses a pyrazol norcantharidin derivative of a chromone structure, and a preparation method and an application of the derivative. The preparation method comprises the following steps: introducing a pyrazol ring into the positions of C5-C6 in a norcantharidin structure by using a 1,3-dipolar cycloaddition method, reacting with a chromone derivative, and introducing into a chromone structure, thereby synthesizing a series of pyrazol norcantharidin derivatives of the chromone structure, wherein the number of the derivatives is 6 in all, and the activity of norcantharidin is improved. The pyrazol norcantharidin derivative of the chromone structure, which is disclosed by the invention, is wide in application prospect when being applied to synthesis of anti-tumor medicines.
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Paragraph 0039
(2016/10/10)
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- Glucoside-containing structured triazole norcantharidin derivative as well as preparation method and application thereof
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The invention discloses a glucoside-containing structured triazole norcantharidin derivative as well as a preparation method and application thereof. The preparation method comprises the following steps: introducing 1,2,3-triazole into sites C5 and C6 in a norcantharidin structure by using a 1,3-dipolar cycloaddition method, enabling 1,2,3-triazole to react with 1-nitrine-acetyl-alpha-D-glucose, and introducing a glucoside structure, thereby synthesizing the glucoside-containing structured triazole norcantharidin derivative. The compound has multiple biological activities, and can be used for preparing anti-tumor medicines.
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Paragraph 0031; 0032
(2017/01/26)
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- L-leucine substituted norcantharidin derivative and preparation method and application
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The invention discloses an L-leucine substituted norcantharidin derivative and a preparation method and application thereof. The method is characterized in that pyrazol rings are introduced into sites C5 and C6 in a L-leucine substituted norcantharidin structure through a 1,3-dipole cycloaddition method to react with a chromone derivative to be guided into a chromone structure, and the pyrazol L-leucine substituted norcantharidin derivative containing the chromone structure is synthesized. The derivative has the good inhibiting effect on tumor cell strains, has the good inhibition ratio and selectivity on leukemia cells, and has the good industrial application prospect on the aspect of anti-tumor drug preparation.
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Paragraph 0022; 0028; 0029
(2017/02/17)
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- D-phenylalanine substituted norcantharidin derivative as well as preparation method and application thereof
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The invention discloses a D-phenylalanine substituted norcantharidin derivative as well as a preparation method and application thereof. The D-phenylalanine substituted norcantharidin derivative as well as the preparation method and application thereof are characterized in that pyrazole rings are introduced to C5 potential and C6 potential in a D-phenylalanine substituted norcantharidin structure by a 1,3-dipolar cycloaddition method, the pyrazole rings and a chromone derivative react so that a chromone structure is guided, and a pyrazole D-phenylalanine substituted norcantharidin derivative containing the chromone structure is synthesized. The derivative has a favorable effect of restraining tumor cell strains, has higher suppression ratio and better selectivity for leukemic cells, and has excellent industrial application prospects in the respects of preparing antitumor drugs and the like.
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Paragraph 0031; 0032
(2017/04/14)
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- Lactoside structure containing triazole norcantharidin derivative, preparation method therefor and application of lactoside structure containing triazole norcantharidin derivative
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The invention discloses a lactoside structure containing triazole norcantharidin derivative, a preparation method therefor and an application of the lactoside structure containing triazole norcantharidin derivative. According to the preparation method, the lactoside structure containing 1,2,3-triazole norcantharidin derivative is synthesized through introducing 1,2,3-triazole to C5 and C6 bits of a structure of norcantharidin by a 1,3-dipole cycloaddition method, and carrying out a reaction with 1-azido-peracetyl lactose to introduce a lactoside structure. The compound has diversified biological activities and can be applied to the preparation of antitumor drugs.
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Paragraph 0033; 0034
(2017/04/21)
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