cas 32618-85-2, 2,4-DIHYDROXY-6-NITROQUINAZOLINE

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Synthesis, spectroscopic characterization and x-ray analysis of 6-nitroquinazoline-2,4(1H,3H)-dione
In this work, 6-nitroquinazoline-2,4(1H,3H)-dione was obtained in two step with good yields using a facile synthetic method. Its structure was characterized by X-ray single crystal diffraction technique (XRD), IR, 1D-NMR (1H-NMR and 13C-NMR) and 2D-NMR (H-H COSY and H-C HMBC) spectroscopy. All N and O carbonyl atoms are involved in hydrogen bonding, with an average HO distance of 1.89(2) A and N-HO angles in the range 169.5(2)-177.2(2). In the crystal packing the molecules are associated by two strong intermolecular N-HO hydrogen bonds forming centrosymmetric ring with graph-set motif R22(8), which are linked by N-HO hydrogen bonds.
Kesternich, Victor,Perez-Fehrmann, Marcia,Ortiz, Sergio,Verdugo, Felipe,Brito, Ivan,Bolte, Michael,Cardenas, Alejandro
p. 1817 - 1819
(2013)
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Transition metals in organic synthesis, part 111: 1 first total synthesis and structural revision of antipathine A
We describe the first total synthesis of antipathine A and a revision of the original structural assignment. Georg Thieme Verlag Stuttgart, New York.
Berndt, Andreas,Gruner, Margit,Schmidt, Arndt W.,Kn?lker, Hans-Joachim
p. 2102 - 2106
(2013)
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DIACYLGLYCEROL KINASE MODULATING COMPOUNDS
The present disclosure provides diacylglycerol kinase modulating compounds, and pharmaceutical compositions thereof, for treating cancer, including solid tumors, and viral infections, such as HIV or hepatitis B virus infection. The compounds can be used alone or in combination with other agents.
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(2021/07/02)

Synthesis and Anti-Proliferation Activity Evaluation of Novel 2-Chloroquinazoline as Potential EGFR-TK Inhibitors
A novel series of 2-chloroquinazoline derivatives had been synthesized and their anti-proliferation activities against the four EGFR high-expressing cells A549, NCI-H1975, AGS and HepG2 cell lines were evaluated. The preliminary SAR study of the scaffold of new compounds showed that the compounds with a chlorine substituent on R3 had a better anti-proliferation activity than those substituted by hydrogen atom or vinyl group. Among them, 2-chloro-N-[2-chloro-4-(3-chloro-4-fluoroanilino)quinazolin-6-yl]acetamide (10b) had the best activity, and the corresponding IC50 were 3.68, 10.06, 1.73 and 2.04 μM, respectively. And compound 10b had better or equivalent activity against four cell lines than Gefitinib. The activity of the compound 10b on the EGFR enzyme was subsequently tested. The Wound Healing of A549, AGS and HepG2 cells by this compound showed that the compound can inhibit the migration of cancer cells. Finally, the action channel of the compound 10b was supported by western blotting experiments. It provides useful information for the design of EGFR-TK inhibitors.
Zheng, Quan,Xu, Xuan-Bo,Jin, Hao,Zhang, Wen,Rao, Guo-Wu
(2021/10/23)

3-benzyl-6-amido-2, 4-(1H, 3H)-quinazolinedione derivatives and synthesis method and application thereof
The present invention relates to 3-Benzyl-6-Amido-2, 4-(1H,3H)-quinazolinedione derivatives and synthesis methods and application thereof, belongs to the technical field of medicine, and relates to ageneral formula (I), wherein R1, R2 and R3 are different
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Paragraph 0014; 0018; 0020; 0021

(2019/06/12)

4-AMINO-2-PYRIDO-BICYCLIC PYRIMIDINES AND USE THEREOF AS TOPOISOMERASE II INHIBITORS
The present invention concerns 4-amino-2-pyrido-bicyclic pyrimidines as type II topoisomerase inhibitors and use thereof as medicaments especially in the treatment of cancer. The invention also provides a method for the manufacture of 4- amino-2-pyrido bicyclic pyrimidines.
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(2018/07/29)

Identification of novel quinazolinedione derivatives as RORγt inverse agonist
Novel small molecules were synthesized and evaluated as retinoic acid receptor-related orphan receptor-gamma t (RORγt) inverse agonists for the treatment of inflammatory and autoimmune diseases. A hit compound, 1, was discovered by high-throughput screeni
Fukase, Yoshiyuki,Sato, Ayumu,Tomata, Yoshihide,Ochida, Atsuko,Kono, Mitsunori,Yonemori, Kazuko,Koga, Keiko,Okui, Toshitake,Yamasaki, Masashi,Fujitani, Yasushi,Nakagawa, Hideyuki,Koyama, Ryoukichi,Nakayama, Masaharu,Skene, Robert,Sang, Bi-Ching,Hoffman, Isaac,Shirai, Junya,Yamamoto, Satoshi
p. 721 - 736
(2018/02/07)

CO2 transformation under mild conditions using tripolyphosphate-grafted KCC-1-NH2
Fibrous nanosilica (KCC-1) as a catalyst support was investigated in terms of stability, recycling, and reusability. For the first time, CO2 transformation was performed via the synthesis and application of KCC-1 together with sodium tripolyphosphate (STPP) and 3-aminopropyltriethoxysilane (APTES) as its functionalized derivative. To this goal, KCC-1/STPP NPs were applied to act as a nanocatalyst with excellent catalytic activities under green reaction conditions.
Sadeghzadeh, Seyed Mohsen,Zhiani, Rahele,Moradi, Marjan
p. 535 - 544
(2018/04/26)

HETEROCYCLIC COMPOUND
The problem of the present invention is to provide a compound having a superior RORγt inhibitory action, and useful as a prophylactic or therapeutic agent for psoriasis, inflammatory bowel disease, ulcerative colitis, Crohn's disease, rheumatoid arthritis, multiple sclerosis, uveitis, asthma, ankylopoietic spondylarthritis, systemic lupus erythematosus, chronic obstructive pulmonary disease or the like. The present invention relates to a compound represented by the formula (I): [wherein each symbol is as described in the DESCRIPTION] or a salt thereof, which has an RORγt inhibitory action, and useful as a prophylactic or therapeutic agent for psoriasis, inflammatory bowel disease, ulcerative colitis, Crohn's disease, rheumatoid arthritis, multiple sclerosis, uveitis, asthma, ankylopoietic spondylarthritis, systemic lupus erythematosus, chronic obstructive pulmonary disease or the like.
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Paragraph 0461

(2017/08/01)

Coumarins and other fused bicyclic heterocycles with selective tumor-associated carbonic anhydrase isoforms inhibitory activity
Herein we report for the first time a series of 2-benzamido-N-(2-oxo-4-(methyl/trifluoromethyl)-2H-chromen-7-yl) benzamide 3a–f and substituted quinazolin-4(3H)-ones and 2H-benzo[e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxides (5, 6, 8 and 10a–c) as selective inhibitors of the tumor associated hCA IX and XII isoforms. Among the compounds reported the trifluoromethyl derivative 3d resulted the most potent against these CA isoforms with KIs of 10.9 and 6.7?nM.
Bozdag, Murat,Alafeefy, Ahmed Mahmoud,Altamimi, Abdul Malik,Vullo, Daniela,Carta, Fabrizio,Supuran, Claudiu T.
p. 677 - 683
(2016/12/27)

A 2, 4 - quinazoline dione compound preparation method
The invention belongs to the field of organic chemistry, and concretely relates to a preparation method of benzoyleneurea compounds. The preparation method comprises the following steps: a 2-aminobenzonitrile compound and carbon dioxide are used as raw materials, preferably a reaction employs acylamino divalent rare earth metal amides and DBU as catalysts at 50-150 DEG C under a normal pressure, the reaction is carried out in an aprotic polar solvent for 4-40 hours, and the benzoyleneurea compounds are obtained with a high yield. The method has the advantages of mild reaction condition, few catalyst amount, simple separation and purification, high yield and wide substrate application range.
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(2017/10/31)

Bifunctional Ionic Liquids Derived from Biorenewable Sources as Sustainable Catalysts for Fixation of Carbon Dioxide
A series of highly efficient, bifunctional ionic liquids containing a quaternary alkyl ammonium cation and an amine anion were prepared from choline and amino acids, respectively. Nine ILs were synthesized, characterized, and applied as organocatalysts for the chemical fixation of carbon dioxide to form cyclic carbonates and quinazoline-2,4(1 H,3 H)-diones. A binary mixture of an IL and a co-catalysts generates deep eutectic solvents (DESs) and accelerates the rate of the cycloaddition reaction at atmospheric pressure and low temperature (70 °C). The presence of the hydroxyl functional group of choline and the free amine group of the amino acids in the ILs has a synergistic effect on the activation of the epoxide and carbon dioxide towards the cycloaddition reactions. These ILs are biodegradable and are synthesized from easily available biorenewable sources. Additionally, this catalytic method demonstrates ultimate environmental benignity because of the mild metal- and solvent-free conditions as well as the recyclability of the catalyst and co-catalyst.
Saptal, Vitthal B.,Bhanage, Bhalchandra M.
p. 1145 - 1151
(2017/03/27)

HETEROCYCLIC COMPOUND
The present invention provides a heterocyclic compound having an RORγt inhibitory action. The present invention relates to a compound represented by the formula (I): wherein Ar is a the partial structure (1) to the partial structure (5), Q is a bivalent group selected from the group consisting of (Ia)-(If), and B is a ring optinally having substituent(s), or a salt thereof.
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Paragraph 0753

(2016/03/18)

2,4-disubstituted [...] compound, and its preparation, and pharmaceutical composition and use thereof
The invention discloses new 2,4-disubstituted quinazoline compounds and a preparation method, a medicinal composition and application thereof. The invention particularly relates to 2,4-disubstituted quinazoline compounds shown as a general formula I, medicinal salts thereof, precursors or derivatives thereof with the same biological function, a preparation method thereof, a composition containing one or more of the compounds, and application of the compounds in inhibiting activity of Pin1 enzyme, inhibiting activity of tumor growth and the like.
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Paragraph 0408-0410

(2018/02/04)

Spidery catalyst for the synthesis of quinazoline-2,4(1H,3H)-diones
In this study, a novel fibrous nanosilica (KCC-1) based nanocatalyst (Au, Pd, and Cu) with a high surface area and easy accessibility of active sites was successfully developed by a facile approach. KCC-1 with a high surface area was functionalized with multi-carboxylic hyperbranched polyglycerol groups (HPG) acting as robust anchors so that the metal nanoparticles (Au, Pd, and Cu) were well-dispersed on the fibers of the KCC-1 microspheres without aggregation. Because of the amplification effect of HPG, high loading capacities of the nanocatalysts were achieved. The synthesized KCC-1/HPG/X nanocatalyst exhibited excellent catalytic activity for the synthesis of quinazoline-2,4(1H,3H)-diones from CO2 and 2-aminobenzonitrile under mild conditions due to the easy accessibility of the active sites. High catalytic activity and ease of recovery from the reaction mixture by using filtration after several reuses without any significant loss of performance are additional eco-friendly attributes of this catalytic system.
Sadeghzadeh, Seyed Mohsen
p. 1435 - 1441
(2016/03/09)

Synthesis and Characterization of Amidato Divalent Lanthanide Complexes and Their Use in Forming 2,4-Quinazolidinones from CO2 and 2-Aminobenzonitriles
Four amidato divalent lanthanide complexes, {LnLn[N(TMS)2]THF}2 [n = 1, Ln = Eu (1); n = 2, Ln = Eu (3), Yb (4); HL1 = tBuC6H4CONHC6H3(iPr)2; HL2 = C6H5CONHC6H3(iPr)2] and {L3Eu[N(TMS)2]THF}{L32Eu(THF)2} (2) [HL3 = ClC6H4CONHC6H3(iPr)2], were synthesized and extensively characterized. This is the first time that the amidato lanthanide amides 1-4 were used to catalyze the reactions of CO2 and 2-aminobenzonitriles to form quinazoline-2,4(1H,3H)-diones at atmospheric pressure. All the complexes efficiently catalyzed the transformation, with complex 3 showing the highest activity. This catalytic system gave good to excellent yields, and good functional group tolerance. Preliminary studies were conducted to investigate the reaction mechanism.
Wang, Qianyu,Lu, Chengrong,Zhao, Bei,Yao, Yingming
p. 2555 - 2559
(2016/06/01)

Bifunctional Ionic Liquids for the Multitask Fixation of Carbon Dioxide into Valuable Chemicals
A series of task-specific ionic liquids (ILs) such as mono-, dicationic, and polymer-supported ILs were synthesized. These ILs were applied as multitasking organocatalysts for transformations of carbon dioxide into valuable chemicals through a range of reactions, including (i) cycloaddition reactions of CO2/CS2 with epoxides to form cyclic carbonates and 1,3-oxathiolane-2-thiones, (ii) transesterification of cyclic carbonates with methanol to form dimethyl carbonate, and (iii) synthesis of quinazoline-2,4(1 H,3 H)-diones and quinazoline-2,4(1 H,3 H)-dithiones from 2-aminobenzonitriles and CO2/CS2. The developed methodology is transition-metal free, solvent free, and additive free. Remarkably, the developed ILs were recyclable in up to seven consecutive cycles; thus, making this protocol green and cost effective.
Saptal, Vitthal B.,Bhanage, Bhalchandra M.
p. 244 - 250
(2016/01/26)

La-Mg mixed oxide as a highly basic water resistant catalyst for utilization of CO2 in the synthesis of quinazoline-2,4(1H,3H)-dione
The synthesis of quinazoline-2,4(1H,3H)-dione was done by direct utilization of CO2 in the cyclization of 2-aminobenzonitrile (2-ABN) using lanthanum magnesia mixed oxide (La-Mg MO) as a strong basic catalyst under mild reaction conditions in water. It gave a conversion of ～92% with 100% selectivity at 140 °C in 14 h. La-Mg MO was prepared by hydrothermal method using urea as homogeneous precipitating agent. The catalyst was characterized by different analytical techniques like BET, XRD, FT-IR, SEM, and TGA, and the basicity by CO2-TPD and acidity by NH3 TPD. Various reaction parameters were studied to predict the reaction mechanism and kinetics. The reaction follows the Langmuir-Hinshelwood-Hougen-Watson (LHHW) type kinetics model with an apparent activation energy of 23.3 kcal mol-1. The catalyst was recycled three times with an insignificant change in activity. The overall process is clean and green.
Rasal,Yadav, Ganapati D.
p. 111079 - 111089
(2016/12/03)

Carbon Dioxide Mediated Novel Synthesis of Quinazoline-2,4(1H,3H)-dione in Water
A novel, efficient, and scalable CO2 mediated synthesis of quinazoline-2,4(1H,3H)-dione was developed by a simple cyclization of 2-aminobenzonitrile with DMF in water as the solvent. This is the first report of its kind. DMF was used as the necessary carbon source in the synthesis of quinazoline-2,4(1H,3H)-dione. This synthetic protocol is very efficient; it gives >99% conversion with excellent selectivity. The product was isolated by filtration because of the highly insoluble nature of quinazoline-2,4(1H,3H)-dione in water. The co-product, dimethyl amine, also has industrial importance, and the CO2 that is used can be recycled. This protocol has wide-spread applications in the syntheses of benzimidazole and benzothiazole.
Rasal, Kalidas B.,Yadav, Ganapati D.
p. 2067 - 2073
(2016/12/24)

SMALL MOLECULE AGONISTS OF NEUROTENSIN RECEPTOR 1
Provided herein are small molecule neurotensin receptor agonists, compositions comprising the compounds, and methods of using the compounds and compositions comprising the compounds.
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Paragraph 00413

(2016/04/26)

Synthesis and antimicrobial activity of amino linked heterocycles
Amino-linked benzoxazolyl/benzothiazolyl/benzimidazolyl quinazolines were prepared and their antimicrobial activity studied. The nitro-substituted benzothiazolyl quinazoline (8f) may be a potential antibacterial agent against Staphylococcus aureus and nitro-substituted benzimidazolyl quinazoline (9f) may be a potential antifungal agent against Aspergillus niger.
Mallikarjuna Reddy, Lingaladinne,Dinneswara Reddy, Guda,Padmaja, Adivireddy,Padmavathi, Venkatapuram
p. 75 - 80
(2015/03/04)

Ionic liquid immobilized onto fibrous nano-silica: A highly active and reusable catalyst for the synthesis of quinazoline-2,4(1 H,3 H)-diones
In this study, a novel fibrous nano-silica (KCC-1) supported ionic liquid (KCC-1/IL) with high surface area and easy accessibility of active sites was successfully developed by a facile approach. The synthesized KCC-1/IL nanocatalyst exhibited excellent catalytic activity for the synthesis of quinazoline-2,4(1 H,3 H)-diones from CO2 and 2-aminobenzonitriles under mild conditions to the easy accessibility of the active sites. A high catalytic activity and ease of recovery from the reaction mixture by using filtration and several reuses without any significant loss in performance are additional eco-friendly attributes of this catalytic system.
Sadeghzadeh, Seyed Mohsen
p. 91 - 96
(2015/10/12)

Amino-functionalized carbon nanofibres as an efficient metal free catalyst for the synthesis of quinazoline-2,4(1H,3H)-diones from CO2 and 2-aminobenzonitriles
Carbon nanofibres (CNFs) functionalized with 4-amino-2,6-dimethylpyridine were found to be an efficient metal free catalyst for the synthesis of quinazoline-2,4(1H,3H)-diones from CO2 and 2-aminobenzonitriles using water as a reaction medium. The presence of water they exhibited a remarkable enhancement in reaction rates and provided high to excellent yield of the products. After completion of the reaction, the catalyst was easily separated by centrifugation and was successfully reused for several runs without showing any significant decrease in catalytic activity.
Kumar, Subodh,Verma, Sanny,Shawat, Efrat,Nessim, Gilbert Daniel,Jain, Suman L.
p. 24670 - 24674
(2015/03/30)

1-(Arylmethyl)quinazoline-2,4(1H,3H)-diones as PARP Inhibitors and the Use Thereof
Disclosed are 1-(arylmethyl)quinazoline-2,4(1H,3H)-diones thereof, represented by the Formula (I) wherein Ar, R1-R6 are defined herein. Compounds having Formula (I) are PARP inhibitors. Therefore, compounds of the invention may be us
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Page/Page column 0429

(2014/02/16)

A highly efficient way to capture CX2 (O, S) mildly in reusable ReILs at atmospheric pressure
The highly efficient transformation of CX2 (O, S) into valuable chemicals at atmospheric pressure is an attractive topic. A novel method of preparing quinazoline derivatives by capturing CX2 (O, S) in reusable, room-temperature, reversible ionic liquids (ReILs) with high yields (up to 98%) at 40 °C and atmospheric pressure was developed in this paper. The different reaction conditions were optimized and the products were easily separated from the ReILs which could be reused at least six times without considerable loss in yield. The plausible mechanism of capturing CX2 (O, S) in the ReILs was proposed and it provides a green, efficient protocol to capture CX2 (O, S) in ReILs to synthesize quinazoline derivatives. This journal is the Partner Organisations 2014.
Zheng, Hui,Cao, Xianting,Du, Kui,Xu, Jun,Zhang, Pengfei
p. 3142 - 3148
(2014/06/10)

Amine functionalized MCM-41: An efficient heterogeneous recyclable catalyst for the synthesis of quinazoline-2,4(1H,3H)-diones from carbon dioxide and 2-aminobenzonitriles in water
A simple covalently linked amine functionalized MCM-41 compound was investigated using mesoporous catalytic protocols as a highly efficient, heterogeneous and recyclable catalyst for the synthesis of a wide variety of quinazoline-2,4(1H,3H)-dione derivatives from 2-aminobenzonitriles and carbon dioxide in aqueous reaction medium. This catalytic system represents a heterogeneous and environmentally benign protocol. The effect of various reaction parameters, such as the influences of solvent, temperature, CO 2 pressure, and time for the synthesis of quinazoline-2,4(1H,3H)- diones were studied. The developed protocol can be applied for the synthesis of the most important key intermediate 6,7-dimethoxyquinazoline-2,4(1H,3H)-dione and several biologically active derivatives such as Prazosin, Bunazosin and Doxazosin. Besides this, the developed catalyst could be reused for five consecutive recycles without any significant loss in its catalytic activity. The amine functionalized MCM-41 catalyst was characterized by various characterization techniques such as FT-IR, TGA/DTA, XRD, Scanning Electron Microscopy (SEM), Transmission Electron Microscopy (TEM), and solid state 29Si CP MAS NMR analysis. This journal is the Partner Organisations 2014.
Nale, Deepak B.,Rana, Surjyakanta,Parida, Kulamani,Bhanage, Bhalchandra M.
p. 1608 - 1614
(2014/06/09)

Eco-efficient one-pot synthesis of quinazoline-2,4(1H,3H)-diones at room temperature in water
An efficient one-pot synthesis of quinazoline-2,4(1H,3H)-diones was developed. First, the reactions of anthranilic acid derivatives with potassium cyanate afforded the corresponding urea derivatives. Then, cyclization of the urea derivatives with NaOH afforded the monosodium salts of benzoylene urea. Finally, HCl treatment afforded the desired products in near-quantitative yields. This is an eco-efficient method because all the reactions were carried out in water, and the desired products were obtained simply by filtration. The aqueous filtrate was the only waste generated from the reaction. We scaled up the reaction to 1 kg starting material, thus establishing an alternative approach for the green synthesis of quinazoline-2,4(1H,3H)-diones in the chemical and pharmaceutical industries.
Tian, Xin-Chuan,Huang, Xing,Wang, Dan,Gao, Feng
p. 824 - 829
(2016/10/06)

1-(ARYLMETHYL)QUINAZOLINE-2,4(1H,3H)-DIONES AS PARP INHIBITORS AND THE USE THEREOF
Disclosed are 1-(arylmethyl)quinazoline-2,4(1H,3H)-diones thereof, represented by the Formula (I) wherein Ar, R1-R6 are defined herein. Compounds having Formula (I) are PARP inhibitors. Therefore, compounds of the invention may be us
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Page/Page column 51-52

(2012/10/18)

Is CO2 fixation promoted through the formation of DBU bicarbonate salt?
The bicyclic amidines, 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU) and 1,5-diazabicyclo[4.3.0] non-5-ene (DBN), were used for the chemical fixation of carbon dioxide. The promotion for CO2 fixation is often reported through the formation of a thermally unstable DBU or DBN bicarbonate salt. To examine the effects of the DBU or DBN bicarbonate salt, reactions of 2-aminobenzonitrile with the DBU salt or DBN salt in dimethylformamide (DMF) were performed at 20°C for 24 h in argon or carbon dioxide (0.1 MPa). However, in all the cases, 1H-quinazoline-2,4-dione was not obtained completely. In contrast with room temperature reactions, 2-aminobenzonitriles and DBU bicarbonate salt in DMF reacted for 4 h under high temperature (80°C) and CO2 atmosphere (0.1 MPa) gave 1H-quinazoline-2,4-diones in good to excellent yields. At high-temperature conditions, DBU bicarbonate salt is decomposed to DBU and carbon dioxide. Also, the carbonylation of 2-aminobenzonitrile using DBU and carbon dioxide afforded 1H-quinazoline-2,4- dione in good yields under similar reaction conditions. These results suggest that the combination of DBU or DBN as a strong base and carbon dioxide is much more important than the in situ formation of DBU or DBN bicarbonate salt for the acceleration of CO2 fixation.
Mizuno, Takumi,Nakai, Takeo,Mihara, Masatoshi
experimental part
p. 276 - 280
(2012/07/28)

Efficient [WO4]2--catalyzed chemical fixation of carbon dioxide with 2-aminobenzonitriles to quinazoline-2,4(1 H,3 H)-diones
A simple monomeric tungstate, TBA2[WO4] (I, TBA = tetra-n-butylammonium), could act as an efficient homogeneous catalyst for chemical fixation of CO2 with 2-aminobenzonitriles to quinazoline-2,4(1H,3H)-diones. Various kinds of structurally diverse 2-aminobenzonitriles could be converted into the corresponding quinazoline-2,4(1H,3H)-diones in high yields at atmospheric pressure of CO 2. Reactions of inactive 2-amino-4-chlorobenzonitrile and 2-amino-5-nitrobenzonitrile at 2 MPa of CO2 also selectively proceeded. The present system was applicable to a g-scale reaction of 2-amino-5-fluorobenzonitrile (10 mmol scale) with CO2 and 1.69 g of analytically pure quinazoline-2,4(1H,3H)-dione could be isolated. In this case, the turnover number reached up to 938 and the value was the highest among those reported for base-mediated systems so far. NMR spectroscopies showed formation of the corresponding carbamic acid through the simultaneous activation of both 2-aminobenzonitirile and CO2 by I. Kinetic and computational studies revealed that I plays an important role in conversion of the carbamic acid into the product.
Kimura, Toshihiro,Sunaba, Hanako,Kamata, Keigo,Mizuno, Noritaka
p. 13001 - 13008
(2013/02/22)

Condensation reaction of ethyl 4-oxo-4h-benzo[d][1,3]-oxazine-2- carboxylates with potassium cyanate: 2,4(1H,3H)-quinazolinediones synthesis
The condensation reaction of ethyl 4-oxo-4H-benzo[d][1,3]oxazine-2- carboxylates with acidic solution of potassium cyanate offers a novel and expedient route to the synthesis of 2,4(1H,3H)-quinazolinediones under mild reaction conditions..
Nikpour, Farzad,Havasi, Forugh,Arzegar, Zeinab
p. 2745 - 2748,4
(2020/09/16)

Synthesis and biological evaluation of novel quinazoline-derived human Pin1 inhibitors
A series of novel 2,4-disubstituted quinazoline derivatives were prepared and their inhibitory activities on hPin1 were evaluated. Of all the synthesized compounds, eight compounds displayed inhibitory activities with IC50 value at the level of 10-6 mol/L. Preliminary structure-activity relationships were analyzed in details and the binding mode of the titled compounds was predicted using FlexX algorithm. The design and optimization of novel small molecule Pin1 inhibitors will be guided by the results of this report.
Zhu, Lina,Jin, Jing,Liu, Chang,Zhang, Chongjing,Sun, Yan,Guo, Yanshen,Fu, Decai,Chen, Xiaoguang,Xu, Bailing
experimental part
p. 2797 - 2807
(2011/06/17)

QUINAZOLINONES AS PROLYL HYDROXYLASE INHIBITORS
Quinazolinone compounds of formula (I) are described, which are useful as prolyl hydroxylase inhibitors. Such compounds may be used in pharmaceutical compositions and methods for the treatment of disease states, disorders, and conditions mediated by prolyl hydroxylase activity. Thus, the compounds may be administered to treat, e.g., anemia, vascular disorders, metabolic disorders, and wound healing.
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(2011/02/18)

Non-peptidic substrate-mimetic inhibitors of Akt as potential anti-cancer agents
Akt has emerged as a critical target for the development of anti-cancer therapies. It has been found to be amplified, overexpressed, or constitutively activated in numerous human malignancies with oncogenesis derived from the simultaneous promotion of cell survival and suppression of apoptosis. A valuable alternative to the more common ATP-mimetic based chemotherapies is a substrate-mimetic approach, which has the potential advantage of inherent specificity of the substrate-binding pocket. In this paper we present the development of high affinity non-peptidic, substrate-mimetic inhibitors based on the minimum GSK3β substrate sequence. Optimization of initial peptidic leads resulted in the development of several classes of small molecule inhibitors, which have comparable potency to the initial peptidomimetics, while eliminating the remaining amino acid residues. We have identified the first non-peptidic substrate-mimetic lead inhibitors of Akt 29a-b, which have affinities of 17 and 12 μM, respectively. This strategy has potential to provide a useful set of molecular probes to assist in the validation of Akt as a potential target for anti-cancer drug design.
Kayser-Bricker, Katherine J.,Glenn, Matthew P.,Lee, Sang Hoon,Sebti, Said M.,Cheng, Jin Q.,Hamilton, Andrew D.
supporting information; experimental part
p. 1764 - 1771
(2009/09/05)

Synthesis and biological evaluation of new glutamic acid-based inhibitors of MurD ligase
Mur ligases catalyze the biosynthesis of the UDP-MurNAc-pentapeptide precursor of peptidoglycan, an essential polymer of bacterial cell-wall. They constitute attractive targets for the development of novel antibacterial agents. Here we report on the synth
Tomasic, Tihomir,Zidar, Nace,Rupnik, Veronika,Kovac, Andreja,Blanot, Didier,Gobec, Stanislav,Kikelj, Danijel,Masic, Lucija Peterlin
scheme or table
p. 153 - 157
(2009/05/07)

A new and facile synthesis of quinazoline-2,4(1 H,3H)-diones
A new and facile preparation of quinazoline-2,4(1H,3H)-diones was first reported which was the condensation of aromatic o-aminonitriles with DMF or N,N-diethylformamide in the presence of ZnCl2 (0.5-10 mol %) at 190-200 °C in the sealed reactor
Jiarong, Li,Xian, Chen,Daxin, Shi,Shuling, Ma,Qing, Li,Qi, Zhang,Jianhong, Tang
supporting information; body text
p. 1193 - 1196
(2009/08/07)

SUBSTRATE-MIMETIC AKT INHIBITOR
Disclosed herein is a species of peptide and non-peptide inhibitors of Akt, an oncogenic protein. Beginning with 0 a residue of Akt target substrate GSK-3, the functional domains of the GSK-3 residue were characterized. Functionallv homologous non-peptide groups were substituted for the amino acids of the GSK-3 creating a hybrid peptide-non-peptide and non-peptide compounds capable of binding to Akt. The non-peptide compounds show increased stability and rigidity compared to peptide counterpartsand are less susceptible to degradation. The bound non-peptide compounds exhibit an inhibitory effect on Akt, similar to peptide-based Akt inhibitors.
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Page/Page column 4-5; 10-11; 6/14

(2008/12/06)

ALICYCLIC HETEROCYCLIC COMPOUND
An alicyclic heterocyclic compound represented by the following formula or a pharmaceutically acceptable salt thereof: wherein ring A is a heterocyclic ring, ring B is a carbocyclic ring, a heterocyclic ring etc., P1 and P2 are CH or N, q and r are 0 to 2, X is -NH-, -O-, -CH2-, etc., Y is -CH2-, -CO-, -SO2-, etc., Z is -CO-, -SO2-, etc., and R3 is carbocyclic group, heterocyclic group, hydroxyl, alkoxy or amino, is useful as a controlling agent of the function of CCR4 useful for the prevention or treatment for bronchial asthma, atopic dermatitis, etc.
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Page/Page column 44

(2008/12/08)

Oxidative cyclocondensation of cyclic thio(seleno)ureas. 4. Electronic effects of the substituents and the medium
We have studied the electronic effect of substituents, steric factors, the medium, and the nature of the oxidizing agent on oxidative cyclocondensation of 2-thioxo-4-quinazolone and its substituted derivatives. We have found that electron-donor substituents promote the reaction while electronacceptor substituents inhibit the reaction. 2006 Springer Science+Business Media, Inc.
Mukarramov,Urakov,Shakhidoyatov
p. 540 - 545
(2008/02/02)

The simple solvent-free synthesis of 1H-quinazoline-2,4-diones using supercritical carbon dioxide and catalytic amount of base
Using scCO2 as a reactant and a solvent, 1H-quinazoline-2,4- diones were synthesized in good to excellent yields.
Mizuno, Takumi,Iwai, Toshiyuki,Ishino, Yoshio
p. 7073 - 7075
(2007/10/03)

Highly efficient synthesis of 1H-quinazoline-2,4-diones using carbon dioxide in the presence of catalytic amount of DBU
The first example of chemical fixation of carbon dioxide in the presence of catalytic amount of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) or DBN (1,5-diazabicyclo[4.3.0]non-5-ene) was developed. Carbon dioxide easily reacted with 2-aminobenzonitriles under
Mizuno, Takumi,Ishino, Yoshio
p. 3155 - 3158
(2007/10/03)

Tripler stability of oligodeoxynucleotides containing substituted quinazoline-2,4-(1H,3H)-dione
Triple helical structures can be observed between double-stranded nucleic acids and a third strand through the formation of Hoogsteen hydrogen bond. We report here the use of quinazoline-2,4-dione derivatives as substitutes for thymine in TA*T triplets. The synthesis and the characterization of monochloro derivatives of quinazoline-2,4-dione as well as 5-fluoro and 6-nitro substituted quinazoline rings are described. The ability of the various modified bases to promote the formation of triplexes was reached by thermal denaturation studies.
Michel, Justine,Gueguen, Genevieve,Vercauteren, Joseph,Moreau, Serge
p. 8457 - 8478
(2007/10/03)