- Access to α,α-dihaloacetophenones through anodic C[dbnd]C bond cleavage in enaminones
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We have developed a method to synthesize α,α-dihaloketones under electrochemical conditions. In this reaction, the Cl- or Br- is oxidized to Cl2 or Br2 at the anode, which undergoes two-step addition reactions with the N,N-dimethyl enaminone, and finally breaks C[dbnd]C of the N,N-dimethyl enaminone to generate α,α-dihaloketones. The electrosynthesis reaction can be conveniently carried out in an undivided electrolytic cell at room temperature. In addition, various functional groups are compatible with this green protocol which can be applied simultaneously to the gram scale without significantly lower yield.
- Zhang, Zhenlei,Yang, Jiusi,Wu, Kairui,Yu, Renjie,Bu, Jiping,Huang, Zijun,Li, Shaoke,Ma, Xiantao
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supporting information
(2021/12/20)
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- Design, synthesis, in silico, and in vitro evaluation of 3-phenylpyrazole acetamide derivatives as antimycobacterial agents
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Mycobacterium tuberculosis (Mtb) is one of the most dangerous pathogens affecting immunocompetent and immunocompromised patients worldwide. Novel molecules, which are efficient and can reduce the duration of therapy against drug-resistant strains, are an
- Gaikwad, Nikhil B.,Nirmale, Krishna,Sahoo, Santosh K.,Ahmad, Mohammad N.,Kaul, Grace,Shukla, Manjulika,Nanduri, Srinivas,Das Gupta, Arunava,Chopra, Sidharth,Yaddanapudi, Madhavi V.
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- Sulfonamide-based ring-fused analogues for CAN508 as novel carbonic anhydrase inhibitors endowed with antitumor activity: Design, synthesis, and in vitro biological evaluation
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In the present study, we report the design and synthesis of novel CAN508 sulfonamide-based analogues (4, 8a-e, 9a-h and 10a-e) as novel carbonic anhydrase (CA) inhibitors with potential CDK inhibitory activity. A bioisosteric replacement approach was adop
- Said, Mohamed A.,Eldehna, Wagdy M.,Nocentini, Alessio,Fahim, Samar H.,Bonardi, Alessandro,Elgazar, Abdullah A.,Kry?tof, Vladimír,Soliman, Dalia H.,Abdel-Aziz, Hatem A.,Gratteri, Paola,Abou-Seri, Sahar M.,Supuran, Claudiu T.
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- Synthesis and in-vitro anti-proliferative evaluation of some pyrazolo[1,5-a]pyrimidines as novel larotrectinib analogs
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A series of 2-phenyl-7-(aryl)pyrazolo[1,5-a]pyrimidine-3-carbonitriles 11a–j and 2-phenyl-7-(aryl)pyrazolo[1,5-a]pyrimidine-3,6-dicarbonitriles 16a–c was synthesized by the reaction of 5-amino-3-phenyl-1H-pyrazole-4-carbonitrile (5) with 3-(dimethylamino)
- Attia, Mohamed H.,Elrazaz, Eman Z.,El-Emam, Soad Z.,Taher, Azza T.,Abdel-Aziz, Hatem A.,Abouzid, Khaled A.M.
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- Synthesis, characterization, antimicrobial activity, 3D-QSAR, DFT, and molecular docking of some ciprofloxacin derivatives and their copper(II) complexes
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Six new derivatives of ciprofloxacin compounds and their copper(II) complexes were synthesized, characterized by spectroscopic methods (ultraviolet–visible [UV–vis], Fourier transform infrared [FTIR], nuclear magnetic resonance [NMR], mass spectrometry [M
- Khalil, Tarek E.,El-Dissouky, Ali,Al-Wahaib, Dhuha,Abrar, Nada M.,El-Sayed, Doaa S.
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- SLC-0111 enaminone analogs, 3/4-(3-aryl-3-oxopropenyl) aminobenzenesulfonamides, as novel selective subnanomolar inhibitors of the tumor-associated carbonic anhydrase isoform IX
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SLC-0111, an ureido substituted benzenesulfonamide, is a selective carbonic anhydrase (CA, EC 4.2.1.1) IX inhibitor that is currently in Phase I/II clinical trials for the treatment of advanced hypoxic tumors complicated with metastases. Herein we report
- Eldehna, Wagdy M.,Abo-Ashour, Mahmoud F.,Berrino, Emanuela,Vullo, Daniela,Ghabbour, Hazem A.,Al-Rashood, Sara T.,Hassan, Ghada S.,Alkahtani, Hamad M.,Almehizia, Abdulrahman A.,Alharbi, Amal,Abdel-Aziz, Hatem A.,Supuran, Claudiu T.
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p. 549 - 558
(2018/11/26)
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- A catalyst-free four-component domino reaction for the synthesis of functionalized 3-acyl-1,5-benzodiazepines
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Various functional 3-acyl-1,5-benzodiazepines containing carboxyl, ester and acyl groups at the 2-position were synthesized via an efficient, sustainable and catalyst-free domino reaction. During the synthesis process, one new cycle and four new bonds (on
- Sun, Yue-Wei,Bei, Yue-Ming,Wang, Lan-Zhi
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p. 930 - 938
(2019/01/30)
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- The use of enaminones and enamines as effective synthons for MSA-catalyzed regioselective synthesis of 1,3,4-tri- And 1,3,4,5-tetrasubstituted pyrazoles
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In the present work, an efficient regioselective synthesis of 1,3,4-tri- and 1,3,4,5-tetrasubstituted pyrazoles via a methanesulfonic acid (MSA)-catalyzed reaction of hydrazones with enaminones or enamines is reported. Mechanistically, the formation of the title compounds involves the [2+3] cycloaddition of hydrazones with enaminones or enamines followed by aromatization with acid and oxygen. This convenient method under mild conditions with various hydrazones, enaminones, and enamines was well-tolerated to afford products in good to excellent yields. Compared with the literature methods, this strategy has advantages such as materials that are available economically, metal-free catalysis, excellent regioselectivity, and high efficiency.
- Duan, Liancheng,Zhou, Hui,Gu, Yucheng,Gong, Ping,Qin, Mingze
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supporting information
p. 16131 - 16137
(2019/11/03)
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- Phenylalaninamide pesticides and a preparing method thereof
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The invention relates to the technical fields of organic synthesis and application techniques, and particularly relates to phenylalaninamide pesticides and a preparing method thereof. Phenylalanine, substituted phenylacetic acid, and the like are adopted
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Paragraph 0025
(2018/04/02)
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- Cross-Dehydrogenative Coupling of Heterocyclic Scaffolds with Unfunctionalized Aroyl Surrogates by Palladium(II) Catalyzed C(sp2)-H Aroylation through Organocatalytic Dioxygen Activation
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Cross-dehydrogenative coupling of biorelevant heterocyclic scaffolds with arylmethanes for aroylation during Pd(II)-catalyzed C(sp2)-H activation has been achieved through dioxygen activation by NHPI. Mass spectrometry and 1H NMR based kinetic isotope effect studies revealed C-H bond activation as the rate-determining step. Radical scavenging experiments indicated a radical pathway. The 1H NMR of an aliquot of reaction mixture and in situ trapping with 2-aminothiophenol revealed the formation of aldehyde during aerobic oxidation of the arylmethanes. The reaction has broad scope for different variations of the aroyl source and the directing group that includes benzothiazole, benzooxazole, pyridine, quinoxaline, pyrimidine, and azoarene. The benzylic methylene moiety was found to be the source of the aroyl carbon with the benzyl ether moiety being the most preferred followed by the carbonyl group of aryl aldehyde and the aryl methane. However, the ease of availability of aryl methanes makes them the most attractive as an aroyl source. A time dependent selective mono- and bis-aroylation can be achieved. The 1,3-diarylpyrimidines exhibited regioselective aroylation of the 2-phenyl moiety irrespective of the absence or presence of any substitutent (electron withdrawing or electron donating) in the 3-phenyl moiety. For unsymmetrical azoarenes, selective aroylation took place in the phenyl moiety bearing the substituent.
- Pipaliya, Bhavin V.,Chakraborti, Asit K.
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p. 3767 - 3780
(2017/04/11)
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- Design, synthesis, and preliminary bioactivity evaluation of N-benzylpyrimidin-2-amine derivatives as novel histone deacetylase inhibitor
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Histone deacetylase (HDAC) inhibitors have been identified for the treatment of cancer. Lately, we designed and synthesized a series of substituted N-benzylpyrimidin-2-amine derivatives as potent HDAC inhibitors. In vitro HDAC inhibitory activities and an
- Zhou, Yi,Dun, Yanyan,Fu, Huansheng,Wang, Lei,Pan, Xiaole,Yang, Xinying,Fang, Hao
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p. 936 - 942
(2017/10/05)
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- Enaminones as building blocks: Synthesis of novel substituted pyrazoles as possible antioxidants
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An efficient synthesis of some new novel series of 1,5-disubstituted pyrazole derivatives have been achieved by reacting different enaminones with various hydrazines. The structures of the newly synthesized compounds have been elucidated from elemental an
- Shetty, Shobhitha,Asma,Kalluraya, Balakrishna
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p. 501 - 506
(2017/01/18)
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- Synthesis, and docking studies of phenylpyrimidine-carboxamide derivatives bearing 1H-pyrrolo[2,3-b]pyridine moiety as c-Met inhibitors
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Four series of phenylpyrimidine-carboxamide derivatives bearing 1H-pyrrolo[2,3-b]pyridine moiety (14a-e, 15a-g, 16a-e and 17a-g) were designed, synthesized and evaluated for the IC50 values against three cancer cell lines (A549, PC-3 and MCF-7). Four selected compounds (15e, 16a-b and 17a) were further evaluated for the activity against c-Met kinase, HepG2 and Hela cell lines. Most of the compounds showed excellent cytotoxicity activity and selectivity with the IC50 valuables in single-digit μM to nanomole range. Eleven of them are equal to more active than positive control Foretinib against one or more cell lines. The most promising compound 15e showed superior activity to Foretinib against A549, PC-3 and MCF-7 cell lines, with the IC50 values of 0.14 ± 0.08 μM, 0.24 ± 0.07 μM and 0.02 ± 0.01 μM, which were 4.6, 1.6 and 473.5 times more active than Foretinib (0.64 ± 0.26 μM, 0.39 ± 0.11 μM, 9.47 ± 0.22 μM), respectively. Structure-activity relationships (SARs) and docking studies indicated that the replacement of phenylpicolinamide scaffold with phenylpyrimidine fragment of the target compounds was benefit for the activity. What's more, the introduction of fluoro atom to the aminophenoxy part played no significant impact on the activity and any substituent group on aryl group is unfavourable for the activity.
- Zhu, Wufu,Wang, Wenhui,Xu, Shan,Wang, Jianqiang,Tang, Qidong,Wu, Chunjiang,Zhao, Yanfang,Zheng, Pengwu
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p. 1749 - 1756
(2016/04/05)
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- Synthesis, activity and docking studies of phenylpyrimidine–carboxamide Sorafenib derivatives
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Two series of Sorafenib derivatives bearing phenylpyrimidine–carboxamide moiety (16a–g and 17a–p) were designed, synthesized and evaluated for the IC50values against three cancer cell lines (A549, MCF-7 and PC-3). Two selected compounds (17f and 17n) were further evaluated for the activity against VEGFR2/KDR kinase. More than half of the synthesized compounds showed moderate to excellent activity against three cancer cell lines. Compound 17f showed equal activity to Sorafenib against MCF-7 cell line, with the IC50values of 6.35 ± 0.43 μM. Meanwhile, compound 17n revealed more active than Sorafenib against A549 cell line, with the IC50values of 3.39 ± 0.37 μM. Structure–activity relationships (SARs) and docking studies indicated that the second series (17a–p) showed more active than the first series (16a–g). What's more, the introduction of fluoro atom to the phenoxy part played no significant impact on activity. In addition, the presence of electron-donating on aryl group was benefit for the activity.
- Wang, Wenhui,Wu, Chunjiang,Wang, Jianqiang,Luo, Rong,Wang, Caolin,Liu, Xiaobo,Li, Jiqing,Zhu, Wufu,Zheng, Pengwu
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p. 6166 - 6173
(2016/12/06)
-
- HEPARAN SULFATE BIOSYNTHESIS INHIBITORS FOR THE TREATMENT OF DISEASES
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Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions in need of inhibition of heparan sulfate biosynthesis.
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-
Paragraph 000352
(2016/05/02)
-
- Synthesis and Cation Recognition Study of Novel Benzo Crown Ether Functionalized Enamine Derivatives
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A novel series of benzo crown ether (dibenzo 18-crown-6 ether, benzo 18-crown-6 ether, and benzo 15-crown-5 ether) functionalized enamines derivatives from amino benzo crown ether (4-amino dibenzo 18-crown-6 ether, 4-amino benzo 18-crown-6 ether, 4-amino
- Patil, Dayanand R.,Chandam, Dattatraya R.,Mulik, Abhijeet G.,Jagdale, Suryabala D.,Patil, Prasad P.,Deshmukh, Madhukar B.
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supporting information
p. 1902 - 1911
(2015/08/03)
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- DMF Dimethyl Acetal as Carbon Source for α-Methylation of Ketones: A Hydrogenation-Hydrogenolysis Strategy of Enaminones
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A novel heterogeneous catalytic hydrogenation-hydrogenolysis strategy has been developed for the α-methylation of ketones via enaminones using DMF dimethyl acetal as carbon source. This strategy provides a very convenient route to α-methylated ketones using a variety of ketones without any base or oxidant. (Chemical Equation Presented).
- Borah, Ashwini,Goswami, Limi,Neog, Kashmiri,Gogoi, Pranjal
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p. 4722 - 4728
(2015/05/13)
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- Novel synthesis of 6-substituted 2-picolines from aryl/heteroaryl β-enaminones and meldrum's acid using cecl3.7H2o/nai
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One-pot condensation of aryl/heteroaryl β-enaminones, Meldrum's acid, and ammonium acetate in the presence of CeCl3.7H2O/NaI via tandem Michael addition-cyclodehydration-elimination sequence led to the formation of novel regioselecti
- Addla, Dinesh,Kantevari, Srinivas
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p. E384-E388
(2014/11/08)
-
- Regioselective copper(I)-catalyzed C-H hydroxylation/C-S coupling: Expedient construction of 2-(styrylthio)phenols
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Regioselective copper(I)-catalyzed C-H hydroxylation/C-S coupling of aryl thiols with vinyl halides was developed. Starting from substituted aryl thiols and vinyl halides, various 2-(styrylthio)phenol derivatives were efficiently prepared. The application of the synthetic methodology to generate the bioactive organic intermediate was also exemplified.
- Xu, Run-Sheng,Yue, Lei,Pan, Yuan-Jiang
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experimental part
p. 5046 - 5052
(2012/08/07)
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- Facile diversity-oriented synthesis and antitubercular evaluation of novel aryl and heteroaryl tethered pyridines and dihydro-6H-quinolin-5-ones derived via variants of the Bohlmann-Rahtz reaction
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The diversity oriented synthesis of substituted pyridines and dihydro-6H-quinolin-5-ones tethered with aryls and heteroaryls was achieved in very good yields through CeCl3?7H2O-NaI catalyst via variants of the Bohlmann-Rahtz reaction
- Kantevari, Srinivas,Patpi, Santhosh Reddy,Addla, Dinesh,Putapatri, Siddamal Reddy,Sridhar, Balasubramanian,Yogeeswari, Perumal,Sriram, Dharmarajan
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experimental part
p. 427 - 435
(2011/09/14)
-
- Discovery of GSK1070916, a potent and selective inhibitor of aurora B/C kinase
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The Aurora kinases play critical roles in the regulation of mitosis and are frequently overexpressed or amplified in human tumors. Selective inhibitors may provide a new therapy for the treatment of tumors with Aurora kinase amplification. Herein we describe our lead optimization efforts within a 7-azaindole-based series culminating in the identification of GSK1070916 (17k). Key to the advancement of the series was the introduction of a 2-aryl group containing a basic amine onto the azaindole leading to significantly improved cellular activity. Compound 17k is a potent and selective ATP-competitive inhibitor of Aurora B and C with Ki* values of 0.38 ± 0.29 and 1.5 ± 0.4 nM, respectively, and is >250-fold selective over Aurora A. Biochemical characterization revealed that compound 17k has an extremely slow dissociation half-life from Aurora B (>480 min), distinguishing it from clinical compounds 1 and 2. In vitro treatment of A549 human lung cancer cells with compound 17k results in a potent antiproliferative effect (EC50 = 7 nM). Intraperitoneal administration of 17k in mice bearing human tumor xenografts leads to inhibition of histone H3 phosphorylation at serine 10 in human colon cancer (Colo205) and tumor regression in human leukemia (HL-60). Compound 17k is being progressed to human clinical trials.
- Adams, Nicholas D.,Adams, Jerry L.,Burgess, Joelle L.,Chaudhari, Amita M.,Copeland, Robert A.,Donatelli, Carla A.,Drewry, David H.,Fisher, Kelly E.,Hamajima, Toshihiro,Hardwicke, Mary Ann,Huffman, William F.,Koretke-Brown, Kristin K.,Lai, Zhihong V.,McDonald, Octerloney B.,Nakamura, Hiroko,Newlander, Ken A.,Oleykowski, Catherine A.,Parrish, Cynthia A.,Patrick, Denis R.,Plant, Ramona,Sarpong, Martha A.,Sasaki, Kosuke,Schmidt, Stanley J.,Silva, Domingos J.,Sutton, David,Tang, Jun,Thompson, Christine S.,Tummino, Peter J.,Wang, Jamin C.,Xiang, Hong,Yang, Jingsong,Dhanak, Dashyant
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experimental part
p. 3973 - 4001
(2010/08/07)
-
- One-pot synthesis of enaminones using gold's reagent
-
Enaminones were efficiently prepared via modification for Gupton method, which depends on carrying out the latter procedure in one step reaction, avoiding the isolation of [3-(dimethylamino)-2-azaprop-2-en-1-ylidene] dimethylammonium chloride (Gold's reag
- Saleh, Tamer S.,Al-Omar, Mohamed A.,Abdel-Aziz, Hatem A.
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experimental part
p. 483 - 486
(2011/09/16)
-
- Synthesis and structure-activity relationship of aminopyrimidine IKK2 inhibitors
-
The synthesis and structure-activity relationship of a novel series of aminopyrimidines are exemplified. Results of key compounds from within this series in the E-selectin reporter cell assay are also reported.
- Bingham, Alistair H.,Davenport, Richard J.,Fosbeary, Richard,Gowers, Lewis,Knight, Roland L.,Lowe, Christopher,Owen, David A.,Parry, David M.,Pitt, Will R.
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scheme or table
p. 3622 - 3627
(2009/04/06)
-
- SUBSTITUTED 2-AMINO- 1,2,4 TRIAZOLO 1,5-a PYRIMIDINE DERIVATIVE AND USE THEREOF
-
Disclosed is a [1,2,4]triazolo[1,5-a]pyrimidine derivative represented by the general formula (I) below or a pharmaceutically acceptable salt thereof. Also disclosed is a medicine containing such a derivative or a salt thereof as an active constituent. In
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-
Page/Page column 19
(2008/06/13)
-
- Phenylazole compounds, process for producing the same and drugs for hyperlipemia
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Phenylazole compounds represented by general formula (1) or pharmaceutically acceptable salts thereof and drugs for hyperlipemia which contain these compounds as the active ingredient, wherein A represents imidazolyl, pyrazolyl, etc.; B represents (1a) or (1b) (wherein R2and R3represent each hydrogen, C1-6alkyl, etc; and k is 0 or an integer of 1 to 15); Y represents O, S, a bond, etc.; and Z represents an optionally substituted and saturated or unsaturated heterocycle containing 1 to 4 N, O or S atoms. Among all, compounds wherein Z is substituted chroman-2-yl, 2,3-dihydrobenzofuran-2-yl, etc. have an effect of inhibiting the formation of lipid peroxides too.
- -
-
Referential example 1
(2008/06/13)
-
- SUBSTITUTED HETEROCYCLYL-PHENYLFORMAMIDINES AND SALTS THEREOF
-
Compounds of the formula STR1 wherein R is hydrogen or methyl;R 1 is straight or branched alkyl of 1 to 6 carbon atoms, hydroxy(alkyl of 1 to 6 carbon atoms), mono-or di-(alkoxy of 1 to 6 carbon atoms)(alkyl of 1 to 6 carbon atoms), (alkyl of 1 to 6 cabon atoms) thio(alkyl of 1 to 6 carbon atoms), cyano(alkyl of 1 to 6 carbon atoms), alkenyl, alkynyl, or cycloalkyl;R 2 is hydrogen, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms or halogen; andX is pyrazol-3-yl, 1,2,4-triazol-3-yl, pyridin-2-yl, pyridin-3-yl, thiazol-4-yl, 2-methyl-thiazol-4-yl or 2-methylamino-thiazol-4-yl;tautomers thereof, and non-toxic, pharmacologiically acceptable acid addition salts thereof. The compounds as well as their salts are useful as antiulcerogenics and gastric acid secretion inhibitors.
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