- Synthesis, photochemistry, DNA cleavage/binding and cytotoxic properties of fluorescent quinoxaline and quinoline hydroperoxides
-
Novel fluorescent quinoxaline and quinoline hydroperoxides were shown to perform dual role as both fluorophores for cell imaging and photoinduced DNA cleaving agents. Photophysical studies of newly synthesized quinoxaline and quinoline hydroperoxides showed that they all exhibited moderate to good fluorescence. Photolysis of quinoxaline and quinoline hydroperoxides in acetonitrile using UV light above 350 nm resulted in the formation of corresponding ester compounds via γ-hydrogen abstraction by excited carbonyl chromophore. Single strand DNA cleavage was achieved on irradiation of newly synthesized hydroperoxides by UV light (≥350 nm). Both hydroxyl radicals and singlet oxygen were identified as reactive oxygen species (ROS) responsible for the DNA cleavage. Further, we showed quinoline hydroperoxide binds to ct-DNA via intercalative mode. In vitro biological studies revealed that quinoline hydroperoxide has good biocompatibility, cellular uptake property and cell imaging ability. Finally, we showed that quinoline hydroperoxide can permeate into cells efficiently and may cause cytotoxicity upon irradiation by UV light.
- Chowdhury, Nilanjana,Gangopadhyay, Moumita,Karthik,Pradeep Singh,Baidya, Mithu,Ghosh
-
-
Read Online
- Formal hydride transfer mechanism for photoreduction of 3-phenylquinoxalin-2-ones by amines. Association of 3-phenylquinoxalin-2-one with aliphatic amines
-
The photophysical and photochemical behavior of 1-methyl-3-phenylquinoxalin-2-one (MeNQ) and 3-phenylquinoxalin-2-one (HNQ) in the presence of amines is reported. While HNQ fluorescence shows an auxochromic effect and a bathochromic shift with added amine
- De la Fuente,Canete,Zanocco,Saitz,Jullian
-
-
Read Online
- Synthesis of Novel Drug-Like Small Molecules Based on Quinoxaline Containing Amino Substitution at C-2
-
A series of novel "drug-like" small molecules based on quinoxaline containing amino substitution at C-2 were synthesized. All these molecules were prepared either via the reaction of 2-phenyl-3-(piperazin-1-yl)quinoxaline with acyl bromides or benzyl bromides or various carboxylic acids or via the reaction of 2-chloro-3-phenylquinoxaline with various amines. The structures of these novel compounds were confirmed by spectral analysis. The strategy used is simple and efficient and afforded good yields of quinoxaline derivatives.
- Rao, K. Raghavendra,Raghunadh, Akula,Mekala, Ramamohan,Meruva, Suresh Babu,Ganesh, K. Ravi,Krishna,Kalita, Dipak,Laxminarayana, Eppakayala,Pal, Manojit
-
-
Read Online
- Tris(pentafluorophenyl)borane-Catalyzed Oxygen Insertion Reaction of α-Diazoesters (α-Diazoamides) with Dimethyl Sulfoxide
-
A tris(pentafluorophenyl)borane-catalyzed oxidation reaction of α-diazoesters (α-diazo amides) with dimethyl sulfoxide has been developed. The reaction proceeds under metal free conditions to afford a series α-ketoesters and α-ketoamides. The synthetic utility of this protocol is demonstrated through synthetic transformations and scaled-up synthesis. (Figure presented.).
- Gao, Wen-Xia,Liu, Miao-Chang,Wu, Hua-Yue,Wu, Xiao-Yang,Zhou, Yun-Bing
-
supporting information
(2022/01/19)
-
- Visible-light-induced C[sbnd]H arylation of quinoxalin-2(1H)-ones in H2O
-
An efficient visible-light-induced C[sbnd]H arylation of quinoxalin-2(1H)-ones in H2O is developed, which has the advantages of mild reaction conditions, environmental friendliness and good functional group tolerance. This strategy provides a s
- Bao, Hanyang,Lin, Ziyun,Jin, Mengshi,Zhang, Hongdou,Xu, Jun,Chen, Bajin,Li, Wanmei
-
supporting information
(2021/02/16)
-
- DABCO mediated one pot synthesis of sulfoxonium ylides under blue LED
-
DABCO mediated practical and convenient one pot method has been developed to access sulfoxonium ylides under photoredox and metal free conditions at room temperature. The protocol explored the reactivity of DMSO and α-aryl-α-diazo esters in presence of DABCO under blue LED condition. We demonstrated the generality of this protocol by synthesizing a variety of sulfoxonium ylides in very good yields. The practicality of the protocol has been demonstrated by the gram scale synthesis as well as by the extension of this protocol to synthesize precursors of biologically active compounds. This straightforward and practical method offers an alternative route to access very useful sulfoxonium ylides from α-aryl-α-diazoacetates.
- Khade, Vikas V.,Thube, Archana S.,Warghude, Prakash K.,Bhat, Ramakrishna G.
-
-
- α-Keto Acids as Triggers and Partners for the Synthesis of Quinazolinones, Quinoxalinones, Benzooxazinones, and Benzothiazoles in Water
-
A general and efficient method for the synthesis of quinazolinones, quinoxalinones, benzooxazinones, and benzothiazoles from the reactions of α-keto acids with 2-aminobenzamides, benzene-1,2-diamines, 2-aminophenols, and 2-aminobenzenethiols, respectively, is described. The reactions were conducted under catalyst-free conditions, using water as the sole solvent with no additive required, and successfully applied to the synthesis of sildenafil. More importantly, these reactions can be conducted on a mass scale, and the products can be easily purified through filtration and washing with ethanol (or crystallized).
- Huang, Jian,Chen, Wei,Liang, Jiazhi,Yang, Qin,Fan, Yan,Chen, Mu-Wang,Peng, Yiyuan
-
p. 14866 - 14882
(2021/10/25)
-
- Aryl acyl peroxides for visible-light induced decarboxylative arylation of quinoxalin-2(1: H)-ones under additive-, metal catalyst-, and external photosensitizer-free and ambient conditions
-
Aryl radicals were generated for the first time from cheap and easily available aryl acyl peroxides in eco-friendly ethyl acetate under ambient conditions and visible-light illumination in the absence of any additive, metal catalyst, or external photosensitizer. The present arylation of quinoxalin-2(1H)-ones was chemo- and regioselective, and provided good access to various 3-arylquinoxalin-2(1H)-ones. This journal is
- Xie, Long-Yong,Peng, Sha,Yang, Li-Hua,Peng, Cun,Lin, Ying-Wu,Yu, Xianyong,Cao, Zhong,Peng, Yu-Yu,He, Wei-Min
-
supporting information
p. 374 - 378
(2021/01/28)
-
- K2S2O8 mediated C-3 arylation of quinoxalin-2(1H)-ones under metal-, photocatalyst- And light-free conditions
-
Two facile and effective C-3 arylation protocols of quinoxalin-2(1H)-ones with arylhydrazines and aryl boronic acids respectively via free radical cross-coupling reactions under metal-, photocatalyst- and light-free conditions have been unveiled. K2
- Dutta, Nibedita Baruah,Bhuyan, Mayurakhi,Baishya, Gakul
-
p. 3615 - 3624
(2020/02/06)
-
- Compound containing fused ring structure and application thereof, and organic electroluminescent device (by machine translation)
-
The invention relates to the field, of organic electroluminescent devices, and discloses a compound containing a fused ring structure and application thereof, and an organic electroluminescent device, which has a suitable (I) energy level, level HOMO and
- -
-
Paragraph 0113-0115; 0136-0138
(2020/05/30)
-
- Direct decarboxylative C[sbnd]H 3-arylation of quinoxalin-2(H)-ones with aryl acyl peroxides leading to 3-arylquinoxalin-2(1H)-ones
-
A facile and direct decarboxylative C[sbnd]H 3-arylation of quinoxalin-2(H)-ones with aryl acyl peroxides has been developed for the synthesis of 3-arylquinoxalin-2(1H)-ones under simple heating conditions. The present methodology provides a simple and highly efficient approach to various 3-arylquinoxalin-2(1H)-ones in high yields without the use of any catalyst and additives.
- Bao, Pengli,Lv, Yufen,Wei, Wei,Yue, Huilan
-
supporting information
(2020/11/02)
-
- A niobium-catalyzed coupling reaction of α-keto acids with: Ortho -phenylenediamines: Synthesis of 3-arylquinoxalin-2(1 H)-ones
-
A general methodology to access valuable 3-arylquinoxalin-2(1H)-ones was developed, by the reaction of α-keto acids with ortho-phenylenediamines in the presence of ammonium niobium oxalate (ANO) as a catalyst. The reactions were conducted in only 10 min under ultrasonic irradiation as an alternative energy source, affording water as the only co-product. A total of twenty-three different 3-arylquinoxalin-2(1H)-ones were selectively obtained in good to excellent yields by this atom-efficient protocol. Additionally, 1H-15N HMBC experiments were used to reveal the regioisomerism of the obtained products.
- Ebersol, Camila,Rocha, Nicole,Penteado, Filipe,Silva, Márcio S.,Hartwig, Daniela,Lenard?o, Eder J.,Jacob, Raquel G.
-
p. 6154 - 6160
(2019/11/20)
-
- Electrochemical Cross-Coupling of C(sp2)?H with Aryldiazonium Salts via a Paired Electrolysis: an Alternative to Visible Light Photoredox-Based Approach
-
Photoredox-based C?H bond functionalization constitutes one of the most powerful and atom-economical approaches to organic syntheses. During this type of reaction, single electron transfer takes place between the photocatalyst (PC) and redox- active substrates. Electrosynthesis also involves electron transfer between substrates and electrodes. In this paper, we focus upon electrochemical cross-coupling of C(sp2)?H with aryldiazonium salts and have developed an efficient electrochemical approach to the Minisci-type arylation reaction. The constant current paired electrosynthesis proceeds in a simple undivided cell without external supporting electrolyte, features a wide range of substrates and is easy to scale-up. These results demonstrate that photoredox-based cross-coupling of C(sp2)?H with aryldiazonium salts can also proceed successfully under paired electrolysis conditions, thereby contributing to understanding of the parallels between photosynthesis and electrosynthesis. (Figure presented.).
- Jiang, Yang-ye,Dou, Gui-yuan,Zhang, Luo-sha,Xu, Kun,Little, R. Daniel,Zeng, Cheng-chu
-
p. 5170 - 5175
(2019/11/13)
-
- Preparation of Organic Nitrates from Aryldiazoacetates and Fe(NO3)3·9H2O
-
A thermal protocol is reported for the formal insertion of nitric acid into aryldiazoacetates using Fe(NO3)3·9H2O. This strategy is mild and high yielding and allows the preparation of a large variety of members of an unprecedented family of organic nitrates. The nitrate group can be also readily transformed into other functional groups and heterocyclic moieties and can possibly allow new biological explorations of untapped potential associated with their NO-releasing ability.
- Thurow, Samuel,Fernandes, Alessandra A. G.,Quevedo-Acosta, Yovanny,De Oliveira, Matheus F.,De Oliveira, Marcelo G.,Jurberg, Igor D.
-
p. 6909 - 6913
(2019/09/12)
-
- Ambient and aerobic carbon-carbon bond cleavage toward α-ketoester synthesis by transition-metal-free photocatalysis
-
The α-oxoesterification of the CC double bond in readily available enaminones enabling efficient synthesis of α-ketoesters is developed. The reactions showing general tolerance to the reactions of primary and secondary alcohols proceed well under air via Rose Bengal (RB)-based photocatalysis. Particularly, this mild synthetic method has been discovered to tolerate various polyhydroxylated substrates such as phenolic alcohol, diols and triols with an excellent selectivity of mono-oxoesterification. What is more noteworthy is that α-ketoester functionalized 16-dehydropregnenolone acetate resulting from the elaboration on a natural product has been obtained practically.
- Yu, Qing,Zhang, Yating,Wan, Jie-Ping
-
supporting information
p. 3436 - 3441
(2019/06/24)
-
- Preparation method of quinoxalinone derivatives
-
The invention belongs to the field of organic synthetic chemistry. The invention relates to a preparation method of quinoxalinone derivatives. Specifically, a covalent organic framework material 2D-COF-1 is used as a photocatalyst; and the quinoxaline-2 (
- -
-
Paragraph 0069-0072
(2019/12/02)
-
- Mn(OAc)3*2H2O promoted addition of arylboronic acids to quinoxalin-2-ones
-
A simple method has been developed for the synthesis of 3-aryl quinoxalin-2-one derivatives through an oxidative cross-coupling of arylboronic acids with quinoxalin-2-ones using a readily available oxidant Mn(III) acetate dihydrate. This method provides 3-aryl quinoxalin-2-one scaffolds with a broad substrate scope.
- Ramesh, Boora,Reddy, C. Ravikumar,Kumar, G. Ravi,Reddy, B.V. Subba
-
supporting information
p. 628 - 631
(2018/01/17)
-
- Transition Metal-Free Iodosobenzene-Promoted Direct Oxidative 3-Arylation of Quinoxalin-2(H)-ones with Arylhydrazines
-
A transition metal-free iodosobenzene-promoted direct oxidative 3-arylation of quinoxalin-2(H)-ones was developed using various arylhydrazines under air. The protocol affords a variety of 3-arylquinoxalin-2(H)-one derivatives in moderate to good yields. This method provides a rapid access to biologically interesting benzo[g]quinoxalinones and pyrido[3,4-b]pyrazinones. The present methodology features high functional group tolerance including base-sensitive groups as well as allyl- and benzyl-substituted quinoxalin-2(H)-ones under mild reaction conditions. (Figure presented.).
- Paul, Sanjay,Ha, Ji Hyeon,Park, Ga Eul,Lee, Yong Rok
-
supporting information
p. 1515 - 1521
(2017/05/05)
-
- High-Potency Phenylquinoxalinone Cystic Fibrosis Transmembrane Conductance Regulator (CFTR) Activators
-
We previously identified phenylquinoxalinone CFTRact-J027 (4) as a cystic fibrosis transmembrane conductance regulator (CFTR) activator with an EC50 of ~200 nM and demonstrated its therapeutic efficacy in mouse models of constipation. Here, structure-activity studies were done on 36 synthesized phenylquinoxalinone analogs to identify compounds with improved potency and altered metabolic stability. Synthesis of the phenylquinoxalinone core was generally accomplished by condensation of 1,2-phenylenediamines with substituted phenyloxoacetates. Structure-activity studies established, among other features, the privileged nature of a properly positioned nitro moiety on the 3-aryl group. Synthesized analogs showed improved CFTR activation potency compared to 4 with EC50 down to 21 nM and with greater metabolic stability. CFTR activators have potential therapeutic indications in constipation, dry eye, cholestatic liver diseases, and inflammatory lung disorders.
- Son, Jung-Ho,Zhu, Jie S.,Phuan, Puay-Wah,Cil, Onur,Teuthorn, Andrew P.,Ku, Colton K.,Lee, Sujin,Verkman, Alan S.,Kurth, Mark J.
-
p. 2401 - 2410
(2017/04/03)
-
- 1,2,4-triazole derivative having quinoxaline structure, preparation method and application thereof
-
The invention discloses a 1,2,4-triazole derivative having quinoxaline structure, a preparation method and an application thereof. O-nitroaniline and hydrazine hydrate react to form a compound (II). The compound (II) reacts with MBF to prepare a compound
- -
-
Paragraph 0026; 0027
(2017/07/04)
-
- Solid Phase Synthesis of (Benzannelated) Six-Membered Heterocycles via Cyclative Cleavage of Resin-Bound Pseudo-Oxazolones
-
A solid supported procedure for the synthesis of benzoxazinones, dihydropyrazinones, quinoxalinones, and dihydrooxazinones using immobilized oxazolones in combination with difunctional nucleophiles as cleavage agent is presented. The scope of the novel me
- Gr??le, Simone,Vanderheiden, Sylvia,Hodapp, Patrick,Bulat, Bekir,Nieger, Martin,Jung, Nicole,Br?se, Stefan
-
supporting information
p. 3598 - 3601
(2016/08/16)
-
- Application of hydrazone compound containing benzopyrazine structure as bactericide
-
The invention discloses application of a hydrazone compound containing a benzopyrazine structure as a bactericide. A preparation method for the hydrazone compound comprises the following steps: reacting o-nitroaniline with hydrazine hydrate to prepare a c
- -
-
Paragraph 0028
(2017/02/24)
-
- Hydrazone compound containing benzopyrazine structure, and preparation method and application thereof
-
The invention discloses a hydrazone compound containing a benzopyrazine structure, and a preparation method and an application thereof. The preparation method comprises the steps: preparing a compound 1 from o-nitroaniline and hydrazine hydrate; making th
- -
-
Paragraph 0025; 0026
(2017/06/02)
-
- Chemoselective synthesis of 3,6,7-trisubstituted 2-(2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyloxy]- and 2-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)quinoxaline derivatives
-
[Figure not available: see fulltext.] A series of quinoxaline O-nucleosides, 3,6,7-trisubstituted 2-(2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyl-1-yl)quinoxalines and 2-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)quinoxalines, was prepared by the reaction of 3,6,7-trisubstituted quinoxalin-2(1H)-ones with the corresponding protected α-chlorosugars in the presence of NaH. The reaction proceeded chemoselectively to give products of O-substitution with β-configuration at anomeric carbon, as proved by NMR data. The deprotection of the 1-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)quinoxalines was achieved by stirring in ammonia-methanol mixture to afford free O-quinoxaline nucleoside analogs.
- Fathalla, Walid
-
-
- Synthesis of 9,10-substituted 3,4,10,10a-tetrahydro-2H,9H-1-oxa-4a,9- diazaphenanthrenes by reductive cyclization method
-
Commercially available o-phenylenediamine (1) was treated with methyl α-bromo-α-aryl acetate to obtain 3-aryl-3,4-dihydro-1Hquinoxalin- 2-one (2). The latter was reacted with benzyl bromide to obtain 4-benzyl-3-aryl-3,4-dihydro-1H-quinoxalin-2-one (3). Tr
- Rajachandrasekhar,Hariprasad,Venugopala Rao,Venkataiah,Dubey
-
p. 3161 - 3165
(2014/07/22)
-
- Facile One-Pot Synthesis of Benzimidazole and Quinoxalin-2(1 H)-one Scaffolds via Two-Component Coupling Reaction, Deprotection, and Intermolecular Cyclization
-
Two scaffolds, namely benzimidazole and quinoxalin-2(1H)-one, were synthesized by treating 2-(N-Boc-amino)phenylisocyanide (Boc: tert-butoxycarbonyl) with carboxylic acids and glyoxylic acids, respectively. The target compounds were generated directly aft
- Chen, Zhong-Zhu,Tang, Ying,Zuo, Lei,Tang, Dian-Yong,Zhang, Jin,Xu, Zhi-Gang
-
supporting information
p. 2518 - 2520
(2015/07/27)
-
- SUBSTITUTED QUINOXALINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR4
-
The present invention relates to novel quinoxaline derivatives of formula (I) as positive allosteric modulators for modulating metabotropic glutamate receptor subtype 4 (mGluR4) and/or altering glutamate level or glutamatergic signalling.
- -
-
Page/Page column 48
(2014/08/20)
-
- [Ir(P-OP)]-catalyzed asymmetric hydrogenation of diversely substituted C=N-containing heterocycles
-
Iridium(I) complexes of enantiomerically pure phosphine-phosphite ligands ([Ir(Cl)(cod)(P - OP)]) efficiently catalyze the enantioselective hydrogenation of diverse C=N-containing heterocyclic compounds (benzoxazines, benzoxazinones, benzothiazinones, and quinoxalinones; 25 examples, up to 99% ee). A substrate-to-catalyst ratio as high as 2000:1 was reached.
- Nunez-Rico, Jose Luis,Vidal-Ferran, Anton
-
supporting information
p. 2066 - 2069
(2013/06/04)
-
- Asymmetric organocatalytic tandem cyclization/transfer hydrogenation: A synthetic strategy for enantioenriched nitrogen heterocycles
-
An asymmetric organocatalytic tandem reaction comprising cyclization/transfer hydrogenation has been established in a compatible and synergistic way, leading to the step-economical synthesis of enantioenriched tetrahydroquinoxalines and dihydroquinoxalinones from readily accessible materials in excellent enantioselectivity of up to >99% ee. This protocol of a one-operation tandem reaction combines the merits of both tandem reactions and asymmetric organocatalysis, providing an efficient strategy for concisely and enantioselectively synthesizing nitrogen heterocycles with biological relevance. Copyright
- Shi, Feng,Tan, Wei,Zhang, Hong-Hao,Li, Mei,Ye, Qin,Ma, Guan-Hua,Tu, Shu-Jiang,Li, Guigen
-
p. 3715 - 3726
(2014/01/06)
-
- An efficient synthetic protocol for quinoxalinones, Benzoxazinones, and benzothiazinones from 2-oxo-2-aryl-acetyl bromide precursors
-
α-Bromoketones undergo selenium dioxide oxidation to yield reactive 2-oxo-2-arylacetyl bromides that are trapped by aryl-1,2-diamines, 1,2-aminophenol or 1,2-aminothiophenol to give quinoxalinones, benzoxazinones, and benzothiazinones, respectively, in go
- Nagaraj, Muthupandi,Sathiyamoorthy, Sithuraj,Boominathan, Muthusamy,Muthusubramanian, Shanmugam,Bhuvanesh, Nattamai
-
p. 1146 - 1151
(2013/10/21)
-
- Visible-light-induced, copper(i)-catalysed C-N coupling between o-phenylenediamine and terminal alkynes: One-pot synthesis of 3-phenyl-2-hydroxy-quinoxalines
-
Visible-light-initiated aerobic direct C-N coupling between o-phenylenediamines and terminal acetylenes was performed using simple copper(i) chloride as a catalyst for the synthesis of quinoxaline derivatives. The current method works well for a wide range of electron rich as well as electron poor group-substituted o-phenylenediamines and phenylacetylenes. The key component in the reaction is the direct photo-excitation of in situ generated copper arylacetylide (λabs = 420-480 nm). Moreover, as compared to the literature reports (thermal process), the current photochemical method is simple, mild, high yielding, and more viable towards the construction of biologically important quinoxaline derivatives from easily accessible raw materials, without the need of ligands and strong oxidants.
- Sagadevan, Arunachalam,Ragupathi, Ayyakkannu,Hwang, Kuo Chu
-
p. 2110 - 2118
(2013/12/04)
-
- Synthesis and biological evaluation of some novel quinoxaline derivatives as anticonvulsant agents
-
In view of their expected anticonvulsant activity, some new derivatives of quinonxaline (V1-7) were designed and synthesized by condensation of different aromatic aldehydes with 2-(2-oxo-3-phenyl-quinoxalin-1(2H)-yl) acetohydrazide (IV). All sy
- Elhelby, Abdelghany Aly,Ayyad, Rezk Rezk,Zayed, Mohamed Fathalla
-
scheme or table
p. 379 - 381
(2011/10/31)
-
- Revisiting the Hinsberg reaction: Facile and expeditious synthesis of 3-substituted quinoxalin-2(1H)-ones under catalyst-free conditions in water
-
Substituted benzene-1,2-diamine reacted with various α-keto esters at 50° under mild conditions for 15 min using H2O as reaction medium, providing a variety of 3-substituted quinoxalinone derivatives in excellent yields. The reaction was instantaneous, and products were isolated by simple filtration.
- Murthy, Sabbavarapu Narayana,Madhav, Bandaru,Nageswar, Yadavalli Venkata Durga
-
experimental part
p. 1216 - 1220
(2010/08/21)
-
- The first general, highly enantioselective lewis base organocatalyzed hydrosilylation of benzoxazinones and quinoxalinones
-
The first general, highly enantioselective hydrosilylation of benzoxazinones and quinoxalinones has been developed. The chiral Lewis base organocatalysis that are readily accessible from (1S,2R)-ephedrine and (1R,2S)-ephedrine promoted the title reaction to afford various chiral dihydrobenzoxazinones and dihydroquinoxalinones with good yields as well as good enantioselectivities.
- Xue, Zhou-Yang,Jiang, Yan,Peng, Xiao-Zhi,Yuan, Wei-Cheng,Zhang, Xiao-Mei
-
supporting information; experimental part
p. 2132 - 2136
(2010/11/04)
-
- HETEROCYCLIC DERIVATIVES, PHARMACEUTICAL COMPOSITIONS AND METHODS OF USE THEREOF
-
The present invention relates to novel quinoxaline, quinazoline and phthalazine derivatives as well as multimeric derivatives, methods for their preparation, pharmaceutical compositions including such compounds, and methods of using these compounds for the treatment and prevention of brain damage resulting from brain injury, especially secondary brain damage due to traumatic brain injury (TBI). The compounds of the invention are also useful in treating and preventing neurodegenerative diseases.
- -
-
Page/Page column 32
(2010/03/02)
-
- Fragment based design of new H4 receptor-ligands with anti-inflammatory properties in vivo
-
Using a previously reported flexible alignment model we have designed, synthesized, and evaluated a series of compounds at the human histamine H 4 receptor (H4R) from which 2-(4-methyl-piperazin-l-yl)- quinoxaline (3) was identified as a new lead structure for H4R ligands. Exploration of the structure-activity relationship (SAR) of this scaffold led to the identification of 6,7-dichloro 3-(4-methylpiperazin-l-yl) quinoxalin-2(1H)-one (VUF 10214, 57) and 2-benzyl-3-(4-methyl-piperazin-l-yl) quinoxaline (VUF 10148, 20) as potent H4R ligands with nanomolar affinities. In vivo studies in the rat reveal that compound 57 has significant anti-inflammatory properties in the carrageenan-induced paw-edema model.
- Smits, Rogier A.,Lim, Herman D.,Hanzer, Agnes,Zuiderveld, Obbe P.,Guaita, Elena,Adami, Maristella,Coruzzi, Gabriella,Leurs, Rob,De Esch, Iwan J. P.
-
p. 2457 - 2467
(2008/12/22)
-
- HETEROCYCLIC DERIVATIVES BINDING TO THE PERIPHERAL-TYPE BENZODIAZEPINE RECEPTOR (PBR)
-
The present invention relates to novel quinoxaline, quinazoline and phthalazine derivatives as well as multimeric derivatives, methods for their preparation, pharmaceutical compositions including such compounds, and methods of using these compounds for the treatment and prevention of brain damage resulting from brain injury, especially secondary brain damage due to traumatic brain injury (TBI). The compounds of the invention are also useful in treating and preventing neurodegenerative diseases.
- -
-
Page/Page column 67; Sheet 14/26
(2008/06/13)
-
- Quinoxalin-2-one derivatives, compositions which protect useful plants and comprise these derivatives, and processes for their preparation and their use
-
Compounds of the formula (I) and salts thereof in which X is O or S; (Y)n=n substituents Y, n is 0, 1, 2, 3 or 4, R1 is H, OH, NH2, (C1-C4)-alkylamino, di-[(C1-C4)-alkyl]amino or optionally substituted (C1-C10)-alkyl, (C3-C10)-alkenyl, (C3-C10)-alkynyl or (C1-C10)-alkoxy, (C3-C10)-cycloalkyl, (C4-C10)-cycloalkenyl, aryl or heterocyclyl, R2 is H or optionally substituted (C1-C10)-alkyl, (C3-C10)-alkenyl, (C3-C10)-alkynyl, (C3-C10)-cycloalkyl, (C4-C10)-cycloalkenyl, aryl or heterocyclyl, where the radicals Y are as defined in claim 1 are suitable for use as safeners for crop plants or useful plants against the phytotoxic actions of agrochemicals such as pesticides in these plants.
- -
-
Page/Page column 34
(2008/06/13)
-
- Studies of the reactions between indole-2,3-diones (isatins) and 2-aminobenzylamine
-
Reflux of equimolecular amounts 2-aminobenzylamine and isatins in acetic acid produced indolo[3,2-c]quinolin-6-ones in good yields. A proposed mechanism involving initial formation of a spiro compound is given. This isolable intermediate subsequently rearranges via a sequential isocyanate ring opening and a cyclisation process to a urea derivative which finally cyclized to the indolo[3,2-c]quinolin-6-ones. The urea derivative could be prepared separately and cyclized selectively to indolo[3,2-c]quinolin-6-one. Reaction of N-acetylisatin with 2-aminobenzylamine at room temperature yielded the 1,4-benzodiazepinone 3-(2-acetamidophenyl)-1,5-dihydro-1,4-benzodiazepin-2-one whereas its isomer 2(2-acetamidophenyl)-4,5-dihydro-1,4-benzodiazepin-3-one was obtained from 2-(2-acetylaminophenyl)-N-(2-aminobenzyl)-2-oxoacetamide in acetic acid at room temperature. The previously unknown linear isomer of indolo[3,2-c]quinolin-6-one, i.e. indolo[2,3-b]quinolin-11-one, has been prepared by thermal (260°C) cyclization of methyl 2-phenylamino indole-3-carboxylate, which in turn was prepared in two steps from methyl indole-3-carboxylate.
- Bergman, Jan,Engqvist, Robert,St?lhandske, Claes,Wallberg, Hans
-
p. 1033 - 1048
(2007/10/03)
-
- Comparative Kinetic Studies on the Synthesis of Quinoxalinone Derivatives and Pyridopyrazinone Derivatives by the Hinsberg Reaction
-
Kinetic studies on the anelation of quinoxalinone derivatives 3a-c and pyridopyrazinone derivatives 5a-c and 6a-c synthesized by the Hinsberg reaction is reported. o-Phenylenediamine or 2,3-diaminopyridine were treated with bifunctional carbonyl compounds such as glyoxylic, pyruvic and benzoylformic acids under different experimental conditions.When pyridopyrazine derivatives were synthesized both position isomers were achieved applying regioselective reactions.Mixture were avoided by looking for special experimental conditions that led unambigously to only one of the components of the classic "Hinsberg mixture".Quinoxalinone derivatives 3a-c were obtained at room temperature in good yields (>90percent) using anhydrous methanol or ethanol as solvents.On the other hand, only pyridopyrazin-3(4H)-one (5a) was regioselectively attained in aqueous buffer of pH 7 while 3-methylpyridopyrazinone derivatives were regioselectively separated using anhydrous methanol for one isomer, 5b, and anhydrous chloroform for the other isomer, 6b, at room temperature.Yields were higher than 80percent.Reactions with benzoylformic acid did not give good yields and only 2-phenylpyridopyrazin-3(4H)-one (5c) could be obtained using anhydrous chloroform (yield pyrazin-3(4H)-one (5c) in good yields applying this technique.The other isomer, 3-phenylpyrazin-2(1H)-one (6c) was always formed together with the former isomer and could not be isolated from the mixture, when other solvents than chloroform were used as the reaction media.
- Bekerman, Diana G.,Abasolo, Maria Ines,Fernandez, Beatriz M.
-
p. 129 - 133
(2007/10/02)
-
- REARRANGEMENTS OF AROMATIC CARBONYL ARYLHYDRAZONES OF BENZENE, NAPHTHALENE, AND AZULENE
-
Aromatic carbonyl arylhydrazones have been shown to undergo two kinds of rearrangement in polyphosphoric acid both involving nitrogen-nitrogen bond cleavage.The first proceeds via insertion of the imine portion in the position ortho to the second nitrogen atom to give o-phenylenediamine intermediates: their evolution depends on the nature of the starting substrate.This reaction has been employed for synthesizing the quinoxalines (5) and the phenanthridines (11), and was demonstrated to be intramolecular.The second reaction path is a sigmatropic rearrangment exclusive to electron-rich aromatic carbonyl hydrazones.
- Benincori, Tiziana,Pagani, Silvia Bradamante,Fusco, Raffaello,Sannicolo, Franco
-
p. 2721 - 2728
(2007/10/02)
-
- SYNTHESIS AND REACTIONS OF 3-PHENYL-3,4-DIHYDRO-1,4-QUINOXALIN-2(1H)-ONE AND ITS HETEROCYCLIC ANALOGUES
-
The lactams quinoxalinone 3a, benzothiazinone 3b and benzothiazinone 3c were synthesized by reactions of methyl 2-bromo-2-phenylethanoate 1 with orthosubstituted arylamines 2a-2c.Subsequent reductive alkylation of the lactams with sodium hydride and iodom
- Olagbemiro, T.O.,Nyakutse, C.A.,Lajide, L.,Agho, M.O.,Chukwu, C.E.
-
p. 473 - 480
(2007/10/02)
-