34897-85-3Relevant articles and documents
Stereochemical issues related to the synthesis of 7,10-dimethyl- 7,10,16,16a-tetrahydro-11H-quinazolino[2',3':3,4]pyrazino-[1,2-b]β- carboline-5,8-diones
Madrigal, Antonio,Grande, Mercedes,Avendano, Carmen
, p. 3115 - 3123 (1998)
Condensation reactions between anthranilic acid and iminoethers derived from 2,3,6,7,12,12a-hexahydropyrazino[1,2-b]β-carboline-1,4-diones 3-8 to give the title hexacyclic compounds were studied from a stereochemical point of view. The configuration was r
Ruthenium(ii)-catalyzed synthesis of indazolone-fused cinnolines via C-H coupling with diazo compounds
Su, Lin,Yu, Zheng,Ren, Peiling,Luo, Zhi,Hou, Wei,Xu, Hongtao
, p. 7236 - 7244 (2018)
A robust, efficient and scalable method for the synthesis of 12H-indazolo[2,1-a]cinnolin-12-ones was developed. Significantly, a less developed cationic complex [Ru(p-cymene)(MeCN)3(SbF6)2] was found to be effective for th
'Second-generation' 1,2,3-triazole-based inhibitors of: Porphyromonas gingivalis adherence to oral streptococci and biofilm formation
Patil, Pravin C.,Tan, Jinlian,Demuth, Donald R.,Luzzio, Frederick A.
, p. 268 - 279 (2019/03/02)
Several 'second-generation' click inhibitors of the multi-species biofilm propagated by the adherence of the oral pathogen Porphyromonas gingivalis to Streptococcus gordonii were synthesized and evaluated. The design of the structures was based on the results obtained with the first-generation diphenyloxazole 'click' inhibitors which bear suitable hydrophobic and polar groups within a dual scaffold molecule bearing a 1,2,3-triazole spacer. The structures of the synthetic targets reported herein now consist of a triazolyl(phenylsulfonylmethyl) and a triazolyl(phenylsulfinylmethyl) spacer which joins a 4,5-diphenyloxazole with both phenyl rings bearing lipophilic substituents. The triazolyl "linker" group is formed by a click reaction between the 4-azido(phenylsulfonyl/sulfinylmethyl) oxazoles and acetylenic components having aryl groups bearing hydrophobic substituents. The 1,3,5-trisubstituted-2,4,6-triazine scaffold of the most active click compounds were modeled after the structural motif termed the VXXLL nuclear receptor (NR) box. When substituted at the 3- and 5-positions with 2- and 4-fluorophenylamino and N,N-diethylamino units, the candidates bearing the 1,3,5-trisubstituted-2,4,6-triazine scaffold formed a substantial subset of the second-generation click candidates. Four of the click products, compounds 95, 111, 115 and 122 showed inhibition of the adherence of P. gingivalis to S. gordonii with an IC50 range of 2.3-4.3 μM and only 111 exhibited cytotoxic activity against telomerase immortalized gingival keratinocytes at 60 μM. These results suggest that compounds 95, 115, 122, and possibly 111 represent the most suitable compounds to evaluate for activity in vivo.
Synthesis of Diverse Nitrogen Heterocycles via Palladium-Catalyzed Tandem Azide–Isocyanide Cross-Coupling/Cyclization: Mechanistic Insight using Experimental and Theoretical Studies
Ansari, Arshad J.,Pathare, Ramdas S.,Maurya, Antim K.,Agnihotri, Vijai K.,Khan, Shahnawaz,Roy, Tapta Kanchan,Sawant, Devesh M.,Pardasani, Ram T.
, p. 290 - 297 (2017/12/07)
A rapid and elegant tandem azide–isocyanide cross-coupling/cyclization protocol has been developed based on a nitrene transfer reaction. The palladium-catalyzed ligand-free methodology led to the synthesis of three different heterocyclic scaffolds with excellent atom/step/redox economy. Studies based on first-principles-based quantum calculations and control experiments unraveled a concerted process of nitrene transfer reaction on isocyanides, ruling out the metallaaziridine intermediate reported earlier. This finding could pave the way for novel applications of nitrene transfer reactions to generate bioactive heterocycles. (Figure presented.).
Insights into the Desaturation of Cyclopeptin and its C3 Epimer Catalyzed by a non-Heme Iron Enzyme: Structural Characterization and Mechanism Elucidation
Liao, Hsuan-Jen,Li, Jikun,Huang, Jhih-Liang,Davidson, Madison,Kurnikov, Igor,Lin, Te-Sheng,Lee, Justin L.,Kurnikova, Maria,Guo, Yisong,Chan, Nei-Li,Chang, Wei-Chen
supporting information, p. 1831 - 1835 (2018/01/27)
AsqJ, an iron(II)- and 2-oxoglutarate-dependent enzyme found in viridicatin-type alkaloid biosynthetic pathways, catalyzes sequential desaturation and epoxidation to produce cyclopenins. Crystal structures of AsqJ bound to cyclopeptin and its C3 epimer ar
Oxazoles for click chemistry II: Synthesis of extended heterocyclic scaffolds
Patil, Pravin C.,Luzzio, Frederick A.,Demuth, Donald R.
supporting information, p. 3039 - 3041 (2015/05/27)
Abstract New routes to 2,4,5-trisubstituted oxazoles were established whereby the substitution pattern was established by the structure of the starting nonsymmetrical acyloins. 2-Chloromethyl-4, 5-disubstituted oxazoles were prepared by refinements of an earlier described process whereby chloroacetyl esters of symmetrical and nonsymmetrical acyloins were cyclized using an ammonium acetate/acetic acid protocol. After substitution is effected, the azide moiety is then installed by substitution under mild conditions. While dibrominated and iodinated phenyloxazoles are required for further synthetic elaboration, the cyclization reaction was found to be very sensitive to the relative positions of the halogens in the starting materials.
Intramolecular azide to alkene cycloadditions for the construction of pyrrolobenzodiazepines and azetidino-benzodiazepines
Hemming, Karl,Chambers, Christopher S.,Jamshaid, Faisal,O'Gorman, Paul A.
, p. 16737 - 16756 (2015/01/09)
The coupling of proline- and azetidinone-substituted alkenes to 2-azidobenzoic and 2-azidobenzenesulfonic acid gives precursors that undergo intramolecular azide to alkene 1,3-dipolar cycloadditions to give imine-, triazoline- or aziridine-containing pyrr
Azide based routes to tetrazolo and oxadiazolo derivatives of pyrrolobenzodiazepines and pyrrolobenzothiadiazepines
Hemming, Karl,Chambers, Christopher S.,Hamasharif, Muslih S.,Jo?o, Heidi,Khan, Musharraf N.,Patel, Nilesh,Airley, Rachel,Day, Sharn
, p. 7306 - 7317 (2016/02/03)
Tetrazolo- and 1,2,4-oxadiazolo-fused derivatives of the antitumour, antibiotic, DNA-interactive pyrrolo[2,1-c][1,4]benzodiazepines and their pyrrolobenzothiadiazepine derivatives have been produced as analogues of a 1,2,3-triazolo-fused pyrrolobenzothiad
Multicomponent assembly processes for the synthesis of diverse yohimbine and corynanthe alkaloid analogues
Granger, Brett A.,Wang, Zhiqian,Kaneda, Kyosuke,Fang, Zhenglai,Martin, Stephen F.
supporting information, p. 379 - 386 (2013/07/26)
A strategy involving a Mannich-type multicomponent assembly process followed by a 1,3-dipolar cycloaddition has been developed for the rapid and efficient construction of parent heterocyclic scaffolds bearing indole and isoxazolidine rings. These key intermediates were then readily elaborated using well-established protocols for refunctionalization and cross-coupling to access a diverse 180-member library of novel pentacyclic and tetracyclic compounds related to the Yohimbine and Corynanthe alkaloids. Several other new multicomponent assembly processes were developed to access dihydro-β- carboline-fused benzodiazepines, pyrimidinediones, and rutaecarpine derivatives.
Triplex-forming ability of oligonucleotides containing 1-aryl-1,2,3- triazole nucleobases linked via a two atom-length spacer
Hari, Yoshiyuki,Nakahara, Motoi,Obika, Satoshi
, p. 5583 - 5588 (2013/09/02)
Phosphoramidites containing 2-propynyloxy or 1-butyn-4-yl as nucleobase precursors were synthesized and introduced into oligonucleotides using an automated DNA synthesizer. Copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition of the oligonucleotides wi
