- Visible Light-Induced Aerobic Epoxidation of α,β-Unsaturated Ketones Mediated by Amidines
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An aerobic photoepoxidation of α,β-unsaturated ketones driven by visible light in the presence of tetramethylguanidine (3b), tetraphenylporphine (H2TPP), and molecular oxygen under mild conditions was revealed. The corresponding α,β-epoxy ketones were obtained in yields of up to 94% in 96 h. The reaction time was shortened to 4.6 h by flow synthesis. The mechanism related to singlet oxygen was supported by experiments and density functional theory (DFT) calculations.
- Wu, Yufeng,Zhou, Guangli,Meng, Qingwei,Tang, Xiaofei,Liu, Guangzhi,Yin, Hang,Zhao, Jingnan,Yang, Fan,Yu, Zongyi,Luo, Yi
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p. 13051 - 13062
(2018/10/25)
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- Discovery of 5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine inhibitors of Erk2
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The discovery and optimization of a series of tetrahydropyridopyrimidine based extracellular signal-regulated kinase (Erks) inhibitors discovered via HTS and structure based drug design is reported. The compounds demonstrate potent and selective inhibition of Erk2 and knockdown of phospho-RSK levels in HepG2 cells and tumor xenografts.
- Blake, James F.,Gaudino, John J.,De Meese, Jason,Mohr, Peter,Chicarelli, Mark,Tian, Hongqi,Garrey, Rustam,Thomas, Allen,Siedem, Christopher S.,Welch, Michael B.,Kolakowski, Gabrielle,Kaus, Robert,Burkard, Michael,Martinson, Matthew,Chen, Huifen,Dean, Brian,Dudley, Danette A.,Gould, Stephen E.,Pacheco, Patricia,Shahidi-Latham, Sheerin,Wang, Weiru,West, Kristina,Yin, Jianping,Moffat, John,Schwarz, Jacob B.
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p. 2635 - 2639
(2014/06/09)
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- Discovery of 5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine inhibitors of Erk2
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The discovery and optimization of a series of tetrahydropyridopyrimidine based extracellular signal-regulated kinase (Erks) inhibitors discovered via HTS and structure based drug design is reported. The compounds demonstrate potent and selective inhibition of Erk2 and knockdown of phospho-RSK levels in HepG2 cells and tumor xenografts.
- Blake, James F.,Gaudino, John J.,De Meese, Jason,Mohr, Peter,Chicarelli, Mark,Tian, Hongqi,Garrey, Rustam,Thomas, Allen,Siedem, Christopher S.,Welch, Michael B.,Kolakowski, Gabrielle,Kaus, Robert,Burkard, Michael,Martinson, Matthew,Chen, Huifen,Dean, Brian,Dudley, Danette A.,Gould, Stephen E.,Pacheco, Patricia,Shahidi-Latham, Sheerin,Wang, Weiru,West, Kristina,Yin, Jianping,Moffat, John,Schwarz, Jacob B.
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p. 2635 - 2639
(2015/02/19)
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- Synthesis of novel strobilurin-pyrimidine derivatives and their antiproliferative activity against human cancer cell lines
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A series of new strobilurin-pyrimidine analogs were designed and synthesized based on the structures of our previously discovered antiproliferative compounds I and II. Biological evaluation with two human cancer cell lines (A549 and HL60) showed that most of these compounds possessed moderate to potent antiproliferative activity. Two potent candidates (8f, IC50 = 2.2 nM and 11d, IC50 = 3.4 nM) were identified with nanomolar activity against leukemia cancer cell line HL60 for further development. This activity represents a 1000- to 2500-fold improvement compared to the parent compounds I and II and is 20- to 30-fold better than the chemotherapy drug, doxorubicin. The present work provides strong incentive for further development of these strobilurin-pyrimidine analogs as potential antitumor agents for the treatment of leukemia.
- Chai, Baoshan,Wang, Shuyang,Yu, Wenquan,Li, Huichao,Song, Chuanjun,Xu, Ying,Liu, Changling,Chang, Junbiao
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p. 3505 - 3510
(2013/07/28)
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- Ligustrazine derivatives. Part 6: Design, synthesis and evaluation of novel ligustrazinyl acylguanidine derivatives as potential cardiovascular agents
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A series of novel Ligustrazinyl acylguanidines was designed, synthesized and evaluated for their protective effect on injured vascular endothelial cell (ECV-304). The preliminary results demonstrated that some compounds possessed more potent activities than that of Ligustrazine in stimulating replication of the injured endothelial cell. Among the active compounds, compounds 8b, 8f and 8l displayed remarkable antioxidative activity with low EC50 values of 0.097, 0.059 and 0.094 mM, respectively. Structure-activity relationships were briefly discussed.
- Li, Zhenyu,Yu, Fang,Zhan, Peng,Shen, Yuemao,Liu, Xinyong,Cui, Lei,Wang, Shouxun
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p. 928 - 933,6
(2020/08/31)
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- Discovery and initial optimization of 5,5′-disubstituted aminohydantoins as potent β-secretase (BACE1) inhibitors
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8,8-Diphenyl-2,3,4,8-tetrahydroimidazo[1,5-a]pyrimidin-6-amine (1) was identified through HTS, as a weak (micromolar) inhibitor of BACE1. X-Ray crystallographic studies indicate the 2-aminoimidazole ring forms key H-bonding interactions with Asp32 and Asp228 in the catalytic site of BACE1. Lead optimization using structure-based focused libraries led to the identification of low nanomolar BACE1 inhibitors such as 20b with substituents which extend from the S1 to the S3 pocket.
- Nowak, Pawel,Cole, Derek C.,Aulabaugh, Ann,Bard, Jonathan,Chopra, Rajiv,Cowling, Rebecca,Fan, Kristi Y.,Hu, Baihua,Jacobsen, Steve,Jani, Minakshi,Jin, Guixan,Lo, Mei-Chu,Malamas, Michael S.,Manas, Eric S.,Narasimhan, Rani,Reinhart, Peter,Robichaud, Albert J.,Stock, Joseph R.,Subrath, Joan,Svenson, Kristine,Turner, Jim,Wagner, Erik,Zhou, Ping,Ellingboe, John W.
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scheme or table
p. 632 - 635
(2010/06/12)
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- SUBSTITUTED 5,6-DIHYDRO-6-PHENYLBENZO[F] ISOQUINOLIN-2-AMINE COMPOUNDS
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The present invention relates to substituted 5,6-dihydro-6- phenylbenzo[f]isoquinolin-2-amine compounds and methods of synthesizing these compounds. The present invention also relates to pharmaceutical compositions containing substituted 5,6-dihydro-6-phenylbenzo[f]isoquinolin-2-amine compounds and methods of treating cell proliferative disorders, such as cancer, by administering these compounds and pharmaceutical compositions to subjects in need thereof.
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Page/Page column 148; 284
(2010/08/04)
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- Reaction of thiourea dioxides with amines
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The reaction mechanism of thiourea dioxides with ammonia and primary aliphatic amines involves direct nucleophile (ammonia or amine) reactions with thiourea dioxides, followed by dissociation of the resulting adduct to form the sulfoxylate ion. 2004 MAIK "Nauka/Interperiodica".
- Makarov,Kudrik,Terskaya,Davydov
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p. 1383 - 1385
(2007/10/03)
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- Process for producing N-phosphonomethylglycine acid
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The invention provides a process for producing N-phosphonomethylglycine acid (NPMG) comprising (a) oxidizing an N-(phosphonomethyl) iminodiacetic acid (NPMIDA) derivative of the general formula I STR1 wherein n is 1 or 2 and R5, R5', R6 and R6' are independently H, NH2, STR2 or an aryl, cycloalkyl or straight or branched chain alkyl or alkenyl group optionally substituted by hydroxy or halogen, or an alkylaryl group, provided that at least one of R5, R5 ', R6 or R6 ' is hydrogen, to produce a corresponding iminourea salt of NPMG and then (b) reacting the salt with an acid stronger than NPMG whereby NPMG is produced and there remains in solution the iminourea salt of the stronger acid.
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- Synthesis of Guanidino-1,3,5-triazines Using DMF
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2,4,6-Triguanidino-1,3,5-triazine and 2,4,6-tris(3-methylguanidino)-1,3,5-triazine were synthesized in 42 and 52percent yields, respectively, by the cyclotrimerization of cyanoguanidine and 1-methyl-3-cyanoguanidine using DMF as a solvent in the presence of hydrogen chloride. 1-Phenyl-3-cyanoguanidine, 1,2-dimethyl-3-cyanoguanidine, and 2-imidazolidinylidenecyanamide, however, were cyclodimerized to the corresponding guanidino-1,3,5-triazines in a similar manner.
- Iio, Kokoro,Ichikawa, Eiichi
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p. 2735 - 2736
(2007/10/02)
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- Bicyclic amidines
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New amidine/isocyanate adducts are particularly useful as catalysts for hardening epoxy resins, in particular pulverulent coating compositions based on epoxy resins. New bicyclic amidines are excellent starting materials for manufacturing these amidine/isocyanate adducts.
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- Reactions of Monosubstituted Guanidines with 1-Phenyl-1-butane-1,3-dione
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Methyl-, benzyl- and phenylguanidine (2b-d) react with 1-phenyl-1,3-butanedione to yield exclusively N2-substituted 4-methyl-6-phenyl-2-pyrimidinamines 10b-d.The formation of isomeric N1-substituted 2(1H)-pyrimidinimines 11 or 12 cannot be observed.The structural formulae of 10b and c were proved by spectroscopical methods.The structure of the phenylguanidine-phenylbutanedione-condensate was determined by comparison and establishment of the identity of its picrate with an authentical sample of 10d-picrate, which had been synthetized from pyrimidinthione 13 (via methylthiopyrimidine 16*HCl).Boiling 13 with aniline in butanol yields thiodipyrimidine 15 (and not 10d). - (Keywords: 1,3-Butanedione, 1-phenyl, reactions with monosubstituted guanidines; β-Diketones, reactions with monosubstituted guanidines; Guanidines, monosubstituted, reactions with 1-phenyl-1,3-butanedione; Pyridmidine, 4-methyl-2-methylthio-6-phenyl, hydroiodide; 2-Pyrimidine-amines, 4-methyl-6-phenyl-N2-substituted, and salts; 2,2'-Thiodipyrimidine, 4,4'-dimethyl-6,6'-diphenyl)
- Wendelin, Winfried,Schermanz,Karl,Schweiger, Klaus,Fuchsgruber, Alfred
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p. 1371 - 1380
(2007/10/02)
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