426214-12-2Relevant articles and documents
Palladium-Catalyzed Annulation of Arylbenzamides with Diaryliodonium Salts
Pan, Cheng,Wang, Limin,Han, Jianwei
supporting information, p. 268 - 273 (2021/11/09)
By using diaryliodonium salts, a cylization has been accomplished in the synthesis of N-aryl phenanthridinone derivatives via a cascade of ortho-arylation and Csp2-N bond formation in the presence of palladium catalyst. The reaction exhibits a broad compatibility of readily available N-arylnaphthamides. (Figure presented.).
Preparation and biological properties of ring-substituted naphthalene-1-carboxanilides
Gonec, Tomas,Kos, Jiri,Nevin, Eoghan,Govender, Rodney,Pesko, Matus,Tengler, Jan,Kushkevych, Ivan,Stastna, Vendula,Oravec, Michal,Kollar, Peter,O'mahony, Jim,Kralova, Katarina,Coffey, Aidan,Jampilek, Josef
, p. 10386 - 10409 (2014/08/05)
In this study, a series of twenty- Two ring-substituted naphthalene-1- carboxanilides were prepared and characterized. Primary in vitro screening of the synthesized carboxanilides was performed against Mycobacterium avium subsp. paratuberculosis. N-(2-Methoxyphenyl)naphthalene-1-carboxamide, N-(3-methoxyphenyl) naphthalene-1-carboxamide, N-(3-methylphenyl)naphthalene-1- carboxamide, N-(4-methylphenyl)naphthalene-1-carboxamide and N-(3-fluorophenyl)naphthalene-1- carboxamide showed against M. avium subsp. paratuberculosis two-fold higher activity than rifampicin and three-fold higher activity than ciprofloxacin. The most effective antimycobacterial compounds demonstrated insignificant toxicity against the human monocytic leukemia THP-1 cell line. The testing of biological activity of the compounds was completed with the study of photosynthetic electron transport (PET) inhibition in isolated spinach (Spinacia oleracea L.) chloroplasts. The PET-inhibiting activity expressed by IC50 value of the most active compound N-[4-(trifluoromethyl)phenyl]naphthalene-1- carboxamide was 59 μmol/L. The structure- Activity relationships are discussed.
Pd(OAc)2-catalyzed carbonylative coupling of aryl iodide with ortho-haloamines in water
Tambade, Pawan J.,Patil, Yogesh P.,Qureshi, Ziyauddin S.,Dhake, Kishor P.,Bhanage, Bhalchandra M.
supporting information; experimental part, p. 176 - 185 (2011/10/31)
The carbonylative cross coupling of aryl iodide with ortho-haloaniline to ortho-haloanilide using phosphine-free Pd(OAc)2 catalyst in water as a reaction medium has been studied. The present protocol facilitated the reaction of o-haloanilines with a wide variety of hindered and functionalized aryl iodides, affording good yields of the desired products. The protocol was also extended for the synthesis of benzoxazoles through cyclization of ortho-haloanilide using Cu(acac)2 catalyst. Taylor & Francis Group, LLC.
PC-N-Heterocycles: Synthesis of biaryl-type 1,3-benzazaphospholes with ortho-substituted phenyl or 2-heteroaryl groups
Aluri, Bhaskar Reddy,Niaz, Basit,Kindermann, Markus K.,Jones, Peter G.,Heinicke, Joachim
experimental part, p. 211 - 224 (2011/02/16)
A facile synthesis of functionally substituted 2-(hetero)aryl 1,3-benzazaphospholes via nickel- or palladium-catalyzed phosphonylation of N-acyl-2-bromoanilides 1a-k with triethyl phosphite is presented. Anilidophosphonates 2a-g with naphthoyl-, o-substituted phenyl, furoyl- or thenoyl groups allow direct reductive cyclization with LiAlH4 to benzazaphospholes 3. The reaction of the o-bromoderivative 2d proceeds with concomitant replacement of bromine by hydrogen, whereas the electron-withdrawing pyridyl group of 2h prevents the synthesis of 3h by this short route. An alternative synthesis of 2-pyridylbenzazaphosphole 3hvia anilidophosphonates succeeded starting from Fmoc-anilinophosphonate 2kvia selective cleavage of the N-protecting group, reduction of the resulting phosphonoaniline to phosphinoaniline and cyclization with pyridine-2-carboxaldehyde via a dihydrobenzazaphosphole 8. N-Substituted pyridylmethylbenzazaphosphole 9 was detected as a side product. The structure elucidation of the new compounds is based on multinuclear NMR data and X-ray crystal structure analyses of a phosphonoanilide, underlining the dominance of N-H...OP hydrogen bonds over N-H...OC type hydrogen bonds, of 3h and a supramolecular associate of 3b and its unprecedented air oxidation product 10.
Structural development studies of anti-hepatitis C virus agents with a phenanthridinone skeleton
Nakamura, Masahiko,Aoyama, Atsushi,Salim, Mohammed T.A.,Okamoto, Mika,Baba, Masanori,Miyachi, Hiroyuki,Hashimoto, Yuichi,Aoyama, Hiroshi
scheme or table, p. 2402 - 2411 (2010/06/20)
A phenanthridinone skeleton was derived from our previous researches on thalidomide and retinoids as a multi-template for generation of anti-viral lead compounds. Structural development studies focusing on anti-hepatitis C virus activity afforded 5-butyl-2-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenanthridin-6(5H)-one (10) and 5-butylbenzo[b]phenanthridin-6(5H)-one (39), which showed EC50 values of approximately 3.7 and 3.2 μM, respectively.
