- Optoelectronic and charge transport properties of D-n-A type 1,3,5-triazine derivatives: A combined experimental and DFT study
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The synthesis of five D-n-A type star-shaped octupolar molecules is presented in the current work. The exploration of the potential applicability of molecules under study in organic optoelectronics as electron or hole transporting materials is carried out by DFT methods. All the molecules have a 1,3,5-triazine core, which acts as an electron acceptor (A). Phenyl ring and pyridine ring act as electron donors (D) in AZ and PZ series of molecules respectively. The donor and acceptor core are connected by -NH bridge (n). The crystal structure of a molecule in the PZ series is elucidated. Thermogravimetric studies are carried out to confirm the thermal stability of molecules. The frontier molecular orbitals of molecules are characterized with the help of cyclic voltammetry. With the assistance of DFT methodologies, the whole research presented in this work focuses on the electronic excitations, reorganization energies, electron affinity, ionization potential and features of frontier molecular orbitals of molecules. The investigation of the variation of optoelectronic properties of molecules with changing patterns of nucleophilic substitution on 1,3,5-triazine core and presence of a hetero (nitrogen) atom in the donor part of the molecule is also accomplished.
- Chetti, Prabhakar,Pola, Someshwar,V. M., Vidya
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- Heterocyclic IDH mutant inhibitor, preparation method and application thereof
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The invention discloses a heterocyclic IDH mutant inhibitor, a preparation method and application thereof, belongs to the field of medicines, and particularly relates to a s-triazine compound with structural characteristics of a general formula (I) or a pharmaceutically acceptable salt thereof, a pharmaceutical composition, a preparation method of the s-triazine compound, and application of the s-triazine compound or the pharmaceutically acceptable salt and the pharmaceutical composition as isocitrate dehydrogenase 2 (IDH2) mutant inhibitors. The compound disclosed by the invention has an obvious inhibiting effect on the activity of an IDH2 mutant (mIDH2), can effectively inhibit the process of catalyzing alpha-ketoglutaric acid to generate 2-hydroxyglutaric acid by the mIDH2, and can be used for preventing and/or treating various related diseases including cancers caused by IDH2 mutation.
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Paragraph 0364; 0370-0372
(2020/09/23)
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- Synthesis, Spectra, and Theoretical Investigations of 1,3,5-Triazines Compounds as Ultraviolet Rays Absorber Based on Time-Dependent Density Functional Calculations and three-Dimensional Quantitative Structure-Property Relationship
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A series of 1,3,5-triazines were synthesized and their UV absorption properties were tested. The computational chemistry methods were used to construct quantitative structure-property relationship (QSPR), which was used to computer aided design of new 1,3,5-triazines ultraviolet rays absorber compounds. The experimental UV absorption data are in good agreement with those predicted data using the Time-dependent density functional theory (TD-DFT) [B3LYP/6–311 + G(d,p)]. A suitable forecasting model (R > 0.8, P 0.0001) was revealed. Predictive three-dimensional quantitative structure-property relationship (3D-QSPR) model was established using multifit molecular alignment rule of Sybyl program, which conclusion is consistent with the TD-DFT calculation. The exceptional photostability mechanism of such ultraviolet rays absorber compounds was studied and confirmed as principally banked upon their ability to undergo excited-state deactivation via an ultrafast excited-state proton transfer (ESIPT). The intramolecular hydrogen bond (IMHB) of 1,3,5-triazines compounds is the basis for the excited state proton transfer, which was explored by IR spectroscopy, UV spectra, structural and energetic aspects of different conformers and frontier molecular orbitals analysis.
- Wang, Xueding,Xu, Yilian,Yang, Lu,Lu, Xiang,Zou, Hao,Yang, Weiqing,Zhang, Yuanyuan,Li, Zicheng,Ma, Menglin
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p. 707 - 723
(2018/05/05)
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- Dissociation exists in s-triazine based donor-accepter organic systems by photo-induced electron transfer
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In the organic donor-acceptor system, the dissociation of the chloride anion in the s-triazine group as the acceptor was first investigated under irradiation. Introducing the electron-deficient chromophore as acceptor 2 to the donor-acceptor module allows the photo-induced electron transfer from the s-triazine module, making the dissociation less in the donor-acceptor1-acceptor2 architecture, which has been proven to be a good strategy to increase light-stability.
- Wang, Tianyang,Sun, Haiya,Lu, Ting,Li, Fengqing,Liu, Dongzhi,Li, Wei,Zhou, Xueqin,Wang, Lichang,Wang, Tianyang,Sun, Haiya,Lu, Ting,Li, Fengqing,Hu, Wenping,Li, Wei,Zhou, Xueqin,Wang, Lichang,Bridgmohan, Chelsea N.,Wang, Lichang,Liu, Dongzhi,Li, Wei,Zhou, Xueqin,Hu, Wenping
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p. 264 - 273
(2016/12/28)
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- Cardioprotective effect of novel sulphonamides-1,3,5-triazine conjugates against ischaemic–reperfusion injury via selective inhibition of MMP-9
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Diseases affecting cardiovascular system are ranked as a top most cause of morbidity and mortality. Herein, a novel class sulphonamides-1,3,5-triazine conjugates have been synthesized and tested for inhibitory activity against MMP-2 and MMP-9. The results of the study showed that these molecules efficiently inhibit MMP-9 than MMP-2, revealing compound 8e as the most potent inhibitor (IC50?=?2.34?±?0.56?nm). Due to involvement of MMP-9 in many cardiovascular diseases, particularly in myocardial ischaemia (MI), compound 8e was further subjected for the determination of the protective effect on isoproterenol (ISO)-induced myocardial injury in rats.
- Zheng, Xiao-Zhu,Zhou, Jia-Li,Ye, Jing,Guo, Pei-Pei,Lin, Chun-Shui
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p. 756 - 765
(2016/10/19)
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- A novel triazine-aryl-bis-indole derivative inhibits both phosphodiesterase IV and expression of cell adhesion molecules
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Asthma, like many inflammation related disorders, has a complex etiology. Drugs targeting multiple pathways may prove more efficacious in these complex disorders. Cyclic 3′,5′-adenosine monophosphate (cAMP) phosphodiesterase IV (PDE IV) is one of the vali
- Banerjee, Tanima,Kar, Dipak,Krishna, Palakodety Radha,Prabhakar, Sunchu,Nomula, Rajesh,Mallula, Venkata Satyanarayana,Ravindranath, Hajari,Sridhar, Gattu,Adepu, Ramesh,Srikanth, Gourishetty,Mabalirajan, Ulaganathan,Ghosh, Balaram,Jaisankar, Parasuraman,Johri, Rakesh,Chakraborty, Dolonchapa,Mishra, Vani,Chhabra, Jasmeet Kaur,Shukla, Mamta,Paul, Bhola Nath,Bandyopadhyay, Santu,Roy, Siddhartha,Sharma, Gangavaram V. M.,Bandyopadhyay, Arun
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p. 70271 - 70281
(2015/09/15)
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- Discovery of novel 1,3,5-triazine-thiazolidine-2,4-diones as dipeptidyl peptidase-4 inhibitors with antibacterial activity targeting the S1 pocket for the treatment of type 2 diabetes
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A novel series of 1,3,5-triazine-thiazolidine-2,4-diones was synthesized and characterized by a number of analytical and spectroscopic techniques. The molecules were screened for the in vitro inhibition of dipeptidyl peptidase-4 and compound 7a showed the most prominent inhibition with IC50 = 6.25 μM. The other compounds showed considerable inhibition (IC50 = 12.11-49.21 μM). Docking studies indicated that the lipophilic thiazolidine-2,4-dione fragment of ligand 7a was oriented towards the tight lipophilic cavity of the S1 pocket of the active site formed by residues such as Tyr631, Val656, Trp659, Tyr662, Tyr666 and Val711 via the formation of H-bonds with Tyr547. One of the amines present on the wings of the triazine formed a hydrogen bond with Glu205, a vital residue for the N-terminal recognition site with an efficient CDOCKER interaction energy. In a bacterial inhibition study, the entire set of compounds showed excellent activity and, in some instances, were found to be equipotent to the cefixime used as a standard.
- Srivastava, Jitendra Kumar,Dubey, Pragya,Singh, Saumya,Bhat, Hans Raj,Kumawat, Mukesh Kumar,Singh, Udaya Pratap
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p. 14095 - 14102
(2015/02/19)
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- Experimental and quantum chemical studies of synthesized triazine derivatives as an efficient corrosion inhibitor for N80 steel in acidic medium
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Corrosion inhibition of N80 steel in a 15% HCl solution was studied using two synthesized triazine derivatives, namely: N2-(4-(2-amino-6-(4-methoxyphenyl)pyrimidine-4-yl)phenyl)-N4,N6-diphenyl-1,3,5-triazine-2,4,6-triamine
- Yadav,Kumar,Tiwari,Bahadur,Ebenso
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p. 151 - 167
(2015/10/05)
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- Synthesis, in vitro antiplasmodial activity and cytotoxicity of a series of artemisinin-triazine hybrids and hybrid-dimers
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A series of artemisinin-triazine hybrids and hybrid-dimers were synthesized and their in vitro antimalarial activity against the chloroquine sensitive (CQS), the gametocytocidal (NF54) and the choroquine resistant (CQR) Dd2 strains of Plasmodium falciparu
- Cloete, Theunis T.,De Kock, Carmen,Smith, Peter J.,N'Da, David D.
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p. 470 - 481
(2014/03/21)
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- Synthesis and structure-activity relationship study of triazine-based inhibitors of the DNA binding of NF-κB
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Nuclear transcription factor nuclear factor-kappa B (NF-κB) has diverse pathophysiological functions, and NF-κ B inhibitors are considered to be candidates for multiple therapeutic applications. We previously reported a novel triazine-based NF-κB inhibitor, 2-anilino-4,6-dichloro-1,3,5- triazine (NI241), that directly inhibits DNA binding of NF-κB. Here, we report synthesis of a series of triazine derivatives and evaluation of their structure-activity relationships for NF-κB inhibition. We found that 2-amino-4,6-dichloro-1,3,5-triazine substructure is essential for the inhibitory activity of the lead compound NI241, and modification of NI241 by introduction of an m-methoxy substituent on the phenyl ring afforded the more potent derivative 28. The structure-activity relationships identified in this study suggested a possible mechanism of irreversible NF-κB inhibition by NI241, and should be helpful in the design of other NF-κB inhibitors.
- Fujii, Shinya,Kobayashi, Takanobu,Nakatsu, Aki,Miyazawa, Hiroshi,Kagechika, Hiroyuki
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p. 700 - 708
(2014/08/05)
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- Novel deep-cavity calix[4]arene derivatives with large s-triazine conjugate systems: Synthesis and complexation for dyes
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Two novel deep-cavity calix[4]arenes 3 and 4 with large s-triazine π-conjugate systems were designed and synthesized in high yields by reacting calix[4]arene with mono phenyl-substituted cyanuric chloride or further substitution with aniline. The liquid-l
- Yang, Fafu,Liu, Weiwei,Xie, Jianwei,Bai, Xiaoyan,Guo, Hongyu
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p. 311 - 316
(2013/07/26)
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- Design, facile synthesis, antibacterial activity and structure-activity relationship of novel di- and tri-substituted 1,3,5-triazines
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Due to overwhelming generation of drug resistant microorganisms, there is an urgent need to develop novel chemotherapeutic agents. In continuation of our research on discovery of novel heterocyclic scaffolds from 1,3,5-triazine, present study deals with design and development of some novel di- and tri-substituted 1,3,5-triazine derivatives. The synthesis of title analogues were accomplished by SNAr reaction and subsequently underwent rigorous antibacterial screening against a panel of representative Gram-negative and Gram-positive bacteria. Screening results revealed that minor structural variation may induce drastic changes in activity. Whereas, amine bridge and piprazine was termed as pivotal structural fragments necessary for generation and escalation of bio-activity. The structures of newly synthesized compounds were ascertained on the basis of their analytical and spectral profiles.
- Ghosh, Surajit Kumar,Saha, Ashmita,Hazarika, Bornali,Singh, Udaya Pratap,Bhat, Hans Raj,Gahtori, Prashant
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experimental part
p. 329 - 335
(2012/05/20)
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- TRIAZINE-ARYL-BIS-INDOLES AND PROCESS FOR PREPARATION THEREOF
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A novel heterocyclic compound belonging to 'triazine-aryl-bis-indoles', useful for the treatment of asthma. The pathway by which this compound inhibits asthma is also demonstrated. The present invention also provides a process for the preparation of above
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Page/Page column 29-30
(2011/08/21)
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- Synthesis of some new S-triazine based chalcones and their derivatives as potent antimicrobial agents
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Base catalysed condensation of ketone 5 with different aldehydes give chalcones, 2.4-bis-(phenylamino)-6-[4′-{3″-(4?-substituted phenyl/2?-furanyl/2?-thienyl)-2″-propenon-1″-y l}phenylamino]-s-thriazines 6a-e. These chalcones on cyclization with hydrazine
- Solankee, Anjani,Kapadia, Kishor,Ana ?iri?,Sokovi?, Marina,Doytchinova, Irini,Geronikaki, Athina
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experimental part
p. 510 - 518
(2010/04/04)
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- Synthesis, antimalarial activity and cytotoxicity of 4-aminoquinoline-triazine conjugates
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A series of 4-aminoquinoline-triazine conjugates with different substitution pattern have been synthesized and evaluated for their in vitro antimalarial activity against chloroquine-sensitive and resistant strains of Plasmodium falciparum. Compounds 16, 19, 28 and 35 exhibited promising antimalarial activity against both strains of P. falciparum. Cytotoxicity of these compounds was tested against three cell lines. Several compounds did not show any cytotoxicity up to a high concentration (48 μM), others exhibited mild toxicities but selective index for antimalarial activity was high for most of these conjugates.
- Manohar, Sunny,Khan, Shabana I.,Rawat, Diwan S.
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scheme or table
p. 322 - 325
(2010/04/02)
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- Discovery of new 1,3,5-triazine scaffolds with potent activityagainst Mycobacterium tuberculosis H37Rv
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A series of eighty one 2,4,6-trisubstituted-1,3,5-triazines were synthesized and evaluated in vitro for the growth inhibition of Mycobacterium tuberculosis H37Rv. Fifteen compounds from this series exhibited good to moderate activity with an MIC in the ra
- Sunduru, Naresh,Gupta, Leena,Chaturvedi, Vinita,Dwivedi, Richa,Sinha, Sudhir,Chauhan, Prem M.S.
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experimental part
p. 3335 - 3345
(2010/08/06)
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- Synthesis and characterization of s-triazine based 1,5-benzothiazepines and isoxazoles
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Series of compounds 2,4-bis-phenylamino-6-[4′-{2″-(substituted phenyl/cinnamyl/2?-furanyl/2?-thicnyl)-2″, 3″-dihydro-1″,5″-benzothiazepine-4″-yl}phenyl amino]-s-triazine 7(a-f) were prepared by reaction of different chalcones and 2-amino thiophenol in the
- Solankee, Anjani
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scheme or table
p. 993 - 997
(2011/04/26)
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- Synthesis and antibacterial evaluation of s-triazine based chalcones and their derivatives
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Various 2-(phenylamino/4′-substituted phenylamino)-4-(phenylainino/ 4′-substituted phenylamino)-6-[4′-{3″-(4?-{2′- (5′-ethylpyridin-2′-yl)-ethoxy}-phenyl)-2″-propenon-1″- yl}-phenylamino]-s-triazine 6(a-e) were prepared by reaction of different ketones 5(
- Solankee, Anjani,Kapadia, Kishor,Solankee, Sejal,Patel, Ghanshyam
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scheme or table
p. 837 - 840
(2010/06/15)
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- An efficient, "green" approach to aryl amination of cyanuric chloride using acetic acid as solvent
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(Chemical Equation Presented) Acetic acid is an inexpensive and environmentally friendly solvent for facile, clean and high-yielding aryl amination of cyanuric chloride with aromatic amines, including nitroanilines. Aryl animation in acetic acid medium and isolation protocol are greatly simplified as compared to previously reported procedures. Under proper conditions, it is possible to attach the same or different aniline residues in a controlled way to obtain in excellent yields symmetrical and unsymmetrical 1,3,5-triazine derivatives, respectively.
- Kolmakov, Kirill A.
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p. 533 - 539
(2008/09/18)
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- Simple and efficient synthetic routes to bioactive s-triazinyl dithiocarbamate derivatives
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Series of 2,4-diarylamino-6-[N-(3′-methylphenyl)dithiocarbamoyl]-s- triazines (4a-l) and 2,4-bis[N-(3′-methylphenyl)dithiocarbamoyl]-6- arylamino-s-triazines (7a-l) were synthesized by two different synthetic routes. In the first route (A), 2,4,6-tricholoro-s-triazine (1) was condensed with N-(3-methylphenyl)ammoniumdithiocarbamate to afford compounds 3 or 6, which on reaction with different aryl amines afforded compounds 4a-l or 7a-l. In the second route (B), condensation of 1 with different aryl amines yielded compounds 2a-l or 5a-l. On further treatment with N-(3-methylphenyl) ammoniumdithiocarbamate these afforded compounds 4a-l or 7a-l. The newly synthesized compounds 4a-l and 7a-l were characterized by elemental analyses, infrared (IR), and 1H nuclear magnetic resonance (NMR) spectroscopic investigation. All the products were evaluated for their antibacterial and antifungal activity.
- Desai,Dodiya,Trivedi,Shah
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p. 495 - 506
(2008/12/23)
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- Synthesis and characterization of some novel isoxazoles and 1,5-benzothiazepines bearing 5-triazine nucleus
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The title compounds 7a-d and 8a-d have been prepared starting from chalcones 6a-d having i-triazine nucleus. These chalcones 6a-d on cyclisation with hydroxylamine hydrochloride in presence of alkali and 2-aminothiophenol in presence of a few drops of gla
- Solankee, Anjani,Kapadia, Kishor,Solankee, Pankit,Prajapati, Yogesh,Patel, Hiral,Solankee, Sejal
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p. 473 - 476
(2008/09/20)
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- Synthesis and bioevaluation of hybrid 4-aminoquinoline triazines as a new class of antimalarial agents
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The emergence and rapid spread of chloroquine resistant strains of Plasmodium falciparum has dramatically reduced the chemotherapeutic options. Towards this goal, a series of new class of hybrid 4-aminoquinoline triazines were synthesized and screened aga
- Kumar, Ashok,Srivastava, Kumkum,Raja Kumar,Puri,Chauhan, Prem M.S.
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scheme or table
p. 6530 - 6533
(2009/09/06)
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- Reactions of aniline in acetic acid solutions containing cyanuric chloride and hydrogen chloride acceptors
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Two reaction pathways in acetic acid solution containing cyanuric chloride, aniline, and some hydrogen chloride acceptors (triethylamine, sodium acetate, pyridine) were studied. Both aryl animation and acylation can be performed with high yields under proper reaction conditions. Contrary to the only known literature report on the reactions between carbonic acids and cyanuric chloride in. the presence of a hydrogen chloride acceptor (triethylamine), it was established that acid chlorides are not formed. A scheme involving the replacement of chlorine atoms by acetate ion in the initial stage was proposed for the acylation of aniline promoted by cyanuric chloride.
- Kolmakov, Kirill A.
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p. 1070 - 1074
(2008/09/17)
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- Synthesis and antitumor evaluation of a novel series of triaminotriazine derivatives
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A series of triaminotriazine derivatives (compounds 5a-f, 6a-x, and 7a-g) was designed, synthesized, and evaluated for their inhibition activities to colorectal cancer (CRC) cell lines (HCT-116 and HT-29). Most of the synthesized compounds demonstrated moderate anti-proliferatory effects on both HCT-116 and HT-29 cell lines at the concentration of 10 μM. The inhibitory activities against HCT-116 and HT-29 cell lines were discussed to develop the structure-activity relationships of this new series. Compounds 6l and 6o exhibited prominent inhibition activities toward HCT-116, with IC50s of 0.76 and 0.92 μM, respectively. The in vivo antitumor studies and pharmacokinetics of compound 6l showed that it might be a promising new hit for further development of antitumor agents.
- Zheng, Mingfang,Xu, Chenghui,Ma, Jianwei,Sun, Yan,Du, Feifei,Liu, Hong,Lin, Liping,Li, Chuan,Ding, Jian,Chen, Kaixian,Jiang, Hualiang
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p. 1815 - 1827
(2008/02/03)
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- Synthesis and studies of some novel s-triazine based aminopyrimidines, isoxazoles and 1,5-benzothiazepines
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An elegant synthesis of the titled compounds 7a-e, 8a-e and 9a-e have been presented starting from chalcones 6a-e based on s-triazine nucleus. These chalcones 6a-e on cyclisation with guanidine nitrate and hydroxylamine hydrochloride in the presence of al
- Solankee, Anjani,Kapadia, Kishor,Solankee, Pankit,Prajapati, Yogesh,Patel, Hiral,Solankee, Sejal
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p. 1707 - 1712
(2008/09/19)
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- Triaminotriazine DNA helicase inhibitors with antibacterial activity
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Screening of a chemical library in a DNA helicase assay involving the Pseudomonas aeruginosa DnaB helicase provided a triaminotriazine inhibitor with good antibacterial activity but associated cytotoxicity toward mammalian cells. Synthesis of analogs provided a few inhibitors that retained antibacterial activity and demonstrated a significant reduction in cytotoxicity. The impact of serum and initial investigations toward a mode of action highlight several features of this class of compounds as antibacterials.
- McKay, Geoffrey A.,Reddy, Ranga,Arhin, Francis,Belley, Adam,Lehoux, Dario,Moeck, Greg,Sarmiento, Ingrid,Parr, Thomas R.,Gros, Philippe,Pelletier, Jerry,Far, Adel Rafai
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p. 1286 - 1290
(2007/10/03)
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- LPAAT-B inhibitors and uses thereof
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The invention relates to triazines and the use thereof to inhibit lysophosphatidic acid acyltransferase β (LPAAT-β) activity. The invention further relates to methods of treating cancer using said triazines. The invention also relates to methods for scree
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- New varieties of crystalline architecture produced by small changes in molecular structure in tape complexes of melamines and barbiturates
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This paper describes the crystal structures of a series of seven 1:1 complexes between N,N′-bis(m-X-phenyl)-melamine and 5,5-diethylbarbituric acid (X = H, F, Cl, Br, I, CH3, and CF3). This series provides small perturbations on the
- Zerkowski, Jonathan A.,Mathias, John P.,Whitesides, George M.
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p. 4305 - 4315
(2007/10/02)
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