- Deadly KCN and pricey metal free track for accessing β-ketonitriles employing mild reaction conditions
-
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
-
supporting information
p. 1847 - 1856
(2021/04/26)
-
- Selective Synthesis of β-Ketonitriles via Catalytic Carbopalladation of Dinitriles
-
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
-
p. 861 - 867
(2021/01/09)
-
- One-Pot Four-Component Coupling Approach to Polyheterocycles: 6 H-Furo[3,2- f]pyrrolo[1,2- d][1,4]diazepine
-
A novel polyheterocyclic chemical space, 6H-furo[3,2-f]pyrrolo[1,2-d][1,4]diazepine, was generated by a one-pot four-component coupling reaction where multiple bonds (three C-C, one C-O, and one C-N) were formed through a domino sequence. Two heterocyclic rings (furan and diazepine) were sequentially constructed from the monocyclic pyrrole derivative under environment-friendly reaction conditions to furnish the tricyclic fused scaffold.
- Yoon, Seok Hyun,Kim, Sung June,Kim, Ikyon
-
p. 15082 - 15091
(2020/12/02)
-
- 3-PHOSPHOGLYCERATE DEHYDROGENASE INHIBITORS AND USES THEREOF
-
The present invention provides compounds, compositions thereof, and methods of using the same.
- -
-
-
- One-pot synthesis of benzoylacetonitriles through sequential Pd-catalyzed carbonylation and decarboxylation
-
Benzoylacetonitrile were prepared through sequential carbonylation and decarboxylation. The palladium-catalyzed carbonylation of aryl iodides and methyl cyanoacetate using Mo(CO)6 as a carbon monoxide source afforded beta-keto cyanoesters, and then the subsequent reaction with Li/H2O produced the desired benzoylacetonitriles.
- Lee, Sunwoo,Kim, Han-Sung,Min, Hongkeun,Pyo, Ayoung
-
p. 239 - 242
(2015/12/31)
-
- PYRAZOLOPYRIMIDINE MACROCYCLES AS INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION
-
The disclosure generally relates to compounds of formula I, including compositions and methods for treating human immunodeficiency virus (HIV) infection. The disclosure provides novel inhibitors of HIV, pharmaceutical compositions containing such compounds, and methods for using these compounds in the treatment of HIV infection.
- -
-
Page/Page column 18; 19
(2015/09/22)
-
- PYRAZOLOPYRIMIDINE MACROCYCLES AS INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION
-
The disclosure generally relates to compounds of formula I, including compositions and methods for treating human immunodeficiency virus (HIV) infection. The disclosure provides novel inhibitors of HIV integrase, pharmaceutical compositions containing such compounds, and methods for using these compounds in the treatment of HIV infection.
- -
-
Page/Page column 21
(2015/09/23)
-
- PYRAZOLOPYRIMIDINE MACROCYCLES AS INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION
-
The disclosure generally relates to compounds of formula I, including compositions and methods for treating human immunodeficiency virus (HIV) infection. The disclosure provides novel inhibitors of HIV, pharmaceutical compositions containing such compound
- -
-
Page/Page column 23; 24
(2015/09/28)
-
- Cascade synthesis of 3-aza-bicyclo[3.1.0]hex-2-ene derivatives from N-allyl enamines
-
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
-
p. 8405 - 8412
(2015/03/04)
-
- INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION
-
The disclosure generally relates to compounds of formula (I), including compositions and methods for treating human immunodeficiency virus (HIV) infection. The disclosure provides novel inhibitors of HIV, pharmaceutical compositions containing such compou
- -
-
Page/Page column 24; 25
(2014/03/22)
-
- Palladium-catalyzed carbonylation with Mo(CO)for the synthesis of benzoylacetonitriles
-
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
-
supporting information
p. 2885 - 2888
(2012/10/29)
-
- Design, synthesis, and evaluation of 2-aryl-7-(3′,4′-dialkoxyphenyl)-pyrazolo[1,5-a]pyrimidines as novel PDE-4 inhibitors
-
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
-
scheme or table
p. 922 - 926
(2010/06/22)
-
- Synthesis of pyrazolo[1,5-α]pyrimidinone regioisomers
-
(Chemical Equation Presented) This work describes two distinct routes to prepare pyrazolo-[1,5-α]pyrimidin-7-ones and two distinct routes to prepare pyrazolo[1,5-α]pyrimidin-5-ones. Use of 1,3-dimethyluracil as the electrophile in the preparation of the p
- Gavrin, Lori K.,Lee, Arthur,Provencher, Brian A.,Massefski, Walter W.,Huhn, Stephen D.,Ciszewski, Gregory M.,Cole, Derek C.,McKew, John C.
-
p. 1043 - 1046
(2008/02/04)
-
- Discovery of S-[5-amino-1-(4-fluorophenyl)-1H-pyrazol-4-yl]-[3-(2,3- dihydroxypropoxy)phenyl]-methanone (RO3201195), an orally bioavailable and highly selective inhibitor of p38 Map kinase
-
A novel class of highly selective inhibitors of p38 MAP kinase was discovered from high throughput screening. The synthesis and optimization of a series of 5-amino-N-phenyl-1H-pyrazol-4-yl-3-phenylmethanones is described. An X-ray crystal structure of this series bound in the ATP binding pocket of unphosphorylated p38a established the presence of a unique hydrogen bond between the exocyclic amine of the inhibitor and threonine 106 which likely contributes to the selectivity for p38. The crystallographic information was used to optimize the potency and physicochemical properties of the series. The incorporation of the 2,3-dihydroxypropoxy moiety on the pyrazole scaffold resulted in a compound with excellent drug-like properties including high oral bioavailability. These efforts identified 63 (RO3201195) as an orally bioavailable and highly selective inhibitor of p38 which was selected for advancement into Phase I clinical trials.
- Goldstein, David M.,Alfredson, Tom,Bertrand, Jay,Browner, Michelle F.,Clifford, Ken,Dalrymple, Stacie A.,Dunn, James,Freire-Moar, Jose,Harris, Seth,Labadie, Sharada S.,La Fargue, JoAnn,Lapierre, Jean Marc,Larrabee, Susan,Li, Fujun,Papp, Eva,McWeeney, Daniel,Ramesha, Chakk,Roberts, Rick,Rotstein, David,San Pablo, Bong,Sjogren, Eric B.,So, On-Yee,Talamas, Francisco X.,Tao, Will,Trejo, Alejandra,Villasenor, Armando,Welch, Mary,Welch, Teresa,Weller, Paul,Whiteley, Phyllis E.,Young, Kelly,Zipfel, Sheila
-
p. 1562 - 1575
(2007/10/03)
-
- NOVEL HERBICIDES, USAGE THEREOF, NOVEL THIENOPYRIMIDINE DERIVATIVES, INTERMEDIATES OF THE SAME, AND PROCESS FOR PRODUCTION THEREOF
-
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.
- -
-
Page/Page column 57
(2010/02/12)
-
- Synthetic studies on selective type 4 phosphodiesterase (PDE 4) inhibitors. 1. Structure-activity relationships and pharmacological evaluation of 1,8-naphthyridin-2(1H)-one derivatives.
-
In order to develop novel and orally active phosphodiesterase (PDE) 4 inhibitors, random screening was performed using our chemical library to find YM-10335 possessing the 1,8-naphthyridin-2(1H)-one skeleton which is a completely different structure from rolipram. In this report, the syntheses and structure-activity relationships of the YM-10335 derivatives were described. Some compounds showed selective inhibitory activities for PDE 4 derived from human peripheral blood cells and no effect on the other PDE types (1, 2, 3, 5). The inhibition of the tumor necrosis factor-alpha (TNF-alpha) release in vitro and the carrageenan-induced pleurisy in rats were also described.
- Takayama, Kazuhisa,Iwata, Masahiro,Hisamichi, Hiroyuki,Okamoto, Yoshinori,Aoki, Motonori,Niwa, Akira
-
p. 1050 - 1059
(2007/10/03)
-
- Potential antiarthritic agents. II. Benzoylacetonitriles and β-aminocinnamonitriles
-
Benzoylacetonitrile and β-aminocinnamonitrile are shown to possess potent intiinflammatory activity in the rat adjuvant arthritis model. In a series of phenyl-substituted analogues, only o-, m-, and p-fluorobenzoylacetonitrile and m- and p-fluoro-β-aminocinnamonitrile retained activity. Additionally, β-amino-2- and β-amino-3-thiopheneacrylonitrile and β-oxo-2- and β-oxo-3-thiophenepropionitrile exhibited similar activity. These agents are not believed to be acting via prostaglandin synthetase inhibition. The metabolic profile of benzoylacetonitrile is also described.
- Ridge,Hanifin,Harten,Johnson,Menschik,Nicolau,Sloboda,Watts
-
p. 1385 - 1389
(2007/10/09)
-