- Specific 1,2-Hydride Shift in the Boron Trifluoride Catalyzed Reactions of Aromatic Aldehydes with Diazoacetonitrile: Simple Synthesis of β-Ketonitriles
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A series of β-ketonitriles was synthesized within 30 min under mild conditions through the BF3 ·OEt2-catalyzed addition reactions of diazoacetonitrile to aromatic aldehydes and subsequent 1,2-hydride shift. This method is advantageous in that it is operationally simple, mild and metal-free conditions are used, the substrate scope is wide, and the products are obtained in moderate to high yields (up to 81 %). Additionally, γ,δ-unsaturated β-ketonitriles are also accessible by this method by using cinnamaldehydes.
- Yang, Zhanhui,Son, Kwon-Il,Li, Siqi,Zhou, Bingnan,Xu, Jiaxi
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Read Online
- Asymmetric Hydroacylation Involving Alkene Isomerization for the Construction of C3-Chirogenic Center
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A new transformation pattern for enantioselective intramolecular hydroacylation has been developed involving an alkene isomerization strategy. Proceeding through a five-membered rhodacycle intermediate, 3-enals were converted to C3- or C3,C5-chirogenic cyclopentanones with satisfactory yields, diastereoselectivities, and enantioselectivities. A catalytic cycle has been theoretically calculated and the origin of the stereoselection is rationally explained.
- Liu, Chong,Yuan, Jing,Zhang, Zhenfeng,Gridnev, Ilya D.,Zhang, Wanbin
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supporting information
p. 8997 - 9002
(2021/03/16)
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- Deadly KCN and pricey metal free track for accessing β-ketonitriles employing mild reaction conditions
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A one pot synthesis of β-ketonitriles from readily accessible 3-chloropropenals using economically benign iodine, aqueous ammonia and sodium hydroxide solution, employing mild reaction conditions have been described. This report presents a convenient, inexpensive, highly toxic-matter-free and eco-friendly approach for β-ketonitriles.
- Sharma, Pawan K.,Kumar, Rajiv,Ram, Sita,Chandak, Navneet
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supporting information
p. 1847 - 1856
(2021/04/26)
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- Selective Synthesis of β-Ketonitriles via Catalytic Carbopalladation of Dinitriles
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A practical, convenient, and highly selective method of synthesizing β-ketonitriles from the Pd-catalyzed addition of organoboron reagents to dinitriles has been developed. This method provides excellent functional-group tolerance, a broad scope of substrates, and the convenience of using commercially available substrates. The method is expected to show further utility in future synthetic procedures.
- Zeng, Ge,Liu, Jichao,Shao, Yinlin,Zhang, Fangjun,Chen, Zhongyan,Lv, Ningning,Chen, Jiuxi,Li, Renhao
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p. 861 - 867
(2021/01/09)
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- COMPOUNDS AND METHODS FOR TREATING CANCER
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Compounds useful as modulators of AhR, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or ameliorate AhR-mediated disorders such as cancers and inflammatory diseases are provided.
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Paragraph 0227
(2020/11/30)
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- One-pot dichlorinative deamidation of primary β-ketoamides
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An approach to the dichlorinative deamidation of primary β-ketoamides through ketonic cleavage is described, and a series of α,α-dichloroketones were furnished mostly in the presence of TEMPO. Based on control experiments, a mechanism involving tandem dichlorination and deamidation is proposed to interpret the observed reactivity.
- Zheng, Congke,Zhang, Xiaohui,Ijaz Hussain, Muhammad,Huang, Mingming,Liu, Qing,Xiong, Yan,Zhu, Xiangming
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supporting information
p. 574 - 577
(2017/01/16)
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- SeO2-Mediated One-Pot Synthesis of 3-Cyanofurans from 3-Oxo-3-arylpropanenitriles and Substituted Acetaldehydes
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An SeO2-mediated one-pot method was established for the synthesis of 3-cyanofurans from 3-oxo-3-arylpropanenitriles and substituted acetaldehydes. The generality of the reaction was explored, and a plausible mechanism is proposed.
- Zhou, Jie,Zhu, Xinhai,Huang, Manna,Wan, Yiqian
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supporting information
p. 2317 - 2321
(2017/05/01)
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- HETEROCYCLE SUBSTITUTED AMINO-PYRIDINE COMPOUNDS AND METHODS OF USE THEREOF
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The present disclosure relates to heterocycle substituted amino-pyridine compounds. The present disclosure also relates to pharmaceutical compositions containing these compounds and methods of treating cancer by administering these compounds and pharmaceutical compositions to subjects in need thereof. The present disclosure also relates to the use of such compounds for research or other non-therapeutic purposes.
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Paragraph 0485; 0486
(2016/04/20)
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- Umpolung Strategy for Synthesis of β-Ketonitriles through Hypervalent Iodine-Promoted Cyanation of Silyl Enol Ethers
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An efficient method to synthesize β-ketonitriles from silyl enol ethers by an umploung hypervalent iodine(III)-CN species generated in situ from PhIO/BF3·Et2O/TMSCN has been developed for the first time. This method can be applied to structurally diverse aromatic and aliphatic substrates and further extended to preparation of bioactive compounds like 5-aminopyrazole and 5-aminoisoxazole.
- Shen, Hang,Li, Jiaqiang,Liu, Qing,Pan, Jing,Huang, Ruofeng,Xiong, Yan
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p. 7212 - 7218
(2015/07/28)
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- WNT PATHWAY MODULATORS
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The present invention relates to dihydropyrazolo[l,5-a]pyrimidine compounds of formula I, defined herein, as WNT pathways modulators, processes for making them, and pharmaceutical compositions comprising them. Methods of treatment of conditions mediated by WNT pathway signalling including cancer, fibrosis, stem cell and diabetic retinopathy, rheumatoid arthritis, psoriasis and myocardial infarction, comprising the compounds of formula I are also provided.
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Paragraph 0195; 0196; 0234; 0235
(2015/07/07)
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- Copper-catalyzed Aerobic Oxidative coupling of Aromatic Alcohols and Acetonitrile to β-Ketonitriles
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A practical, convenient, and cheap coppercatalyzed aerobic oxidative coupling of aromatic alcohols and acetonitrile to β-ketonitriles has been developed. The green C-C bond formation involving the loss of two hydrogen atoms from the corresponding two carbons, respectively, unlocks opportunities for markedly different synthetic strategies.
- Shen, Jiaxuan,Yang, Dejun,Liu, Yuxiao,Qin, Shuangshuang,Zhang, Jingwu,Sun, Jiangkai,Liu, Chunhui,Liu, Chaoyang,Zhao, Xiaomei,Chu, Changhu,Liu, Renhua
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supporting information
p. 350 - 353
(2014/04/03)
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- Cascade synthesis of 3-aza-bicyclo[3.1.0]hex-2-ene derivatives from N-allyl enamines
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An efficient iodine-mediated cascade synthesis of 3-aza-bicyclo[3.1.0]hex-2-ene derivatives from easily prepared N-allyl enamines has been developed. The advantages of the reaction include facilitative preparation of substrates 3a-t, good functional group tolerance and transition-metal-free conditions.
- Zhai, Sheng-Xian,Dong, Hong-Ru,Chen, Zi-Bao,Hu, Yi-Ming,Dong, Heng-Shan
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p. 8405 - 8412
(2015/03/04)
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- Synthesis and biological evaluation of triazolothienopyrimidine derivatives as novel HIV-1 replication inhibitors
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We identified a novel class of triazolothienopyrimidine (TTPM) compounds as potent HIV-1 replication inhibitors during a high-throughput screening campaign that evaluated more than 200,000 compounds using a cell-based full replication assay. Herein, we report the optimization of the antiviral activity in a cell-based assay system leading to the discovery of aryl-substituted TTPM derivatives (38, 44, and 45), which exhibited significant inhibition of HIV-1 replication with acceptable safety margins. These novel and potent TTPMs could serve as leads for further development.
- Kim, Junwon,Kwon, Jeongjin,Lee, Doohyun,Jo, Suyeon,Park, Dong-Sik,Choi, Jihyun,Park, Eunjung,Hwang, Jong Yeon,Ko, Yoonae,Choi, Inhee,Ju, Moon Kyeong,Ahn, Jiye,Kim, Junghwan,Han, Sung-Jun,Kim, Tae-Hee,Cechetto, Jonathan,Nam, Jiyoun,Ahn, Sujin,Sommer, Peter,Liuzzi, Michel,No, Zaesung,Lee, Jinhwa
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p. 153 - 157
(2013/02/23)
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- Palladium-catalyzed carbonylation with Mo(CO)for the synthesis of benzoylacetonitriles
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Benzoylacetonitriles were synthesized by the palladium-catalyzed carbonylation of aryl iodides and trimethylsilylacetonitrile using Mo(CO)as a carbon monoxide source. Pd(PPhCland CuFwere employed as the catalyst and activator, respectively. A variety of aryl iodides bearing alkyl, alkoxy, fluoro, chloro, bromo, nitrile, ester, and ketone groups afforded the corresponding benzoylacetonitriles in moderate to good yields. Georg Thieme Verlag Stuttgart ? New York.
- Pyo, Ayoung,Park, Ahbyeol,Jung, Hyunmin,Lee, Sunwoo
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supporting information
p. 2885 - 2888
(2012/10/29)
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- Synthesis and biological evaluation of 3-aryl-quinoxaline-2- carbonitrile 1,4-Di-N-oxide derivatives as hypoxic selective anti-tumor agents
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A series of 3-aryl-2-quinoxaline-carbonitrile 1,4-di-N-oxide derivatives were designed, synthesized and evaluated for hypoxic and normoxic cytotoxic activity against human SMMC-7721, K562, KB, A549 and PC-3 cell lines. Many of these new compounds displayed more potent hypoxic cytotoxic activity compared with TX-402 and TPZ in the tumor cells based evaluation, which confirmed our hypothesis that the replacement of the 3-amine with the substituted aryl ring of TX-402 increases the hypoxic anti-tumor activity. The preliminary SAR revealed that 3-chloro was a favorable substituent in the phenyl ring for hypoxic cytotoxicity and 7-methyl or 7-methoxy substituted derivatives exhibited better hypoxic selectivity against most of the tested cell lines. The most potent compound, 7-methyl-3-(3-chlorophenyl)-quinoxaline-2-carbonitrile 1,4-dioxide (9h) was selected for further anti-tumor evaluation and mechanistic study. It also exhibited significant cytotoxic activity against BEL-7402, HepG2, HL-60, NCI-H460, HCT-116 and CHP126 cell lines in hypoxia with IC50 values ranging from 0.31 to 3.16 μM, and preliminary mechanism study revealed that 9h induced apoptosis in a caspase-dependent pathway.
- Hu, Yunzhen,Xia, Qing,Shangguan, Shihao,Liu, Xiaowen,Hu, Yongzhou,Sheng, Rong
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p. 9683 - 9696
(2012/11/13)
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- Transfer hydrogenation in water: Enantioselective, catalytic reduction of α-cyano and α-nitro substituted acetophenones
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Catalytic reduction of α-substituted acetophenones under conditions involving asymmetric transfer hydrogenation in water is described. The reaction is conducted in water and open to air, and formic acid is used as reductant.
- Soltani, Omid,Ariger, Martin A.,Vazquez-Villa, Henar,Carreira, Erick M.
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supporting information; experimental part
p. 2893 - 2895
(2010/09/09)
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- Design, synthesis, and evaluation of 2-aryl-7-(3′,4′-dialkoxyphenyl)-pyrazolo[1,5-a]pyrimidines as novel PDE-4 inhibitors
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Described herein is design, synthesis, and biological evaluation of novel series of 2-aryl-7-(3′,4′-dialkoxyphenyl)-pyrazolo[1,5-a]pyrimidines acting as inhibitors of type 4 phosphodiesterase (PDE4) which is known as a good target for the treatment of asthma and COPD. For this purpose, structure optimization was conducted with the aid of structure-based drug design using the known X-ray crystallography. Also, biological effects of these compounds on the target enzyme were evaluated by using in vitro assays, leading to the potent and selective PDE-4 inhibitor (IC50 10 nM).
- Kim, Ikyon,Song, Jong Hwan,Park, Chang Min,Jeong, Joon Won,Kim, Hyung Rae,Ha, Jin Ryul,No, Zaesung,Hyun, Young-Lan,Cho, Young Sik,Sook Kang, Nam,Jeon, Dong Ju
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scheme or table
p. 922 - 926
(2010/06/22)
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- De novo parallel design, synthesis and evaluation of inhibitors against the reverse transcriptase of human immunodeficiency virus type-1 and drug-resistant variants
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We used molecular modeling to design de novo broad-range inhibitors against wild type and drug-resistant variants of the reverse transcriptase (RT) of human immunodeficiency virus type-1 (HIV-1). First, we screened for small fragments that would interact with each one of four RT structures (one wild type and three mutants). Then, these fragments were linked to build a scaffold molecule. Out of 27 different compounds that were synthesized, four inhibited the DNA polymerase activity of RT with IC50 values below 10 μM. Compound 5f inhibited RT with an IC50 value of about 3.5 μM, while inhibiting drug-resistant RT variants more efficiently than the clinically used drug, nevirapine (11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b: 2′,3′-e-]-[1,4]diazepin-6-one). 5f also inhibited the RT ribonuclease H activity with an IC50 of 20 μM and therefore, unlike nevirapine, targets both RT activities. Accordingly, 5f can serve as lead for developing novel inhibitors against RT that may be used to suppress HIV-1 growth.
- Herschhorn, Alon,Lerman, Lena,Weitman, Michal,Gleenberg, Iris Oz,Nudelman, Abraham,Hizi, Amnon
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p. 2370 - 2384
(2008/02/07)
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- 3-Substituted-(5-arylfuran-2-ylcarbonyl)guanidines as NHE-1 inhibitors
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The C-3 substituents effect on NHE-1 inhibitory activity of (5-arylfuran-2-ylcarbonyl)guanidines, previously identified as potent NHE-1 inhibitors, was investigated. The introduction of amine or alkyl groups at the 3-position of the furan ring, next to the acylguanidine moiety, remarkably improves NHE-1 inhibitory potency. Especially the important finding is that 5-(2,5-dichloro)phenyl and 5-(2-methoxy-5-chloro)phenyl derivatives exhibit high NHE-1 inhibitory activities (IC50 0.02 μM) that match those of 3-unsubstituted derivatives.
- Lee, Sunkyung,Kim, Taemi,Lee, Byung Ho,Yoo, Sung-eun,Lee, Kyunghee,Yi, Kyu Yang
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p. 1291 - 1295
(2008/02/02)
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- Novel potent neuropeptide Y Y5 receptor antagonists: Synthesis and structure-activity relationships of phenylpiperazine derivatives
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A series of phenylpiperazine derivatives were synthesized and evaluated for their neuropeptide Y (NPY) Y5 receptor antagonistic activities. The benzindane portion of 2 was replaced by 1-phenylpiperazine, resulting in novel urea derivative 3f. Subsequent optimization of the phenylpiperazine template by substitution of the phenyl moiety resulted in a series of (2-methanesulfonamidephenyl)piperazine derivatives that showed potent binding affinity and antagonistic activity for the Y5 receptor.
- Takahashi, Toshiyuki,Sakuraba, Aya,Hirohashi, Tomoko,Shibata, Takunobu,Hirose, Masaaki,Haga, Yuji,Nonoshita, Katsumasa,Kanno, Tetsuya,Ito, Junko,Iwaasa, Hisashi,Kanatani, Akio,Fukami, Takehiro,Sato, Nagaaki
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p. 7501 - 7511
(2007/10/03)
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- NOVEL HERBICIDES, USAGE THEREOF, NOVEL THIENOPYRIMIDINE DERIVATIVES, INTERMEDIATES OF THE SAME, AND PROCESS FOR PRODUCTION THEREOF
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A herbicide comprising, as an active ingredient, a substituted thienopyrimidine derivative represented by the formula (I): wherein all symbols are defined in the description, a method of using the same, a novel compound useful as the herbicide and a process for producing the same, and an intermediate thereof.
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Page/Page column 57
(2010/02/12)
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- Pyrazolo[1,5-a]pyrido[3,4-e]pyrimidin-6-ones. II. Synthesis and in vitro antimicrobial evaluation
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A series of pyrazolo[1,5-a]pyrido[3,4-e]pyrimidin-6-ones (4a-p) was prepared by a simple synthetic procedure based on the reaction of hydroxylamine or methoxyamine with 2,3-substituted ethyl 7-dimethylaminovinyl pyrazolo[1,5-a]pyrimidin-6-carboxylates (3a
- Bruni,Selleri,Costanzo,Guerrini,Ciciani,Costagli,Sacco,Donato
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p. 639 - 643
(2007/10/03)
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- Heteroaryl 3-oxo-propanenitrile derivatives, pharmaceutical compositions and use
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The invention relates to compounds having the general formula (I) STR1 and the pharmaceutically acceptable salts thereof, which possess immunomodulating activity and are useful e.g. in the treatment of neoplastic diseases and acute and chronic infections of both bacterial and viral origin in mammals.
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