- Photochemical synthesis method of heteroarylamine compounds
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The invention provides a photochemical synthesis method of heteroarylamine compounds. The photochemical synthesis method comprises the following steps: S1, mixing raw materials including heteroaryl nitro compounds, a solvent and a photocatalyst to obtain a mixture; and S2, carrying out a photocatalytic reduction reaction on the mixture under an illumination condition to obtain a product system containing the heteroarylamine compounds. According to the photochemical synthesis method, photocatalytic reduction of various different heteroaryl nitro compounds is achieved under the illumination condition, and the high-yield heteroaryl amine compounds are obtained. The photocatalyst is an existing common catalyst, has no strict requirements on equipment and is easy to recover, and the safety riskof the heteroarylamine compound and the catalyst cost are reduced. Any metal reagent and reducing agent do not need to be added in the whole reaction process of photocatalysis, the reaction conversion rate is high, and post-treatment is simple and easy to operate, so the method is safer and more environmentally friendly.
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Paragraph 0068
(2020/10/14)
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- Design, synthesis and in vitro cytotoxic activity of new 6,9-disubstituted purine analogues
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A series of new 6,9-disubstituted purine analogs with 4-substituted piperazine at C-6 and 4-substituted benzyl at N-9 were designed and synthesized in four steps. All synthesized compounds (7-26) were screened initially for their in vitro anticancer activity on Huh7 liver, HCT116 colon and MCF7 breast carcinoma cell lines. Cytotoxic bioactivity studies revealed that all compounds screened, with compound 19 being the exception, were found to have promising cytotoxic activities at IC50 range of 0.05-21.8 μM against cancer cells Huh7, HCT116 and MCF7. Among the prepared purine analogs, two of them (12 and 22) exhibited excellent cytotoxic activities, with IC50 0.08-0.13 μM, on Huh7 cells comparable to camptothecin (CPT) and better than cladribine, fludarabine and 5-FU. Afterwards, the evaluation of cytotoxicity of the most potent purine analogs was screened against further hepatocellular cancer (HCC) cell lines. The 6-(4-(4-trif-luoromethylphenyl)piperazine (12) and 6-(4-(3,4-dichlorophenyl)piperazine analogs (25) displayed a significant IC50 values (IC50 0.1-0.13 μM) comparable to CPT and better cytotoxic bioactivity when compared with 5-FU, cladribine and fludarabine on HCC cells (Huh7 and HepG2).
- Atalay, Rengul Cetin,Guven, Ebru Bilget,Kucukdumlu, Asligul,Tuncbilek, Meral
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- Preparation method for catalyzing pyrimidine cyclic hydroxyl chlorination by tetraethylammonium chloride
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The invention discloses a preparation method for catalyzing pyrimidine cyclic hydroxyl chlorination by tetraethylammonium chloride, which comprises the following steps: (1) adding phosphorus oxychloride into a container, adding tetraethylammonium chloride as a catalyst, adding a pyrimidine cyclic hydroxyl compound, and heating to react; (2) preparing an alkali liquor, cooling to 0 DEG C, and slowly dropwise adding an obtained reaction liquid into the alkali liquor for quenching to obtain a target product. The method has the advantages that the provided pyrimidine cyclic hydroxyl chlorination catalysis method is small in environmental pollution, the obtained product is light in color, the catalysis efficiency is high, and the phosphorus oxychloride recovery pressure is small.
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Paragraph 0028-0031
(2020/04/17)
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- Synthesis and herbicidal evaluation of aryloxyphenoxypropiona te derivatives containing purine moiety
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series of purinoxyphenoxypropionates were designed and synthesized by introducing 8-(trifluoromethyl)-9H-purine into the aryloxyphenoxypropionate backbone. Methods: The products were characterized by 1H NMR and HRMS. Results and Conclusion: Preliminary bioassays indicated that most of the compounds exhibited good herbicidal activity at 200 mg/L.
- Shi, Jianjun,Ren, Guihua,Dai, Zhimeng,Wu, Ningjie,Weng, Jianquan,Xu, Tianming,Liu, Xinghai,Tan, Chengxia
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- Synthesis and biological evaluation of novel 6,11-dihydro-5H-benzo[e]pyrimido- [5,4-b][1,4]diazepine derivatives as potential c-Met inhibitors
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Over expression of c-Met tyrosine kinase is known to promote tumorigenesis and metastasis, as well as to cause therapeutic resistance. Herein a series of novel 6,11-dihydro-5H-benzo[e]pyrimido[5,4-b][1,4]diazepine derivatives were designed, synthesised and evaluated for their c-Met kinase inhibition. Compounds 17e, 17f, 18a, and 18b were further examined for their anti-proliferative activities against four typical cancer cell lines (PC-3, Panc-1, HepG2, and Caki-1). The promising compound 17f was identified as a multi-target receptor tyrosine kinase inhibitor, which also displayed favourable pharmacokinetic properties in rats, had an acceptable safety profile in preclinical studies, and significant anti-tumour activity in the Caki-1 tumour xenograft model.
- Huang, Daowei,Huang, Lei,Zhang, Qingwei,Li, Jianqi
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p. 212 - 228
(2017/09/23)
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- 1-SUBSTITUTED 1,2,3,4-TETRAHYDRO-1,7-NAPHTHYRIDIN-8-AMINE DERIVATIVES AND THEIR USE AS EP4 RECEPTOR ANTAGONISTS
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The present invention provides a compound represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof has an EP4 receptor antagonistic action, and is useful as an agent for the prophylaxis or treatment of EP4 receptor associated diseases (e.g., rheumatoid arthritis, aortic aneurysm (e.g. abdominal aortic aneurysm, thoracic aortic aneurysm, thoracoabdominal aortic aneurysm etc.), endometriosis, ankylosing spondylitis, inflammatory breast cancer etc.) and the like.
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Paragraph 0290
(2017/02/09)
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- CYCLIC DI-NUCLEOTIDE COMPOUNDS AND METHODS OF USE
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Disclosed are cyclic-di-nucleotide cGAMP analogs, methods of synthesizing the compounds, pharmaceutical compositions comprising the compounds thereof, and use of compounds and compositions in medical therapy.
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Paragraph 0218
(2017/10/11)
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- Development of dichloroacetamide pyrimidines as pyruvate dehydrogenase kinase inhibitors to reduce cancer cell growth: Synthesis and biological evaluation
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Pyruvate dehydrogenases kinases (PDKs) have recently emerged as an attractive target for anticancer treatment. Herein, we report the synthesis and biological evaluation of novel PDK1 inhibitors as anticancer agents. Of the newly synthesized compounds, N-(4,6-bis(4-(2-hydroxyacetyl)piperazin-1-yl)-2-methylpyrimidin-5-yl)-2,2-dichloroacetamide (40) is found to inhibit the growth of SF188 cancer cells with an IC50 value of 8.21 M. Isothermal titration calorimetry (ITC) experiments reveal that compound 40 directly binds to PDK1 with a Kd value of 14.7 M. Compound 40 inhibits PDK1 activity by 72.5% at a concentration of 40 , meaning it could be a useful compound to explore the pharmacology of PDK1.
- Zhang, Shao-Lin,Zhang, Wen,Xiao, Qingpin,Yang, Zheng,Hu, Xiaohui,Wei, Zhiyi,Tam, Kin Yip
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p. 78762 - 78767
(2016/09/09)
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- IRAK INHIBITORS AND USES THEREOF
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The present invention provides compounds, compositions thereof, and methods of using the same.
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Paragraph 00297; 00298; 00299
(2015/04/15)
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- PROCESS FOR THE PREPARATION OF AN INTERMEDIATE FOR A TRIAZOLOPYRIMIDINE CARBONUCLEOSIDE
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A process for the preparation of 4,6-dihalopyrimidin-5-amines of formula (II), or salts thereof, which comprises reacting 5-aminopyrimidin-4,6-diols of formula (III), or salts thereof, or a solvate either of the compound of formula (III) or of a salt thereof, with a halogenating agent, new intermediates useful in the preparation of the compound of formula (II) and processes for the preparation of these intermediates. The invention also refers to a process for the preparation of ticagrelor or a pharmaceutically acceptable salt thereof from 4,6-dihalo-2-(propylthio)pyrimidin-5-amine of formula (IIA).
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Paragraph 0160 - 0162
(2015/06/10)
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- A PROCESS FOR THE PREPARATION OF AN INTERMEDIATE FOR A TRIAZOLOPYRIMIDINE CARBONUCLEOSIDE
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A process for the preparation of 4,6-dihalopyrimidin-5-aminesof formula (II), or salts thereof, which comprises reacting 5-aminopyrimidin-4,6-diols of formula (III), or salts thereof, or a solvate either of the compound of formula (III) or of a salt thereof, with a halogenating agent, new intermediates useful in the preparation of the compound of formula (II) and processes for the preparation of these intermediates. The invention also refers to a process for the preparation of ticagrelor or a pharmaceutically acceptable saltthereoffrom 4,6-dihalo-2- (propylthio)pyrimidin-5-amine of formula (IIA).
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Page/Page column 33; 34
(2014/03/21)
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- HETEROCYCLIC COMPOUNDS AND USES THEREOF
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Compounds and pharmaceutical compositions of formulae (I), (XI) and (XII) as PI3 kinase modulators and their use in the treatment of diseases such as cancer.
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Paragraph 00531
(2013/03/26)
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- HETEROCYCLIC COMPOUNDS AND USES THEREOF
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Compounds and pharmaceutical compositions that modulate kinase activity, including PI3 kinase activity, and compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including PI3 kinase activity, are described herein.
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Page/Page column 81
(2012/05/21)
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- An efficient method for aryl nitro reduction and cleavage of azo compounds using iron powder/calcium chloride
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A novel, efficient Fe/CaCl2 system is revealed for the reduction of nitroarenes and reductive cleavage of azo compounds by catalytic transfer hydrogenation (CTH). The selective reduction of nitro compounds in the presence of sensitive functional groups including halides, carbonyl, hydroxyl, aldehyde, methyl, methoxy, acetyl, nitrile, and ester substituents with an excellent yields is reported. The simple experimental procedure and easy purification make the protocol advantageous
- Chandrappa,Vinaya,Ramakrishnappa,Rangappa
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experimental part
p. 3019 - 3022
(2011/03/17)
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- Synthesis of [14C]-, [13C4]-, and [ 13C4, 15N2]-5-amino-4-iodopyrimidine
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5-Amino-4-iodopyrimidine labeled with either carbon-14 or with the stable isotopes carbon-13 and nitrogen-15 was prepared starting from commercially available labeled diethylmalonate and formamide. This compound is a useful intermediate for carbon-nitrogen and carbon-carbon bond formations. Copyright
- Latli, Bachir,Jones, Paul-James,Krishnamurthy, Dhileepkumar,Senanayake, Chris H.
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- INHIBITORS OF IAP
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The invention provides novel inhibitors of IAP that are useful as therapeutic agents for treating malignancies where the compounds having the general formula U1 - M - U2 wherein M is a linking group covalently joining R2, R3, R4 or R5 of U1 to an R2, R3, R4 or R5 group of U2; U1 and U2 have the general formula (I) and G, X1, X2, R2, R3, R3', R4, R4' and R5, are as described herein.
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Page/Page column 83
(2008/12/08)
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- Aryl nitro reduction with iron powder or stannous chloride under ultrasonic irradiation
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The selective reduction of aryl nitro compounds in the presence of sensitive functionalities, including halide, carbonyl, nitrile, and ester substituents, under ultrasonic irradiation at 35 kHz is reported in yields of 39-98%. Iron powder proved superior to stannous chloride with high tolerance of sensitive functional groups and high yields of the desired aryl amines in relatively short reaction times. Simple experimental procedure and purification also make the iron reduction of aryl nitro compounds advantageous over other methods of reduction. Copyright Taylor & Francis Group, LLC.
- Gamble, Allan B.,Garner, James,Gordon, Christopher P.,O'Conner, Sean M. J.,Keller, Paul A.
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p. 2777 - 2786
(2008/02/12)
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- INHIBITORS OF IAP
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The invention provides novel inhibitors of IAP that are useful as therapeutic agents for treating malignancies where the compounds have the general formula (I): wherein Q, X1, X2, Y, Z1, Z2, Z3, Z4, R1, R2, R3, R3', R4, R4', R5, R6, R6' and n are as described herein.
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Page/Page column 59
(2008/06/13)
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- Dinucleotide-analogous tetrapeptides. Specific triplex formation with complementary polynucleotides
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Several tetrapeptides (1-4) having two adenyl moieties at the side chains interacted complementary base-specifically with poly (dT) or poly (U). The hypochromic effects and CD spectra of the complexes suggested the formation of triplexes, which are more stable than those between natural ApA and the polynucleotides.
- Yamazaki, Takahisa,Komatsu, Kazunori,Umemiya, Hiroki,Hashimoto, Yuichi,Shudo, Koichi,Kagechika, Hiroyuki
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p. 8363 - 8366
(2007/10/03)
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