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Discovery of Novel Polycyclic Heterocyclic Derivatives from Evodiamine for the Potential Treatment of Triple-Negative Breast Cancer
Evodiamine (Evo) is a quinazolinocarboline alkaloid found in Evodia rutaecarpa and exhibits moderate antiproliferative activity. Herein, we report using a scaffold-hopping approach to identify a series of novel polycyclic heterocyclic derivatives based on Evo as the topoisomerase I (Top1) inhibitor for the treatment of triple-negative breast cancer (TNBC), which is an aggressive subtype of breast cancer with limited treatment options. The most potent compound 7f inhibited cell growth in a human breast carcinoma cell line (MDA-MB-231) with an IC50 value of 0.36 μM. Further studies revealed that Top1 was the target of 7f, which directly induced irreversible Top1-DNA covalent complex formation or induced an oxidative DNA lesion through an indirect mechanism mediated by reactive oxygen species. More importantly, in vivo studies showed that 7f exhibited potent antitumor activity in a TNBC-patient-derived tumor xenograft model. These results suggest that compound 7f deserves further investigation as a promising candidate for the treatment of TNBC.
Chen, Zhe-Sheng,Li, Dahong,Qiu, Yangyi,Wu, Liang,Xu, Jinyi,Xu, Shengtao,Yang, Dong-Hua,Yao, Hong,Zhou, Manzhen
p. 17346 - 17365
(2021/12/09)

Palladium-Catalyzed Multistep Tandem Carbonylation/N-Dealkylation/Carbonylation Reaction: Access to Isatoic Anhydrides
A novel and efficient synthesis of isatoic anhydride derivatives was developed via palladium-catalyzed multistep tandem carbonylation/N-dealkylation/carbonylation reaction with alkyl as the leaving group and tertiary anilines as nitrogen nucleophiles. This approach features good functional group compatibility and readily available starting materials. Furthermore, it provided a convenient approach for the synthesis of biologically and medicinally useful evodiamine.
Wang, Shoucai,Li, Xuan,Zang, Jiawang,Liu, Meichen,Zhang, Siyu,Jiang, Guangbin,Ji, Fanghua
p. 2672 - 2679
(2020/02/04)

Synthesis and docking studies of a novel tetrahydroquinazoline derivative as promising scaffold for acetylcholine esterase inhibition
Alzheimer's disease (AD) is one of the most prevalent neurodegenerative disorders. While pathological hallmarks of this disorder are known, the exact cause of AD remains unclear. Quinazoline was found to be a promising scaffold for the design and developm
Alsuhaimat, Rawan A.,Abualassal, Qais,Abudayeh, Zead Helmi,Ebada, Sherif S.,Albohy, Amgad
p. 4797 - 4804
(2020/12/25)

Synthesis, biological screening, and molecular docking of quinazolinone and quinazolinethione as phosphodiesterase 7 inhibitors
N-Substituted isatoic anhydrides were used as starting materials for the synthesis of compounds 5–16 through alkali hydrolysis, Schiff base reactions, and oxidation. Compounds 18–23 were obtained by thionation of their oxo isosteres using Lawesson's reage
Elfeky, Sherin M.,Sobahi, Tariq R.,Gineinah, Magdy M.,Ahmed, Nesreen S.
(2019/11/16)

Naryl-substituted anthranilamides with intramolecular hydrogen bonds
Hydrogen bonding interaction as one type of non-covalent force has proven itself to be highly efficient for constructing structurally unique artificial secondary structures. Here, the structure of Naryl-substituted anthranilamide in solution is demonstrated by various NMR technique, the intramolecular hydrogen bonds between amide attached to arylamine of the same ring is proposed, which is supported by its crystal structure in the solid phase. The substituent on the nitrogen atom of arylamine plays an important role in forming the presence of intramolecular hydrogen bonds. The chemical shift of the Naryl-H downfield changes obviously, due to the formation of intramolecular hydrogen bonds and the deshielding effect of oxygen, and the neighboring C-H is activated and shows downfield protonic signal too. The presence of intramolecular hydrogen bonds probably provides the explanation for the transformation from Naryl-substituted anthranilamide to imine, which could be converted into 2-aryl quinazolinone finally.
Wang, Li-Xia,Hu, Ben-Quan,Xiang, Jun-Feng,Cui, Jie,Hao, Xiang,Liang, Tong-Ling,Tang, Ya-Lin
supporting information
p. 8588 - 8591
(2014/12/11)

Metal-free oxidative synthesis of quinazolinones via dual amination of sp3 C-H bonds
A novel metal-free synthesis of quinazolinones via dual amination of sp3 C-H bonds was developed. The sp3 carbon in methylarenes or adjacent to a heteroatom in DMSO, DMF or DMA was used as the one carbon synthon. This journal is the Partner Organisations 2014.
Zhao, Dan,Wang, Teng,Li, Jian-Xin
p. 6471 - 6474
(2014/06/09)

New nucleophilic rearrangement in the mechanism of the three-component domino cyclisation affording fluoroalkylated (pyrrolo)quinazolines
The following mechanism steps were verified for the three-component domino cyclisation affording (pyrrolo)quinazolines from 2-(aminomethyl)aniline, a very reactive oxo compound and "usual" oxo compound. The first step was a rapid reaction of very reactive oxo compound (trifluoropyruvate or hexafluoroacetone) with benzylic amino group to form hemiaminal, but not imine; the second step was the reaction of oxo compound with aromatic amino group to form imine (Schiff base) being in equilibrium with its enamine form; the third step was an intramolecular attack of the hemiaminal carbon by the enamine carbon followed by a new nucleophilic rearrangement to form tetrahydropyrimidine cycle; the forth step was closure of the lactam ring, if ester group was available as in trifluoropyruvate.2013 Elsevier B.V. All rights reserved.
Paleta, Old?ich,Dolensky, Bohumil,Pale?ek, Ji?í,Kví?ala, Jaroslav
supporting information
p. 1 - 11
(2014/01/06)

Three-component (Domino) reaction affording substituted pyrroloquinazolines: Cyclization regioselectivity and stereoselectivity
The cyclization involving 2-(aminomethyl)aniline, methyl 3,3,3-trifluoropyruvate, and various oxo compound afforded linearly annulated pyrroloquinazolines, for example, (2R,3aS)-2-hydroxy-3a-phenyl-2- trifluoromethyl-3,3a,4,9-tetrahydropyrrolo[2,1-b]quina
Paleta, Oldrich,Dolensky, Bohumil,Palecek, Jiri,Kvicala, Jaroslav
supporting information
p. 1262 - 1270
(2013/04/10)

Palladium-catalyzed regioselective carbonylation of C-H bonds of N -alkyl anilines for synthesis of isatoic anhydrides
A Pd-catalyzed regioselective C-H bond carbonylation of N-alkyl anilines for the synthesis of isatoic anhydrides has been developed. The key Pd-catalyst intermediate has been isolated and characterized. This novel Pd-catalyzed carbonylation reaction tolerates a wide range of functional groups and is a reliable method for the rapid elaboration of readily available N-alkyl anilines into a variety of substituted isatoic anhydrides under mild conditions.
Guan, Zheng-Hui,Chen, Ming,Ren, Zhi-Hui
p. 17490 - 17493,4
(2020/09/16)

2-Arylaminopyrimidine derivatives as PLK inhibitors
Anilino-pyrimidine and 1,2,4-triazine compounds (1) are new. Anilino-pyrimidine and 1,2,4-triazine compounds of formula (1), their tautomers, racemates, enantiomers and/or diastereomers and acid-addition salts are new. X : NR 1a>, O or S; Y : CH or N; Z : hydrogen, halo, (halo)1-3C alkyl, 2-3C alkenyl, 2-3C alkynyl, formyl, 1-3C (halo)alkylcarbonyl, 2-3C alkenyl-, 2-3C alkynyl-carbonyl or pseudohalo; A : (hetero)aryl group (i) or (ii); R a> - R f>e.g. hydrogen, halo or nitro; R 1> and R 1a>hydrogen or methyl; R 2>e.g. Cl, Br, I, OR 6>; R 3>e.g. -CONR 1>-L-Q 3-Q 4-R 9>, -NR 1>-CO-L-Q 3-Q 4-R 9>; R 4>e.g. OR 6>, COR 6>, CONR 6>R 7>, NR 6>R 7>, NR 6>COR 7>, NR 6>SO 2R 7>, N=CR 6>R 7>, SR 6>, SOR 6>, SO 2R 6>, SO 2NR 6>R 7> or pseudohalogen, or any of 1-8C alkyl, 2-10C alkenyl or alkynyl, 3-8C cycloalkyl, (hetero)aryl or heterocyclyl; R 5>hydrogen, halo, trifluoromethyl, 1-3C alkyl or OR 6>; R 6>, R 7>e.g. hydrogen or any of 1-5C alkyl, 2-5C alkenyl or alkynyl, 3-10C cycloalkyl, (hetero)aryl or heterocyclyl; L : e.g. bond or residue of 1-16C alkyl, 2-16C alkenyl or alkynyl, 3-10C cycloalkyl, (hetero)aryl or heterocyclyl; Q 3 and Q 4bond or a mono- or bi-cyclic heterocyclyl, optionally substituted by one or more of Me, Et, halo, amino, hydroxy or pseudohalo; R 9>as L but not a bond; and T : N, O or S. Full definitions are given in the DEFINITIONS (Full Definitions) field. [Image] [Image] ACTIVITY : Cytostatic; Antiinflammatory; Immunosuppressive; Virucide; Anti-HIV; Dermatological; Nootropic; Neuroprotective; Nephrotropic; Vulnerary; Antibacterial; Fungicide; Antiparasitic; Antipsoriatic; Osteopathic; Cardiovascular-Gen; Vasotropic; Gastrointestinal-Gen. MECHANISM OF ACTION : Kinase inhibitor; Polo-like kinase (PLK) inhibitor. In a trial, (1) was found to have EC 50 against recombinant human PLK1 of below 5, generally 1 mu M. No results for specific compounds were given.
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Page/Page column 43

(2010/02/14)

Mono-N-methylation of functionalized anilines with alkyl methyl carbonates over NaY faujasites. 4. Kinetics and selectivity
(Chemical Equation Presented) In the presence of NaY faujasite as the catalyst, the reaction of bifunctional anilines (1-4: XC6H 4-NH2; X = OH, CO2H, CH2OH, and CONH2) with methyl alkyl carbonates [MeOCO2R′: R′ = Me or MeO(CH2)2O(CH2)2] proceeds with a very high mono-N-methyl selectivity (XC6H 4NHMe up to 99%), and chemoselectivity as well, with other nucleophilic functions (OH, CO2H, CH2OH, CONH2) fully preserved from alkylation and/or transesterification reactions. Aromatic substituents, however, modify the relative reactivity of amines 1-4: good evidence suggests that, not only steric and electronic effects, but, importantly, direct acid-base interactions between substituents and the catalyst are involved. Weakly acidic groups (OH, CH2OH, CONH2, pKa ≥ 10) may help the reaction, while aminobenzoic acids (pK a of 4-5) are the least reactive substrates. The solvent polarity also affects the reaction, which is faster in xylene than in the more polar diglyme. The mono-N-methyl selectivity is explained by the adsorption pattern of reagents within the zeolite pores: a BAl2 displacement of the amine on methyl alkyl carbonate should occur aided by the geometric features of the NaY supercavities. Different factors account for the reaction chemoselectivity. Evidence proves that the polarizability of the two nucleophilic terms (NH 2 and X groups) of anilines is relevant, although adsorption and confinement phenomena of reagents promoted by the zeolite should also be considered.
Selva, Maurizio,Tundo, Pietro,Foccardi, Tommaso
p. 2476 - 2485
(2007/10/03)

Alkylamino derivatives of 4-aminomethylpyridine as inhibitors of copper-containing amine oxidases
The first substratelike, reversible inhibitors of different copper amine oxidases (CAOs) with IC50 (M) as low as 2.0 × 10-8 corresponding to derivatives of 4-aminomethylpyridine with alkoxy (1a-d), alkylthio (2a,b), and alkylamino (3
Bertini, Vincenzo,Buffoni, Franca,Ignesti, Giovanni,Picci, Nevio,Trombino, Sonia,Iemma, Francesca,Alfei, Silvana,Pocci, Marco,Lucchesini, Francesco,De Munno, Angela
p. 664 - 670
(2007/10/03)

Synthesis of mono-N-substituted functionalized anilines
The present invention relates to a process for direct and selective synthesis of mono-N-substituted functionalized anilines by using alkylating agents selected from the class of organic carbonates, preferably of the dialkyl, dibenzyl and diallyl types, in the presence of suitable catalysts that are chemically related to the class of aluminosilicates.
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Page 4

(2008/06/13)

Synthesis of mono-N-substituted functionalized anilines
The present invention relates to a process for direct and selective synthesis of mono-N-substituted functionalized anilines by using alkylating agents selected from the class of organic carbonates, preferably of the dialkyl, dibenzyl and diallyl types, in the presence of suitable catalysts that are chemically related to the class of aluminosilicates.
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Page 7

(2008/06/13)

Reaction of functionalized anilines with dimethyl carbonate over NaY faujasite. 3. Chemoselectivity toward mono-N-methylation
In the presence of NaY faujasite, dimethyl carbonate (MeOCO2Me, DMC) is a highly chemoselective methylating agent of functionalized anilines such as aminophenols (1), aminobenzyl alcohols (2), aminobenzoic acids (3), and aminobenzamides (4). The reaction proceeds with the exclusive formation of N-methylanilines without any concurrent O-methylation or N-/O-methoxy carbonylation side processes. Particularly, only mono-N-methyl derivatives [XC6H4NHMe, X = o-, m-, and p-OH; o- and p-CH 2OH; o- and P-CO2H; o- and p-CONH2] are obtained with selectivity up to 99% and isolated yields of 74-99%. DMC, which usually promotes methylations only at T > 120 °C, is activated by the zeolite catalyst and it reacts with compounds 1, 2, and 4, at 90 °C. Aminobenzoic acids (3) require a higher reaction temperature (≥130 °C).
Selva, Maurizio,Tundo, Pietro,Perosa, Alvise
p. 7374 - 7378
(2007/10/03)

Alkylation process for preparing azetidinone compound and starting compound therefor
Novel process for preparing azetidinone compound of the formula [III]: STR1 wherein R1 is H or lower alkyl, R2 and R3 combine together with the adjacent nitrogen to form heterocyclic group, and R4 is protected or unprotected hydroxy-substituted lower alkyl, which comprises reacting an alkanamide compound of the formula [I]: STR2 wherein R1, R2 and R3 are the same as defined above, with a compound of the formula [II]: STR3 wherein L1 is a leaving group and R4 is the same as defined above, in the presence of a base, said compound [III] being useful as synthetic intermediate for 1-methylcarbapenem derivative having excellent antibacterial activity.
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(2008/06/13)

Azetidinone compound and process for preparation thereof
There is disclosed an azetidinone compound of the formula [I]: STR1 wherein Ring B is a benzene ring which may have substituent(s), R1 is a hydroxy-substituted lower alkyl group which may have substituent(s), X is oxygen atom and the like, Y is oxygen atom and the like, and Z is a methylene group which may have substituent(s), which is useful as a synthetic intermediate of the 1β-methylcarbapenem-type antibacterial agent.
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(2008/06/13)

Mechanism of alkaline cyclization of 2-(substituted benzamido)benzamides to 4-quinazolinones
The title amides cyclize rapidly to the corresponding quinazolin-4-ones in aqueous alkaline solution at 25°C; the pseudo-first-order rate constants fit the empirical equation k(obs) = k(max) [OH-]/(K(m) + [OH-] + [OH-]sup
Gardner,Kanagasooriam,Smyth,Williams
p. 6245 - 6250
(2007/10/02)

A simple approach to novel 3-aza-1-dethiacepham analogs
Synthesis of a variety of novel 3-aza-1-dethiacepham analogs (6a-d, 7a-d, 13a-c, 18a, b, 21, 22) via cycloaddition has been described.The reaction of in situ generated ketene and appropriate heterocycles as imine components results in the formation of polycyclic β-lactams.Since thienopyrimidine derivatives have potential biological activity, the main work involves the grafting of β-lactam ring onto these moieties through a simple approach.
Sharma, S D,Kaur, Verinder,Sharma, Pradeep
p. 517 - 525
(2007/10/02)

A Mass Spectral Rearrangement of 2-(Alkylamino)benzoic Acid Derivatives and Related Heterocyclic Systems
The behavior of a series of 2-(alkylamino)benzoic acid derivatives and related heterocyclic systems has been investigated using electron impact mass spectrometry and fragmentation pathways have been formulated.Deuterium-labeled and 13C-labeled compounds w
Barbuch, Robert J.,Peet, Norton P.
p. 816 - 820
(2007/10/02)

A Versatile Synthesis of 3H-1(H),4(H)-Benzodiazepin-2,5-diones
Reaction of isatoic anhydrides (1) and α-amino acids (2) in glacial acetic acid under reflux gave 3H-1(H),4(H)-benzodiazepin-2,5-diones (3) in good yields.These compounds have been characterised by UV, IR, mass, PMR and 13C-NMR spectra.
Mohiuddin, G.,Reddy, P. S. N.,Ahmed, Khalil,Ratnam, C. V.
p. 905 - 907
(2007/10/02)

2,1-Benzisothiazoles. XIII . Intermediates and Products in the Sulfur Extrusion Reaction of 2,1-Benzisothiazolines-3(1H)-one. A New Synthesis of 11H-Pyridoquinazolin-11-one ("Pyracridone")
Triethyl phosphite abstracts sulfur from 2,1-benzisothiazolin-3(1H)-one (1); a reaction intermediate is the spirocyclic compound 11, and products include the benzoxazine 6 and polyanthraniloyl compounds.In the presence of pyridine, pyracridone (13) is formed.The ketene-imine 9 is probably not an intermediate in these reactions.The reactions of other nucleophiles with 1 and with its N-methyl derivative 15, have been examined.
Davis, Michael,Hook, Robert J.,Wu, Wen Yang
p. 369 - 373
(2007/10/02)