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Pyrrolopyridines-quinazolines Inhibitors of PKR-Like ER Kinase.

ACS medicinal chemistry letters

Rosse G.
PMID: 25589923
ACS Med Chem Lett. 2014 Dec 08;6(1):21-2. doi: 10.1021/ml500482q. eCollection 2015 Jan 08.

No abstract available.

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Rosse G. Pyrrolopyridines-quinazolines Inhibitors of PKR-Like ER Kinase. ACS Med Chem Lett. 2014;6(1):21-2doi: 10.1021/ml500482q.
Rosse, G. (2015). Pyrrolopyridines-quinazolines Inhibitors of PKR-Like ER Kinase. ACS medicinal chemistry letters, 6(1), 21-2. https://doi.org/10.1021/ml500482q
Rosse, Gerard. "Pyrrolopyridines-quinazolines Inhibitors of PKR-Like ER Kinase." ACS medicinal chemistry letters vol. 6,1 (2015): 21-2. doi: https://doi.org/10.1021/ml500482q
Rosse G. Pyrrolopyridines-quinazolines Inhibitors of PKR-Like ER Kinase. ACS Med Chem Lett. 2014 Dec 08;6(1):21-2. doi: 10.1021/ml500482q. eCollection 2015 Jan 08. PMID: 25589923; PMCID: PMC4291703.
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Iron-catalyzed cascade reaction of 2-aminobenzyl alcohols with benzylamines: synthesis of quinazolines by trapping of ammonia.

Organic & biomolecular chemistry

Gopalaiah K, Saini A, Devi A.
PMID: 28660261
Org Biomol Chem. 2017 Jul 21;15(27):5781-5789. doi: 10.1039/c7ob01159h. Epub 2017 Jun 29.

A novel approach to construct 2-aryl/heteroaryl quinazolines was developed through an iron-catalyzed cascade reaction of 2-aminobenzyl alcohols with benzylamines under aerobic oxidative conditions. The reaction proceeds via the formation of N-benzylidenebenzylamines followed by oxidative trapping of ammonia/intramolecular cyclization in...

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Gopalaiah K, Saini A, Devi A. Iron-catalyzed cascade reaction of 2-aminobenzyl alcohols with benzylamines: synthesis of quinazolines by trapping of ammonia. Org Biomol Chem. 2017;15(27):5781-5789doi: 10.1039/c7ob01159h.
Gopalaiah, K., Saini, A., & Devi, A. (2017). Iron-catalyzed cascade reaction of 2-aminobenzyl alcohols with benzylamines: synthesis of quinazolines by trapping of ammonia. Organic & biomolecular chemistry, 15(27), 5781-5789. https://doi.org/10.1039/c7ob01159h
Gopalaiah, Kovuru, et al. "Iron-catalyzed cascade reaction of 2-aminobenzyl alcohols with benzylamines: synthesis of quinazolines by trapping of ammonia." Organic & biomolecular chemistry vol. 15,27 (2017): 5781-5789. doi: https://doi.org/10.1039/c7ob01159h
Gopalaiah K, Saini A, Devi A. Iron-catalyzed cascade reaction of 2-aminobenzyl alcohols with benzylamines: synthesis of quinazolines by trapping of ammonia. Org Biomol Chem. 2017 Jul 21;15(27):5781-5789. doi: 10.1039/c7ob01159h. Epub 2017 Jun 29. PMID: 28660261.
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CuI-catalyzed coupling of gem-dibromovinylanilides and sulfonamides: an efficient method for the synthesis of 2-amidoindoles and indolo[1,2-a]quinazolines.

Organic letters

Kiruthika SE, Perumal PT.
PMID: 24378141
Org Lett. 2014 Jan 17;16(2):484-7. doi: 10.1021/ol403365t. Epub 2013 Dec 30.

A Cu(I)-catalyzed, intermolecular protocol for the synthesis of 2-amidoindoles and tetrahydroindolo[1,2-a]quinazolines in shorter time and high yields is reported. The key highlight of this disclosure is the formation of 2-amidoindole and tetrahydroindolo[1,2-a]quinazoline moieties directly from gem-dibromovinylanilides and sulfonamides in...

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Kiruthika SE, Perumal PT. CuI-catalyzed coupling of gem-dibromovinylanilides and sulfonamides: an efficient method for the synthesis of 2-amidoindoles and indolo[1,2-a]quinazolines. Org Lett. 2013;16(2):484-7doi: 10.1021/ol403365t.
Kiruthika, S. E., & Perumal, P. T. (2014). CuI-catalyzed coupling of gem-dibromovinylanilides and sulfonamides: an efficient method for the synthesis of 2-amidoindoles and indolo[1,2-a]quinazolines. Organic letters, 16(2), 484-7. https://doi.org/10.1021/ol403365t
Kiruthika, Selvarangam E, and Perumal, Paramasivan Thirumalai. "CuI-catalyzed coupling of gem-dibromovinylanilides and sulfonamides: an efficient method for the synthesis of 2-amidoindoles and indolo[1,2-a]quinazolines." Organic letters vol. 16,2 (2014): 484-7. doi: https://doi.org/10.1021/ol403365t
Kiruthika SE, Perumal PT. CuI-catalyzed coupling of gem-dibromovinylanilides and sulfonamides: an efficient method for the synthesis of 2-amidoindoles and indolo[1,2-a]quinazolines. Org Lett. 2014 Jan 17;16(2):484-7. doi: 10.1021/ol403365t. Epub 2013 Dec 30. PMID: 24378141.
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I2-Catalyzed Aerobic Oxidative C(sp(3))-H Amination/C-N Cleavage of Tertiary Amine: Synthesis of Quinazolines and Quinazolinones.

The Journal of organic chemistry

Yan Y, Xu Y, Niu B, Xie H, Liu Y.
PMID: 25942678
J Org Chem. 2015 Jun 05;80(11):5581-7. doi: 10.1021/acs.joc.5b00474. Epub 2015 May 12.

An iodine-catalyzed oxidative C(sp(3))-H amination/C-N cleavage of tertiary amines couducted under an oxygen atmosphere has been developed and affords a route to quinazolines and quinazolinones in good to excellent yields via a domino ring annulation. The method is metal-free,...

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Yan Y, Xu Y, Niu B, et al. I2-Catalyzed Aerobic Oxidative C(sp(3))-H Amination/C-N Cleavage of Tertiary Amine: Synthesis of Quinazolines and Quinazolinones. J Org Chem. 2015;80(11):5581-7doi: 10.1021/acs.joc.5b00474.
Yan, Y., Xu, Y., Niu, B., Xie, H., & Liu, Y. (2015). I2-Catalyzed Aerobic Oxidative C(sp(3))-H Amination/C-N Cleavage of Tertiary Amine: Synthesis of Quinazolines and Quinazolinones. The Journal of organic chemistry, 80(11), 5581-7. https://doi.org/10.1021/acs.joc.5b00474
Yan, Yizhe, et al. "I2-Catalyzed Aerobic Oxidative C(sp(3))-H Amination/C-N Cleavage of Tertiary Amine: Synthesis of Quinazolines and Quinazolinones." The Journal of organic chemistry vol. 80,11 (2015): 5581-7. doi: https://doi.org/10.1021/acs.joc.5b00474
Yan Y, Xu Y, Niu B, Xie H, Liu Y. I2-Catalyzed Aerobic Oxidative C(sp(3))-H Amination/C-N Cleavage of Tertiary Amine: Synthesis of Quinazolines and Quinazolinones. J Org Chem. 2015 Jun 05;80(11):5581-7. doi: 10.1021/acs.joc.5b00474. Epub 2015 May 12. PMID: 25942678.
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A concise and efficient synthesis of benzimidazo[1,2-c]quinazolines through CuI-catalyzed intramolecular N-arylations.

Beilstein journal of organic chemistry

Pang X, Chen C, Li M, Xi C.
PMID: 26734086
Beilstein J Org Chem. 2015 Nov 30;11:2365-9. doi: 10.3762/bjoc.11.258. eCollection 2015.

A series of functionalized benzimidazo[1,2-c]quinazoline derivatives was obtained in excellent yields under mild conditions through a CuI-catalyzed Ullmann N-arylation starting from easily available starting materials.

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Pang X, Chen C, Li M, et al. A concise and efficient synthesis of benzimidazo[1,2-c]quinazolines through CuI-catalyzed intramolecular N-arylations. Beilstein J Org Chem. 2015;11:2365-9doi: 10.3762/bjoc.11.258.
Pang, X., Chen, C., Li, M., & Xi, C. (2015). A concise and efficient synthesis of benzimidazo[1,2-c]quinazolines through CuI-catalyzed intramolecular N-arylations. Beilstein journal of organic chemistry, 112365-9. https://doi.org/10.3762/bjoc.11.258
Pang, Xinlong, et al. "A concise and efficient synthesis of benzimidazo[1,2-c]quinazolines through CuI-catalyzed intramolecular N-arylations." Beilstein journal of organic chemistry vol. 11 (2015): 2365-9. doi: https://doi.org/10.3762/bjoc.11.258
Pang X, Chen C, Li M, Xi C. A concise and efficient synthesis of benzimidazo[1,2-c]quinazolines through CuI-catalyzed intramolecular N-arylations. Beilstein J Org Chem. 2015 Nov 30;11:2365-9. doi: 10.3762/bjoc.11.258. eCollection 2015. PMID: 26734086; PMCID: PMC4685915.
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Alkaloid constituents of Sida acuta, S. humilis, S. rhombifolia and S. spinosa.

Planta medica

Prakash A, Varma RK, Ghosal S.
PMID: 17402065
Planta Med. 1981 Dec;43(4):384-8. doi: 10.1055/s-2007-971529.

Three types of alkaloidal constituents, viz., beta-phenethylamines, quinazolines and carboxylated tryptamines, in addition to choline and betaine have been isolated from Sida acuta Burm., S. humilis Willd., S. rhombifolia L., and S. spinosa L. and characterized by their physical...

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Prakash A, Varma RK, Ghosal S. Alkaloid constituents of Sida acuta, S. humilis, S. rhombifolia and S. spinosa. Planta Med. 1981;43(4):384-8doi: 10.1055/s-2007-971529.
Prakash, A., Varma, R. K., & Ghosal, S. (1981). Alkaloid constituents of Sida acuta, S. humilis, S. rhombifolia and S. spinosa. Planta medica, 43(4), 384-8. https://doi.org/10.1055/s-2007-971529
Prakash, A, et al. "Alkaloid constituents of Sida acuta, S. humilis, S. rhombifolia and S. spinosa." Planta medica vol. 43,4 (1981): 384-8. doi: https://doi.org/10.1055/s-2007-971529
Prakash A, Varma RK, Ghosal S. Alkaloid constituents of Sida acuta, S. humilis, S. rhombifolia and S. spinosa. Planta Med. 1981 Dec;43(4):384-8. doi: 10.1055/s-2007-971529. PMID: 17402065.
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Synthesis of 3,4-benzo-7-hydroxy-2,9-diazabicyclo[3.3.1]non-7-enes by cyclization of 1,3-bis(silyl enol ethers) with quinazolines.

Organic & biomolecular chemistry

Karapetyan V, Mkrtchyan S, Schmidt A, Gütlein JP, Villinger A, Reinke H, Jiao H, Fischer C, Langer P.
PMID: 18688489
Org Biomol Chem. 2008 Aug 21;6(16):2961-8. doi: 10.1039/b803141j. Epub 2008 Jun 21.

A variety of functionalized 3,4-benzo-7-hydroxy-2,9-diazabicyclo[3.3.1]non-7-enes were prepared by one-pot cyclizations of 1,3-bis(silyl enol ethers) with quinazolines. The mechanism of the cyclization was studied by B3LYP/6-31G(d) density functional theory computations. The products could be functionalized by Suzuki cross-coupling reactions. The...

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Karapetyan V, Mkrtchyan S, Schmidt A, et al. Synthesis of 3,4-benzo-7-hydroxy-2,9-diazabicyclo[3.3.1]non-7-enes by cyclization of 1,3-bis(silyl enol ethers) with quinazolines. Org Biomol Chem. 2008;6(16):2961-8doi: 10.1039/b803141j.
Karapetyan, V., Mkrtchyan, S., Schmidt, A., Gütlein, J. P., Villinger, A., Reinke, H., Jiao, H., Fischer, C., & Langer, P. (2008). Synthesis of 3,4-benzo-7-hydroxy-2,9-diazabicyclo[3.3.1]non-7-enes by cyclization of 1,3-bis(silyl enol ethers) with quinazolines. Organic & biomolecular chemistry, 6(16), 2961-8. https://doi.org/10.1039/b803141j
Karapetyan, Vahuni, et al. "Synthesis of 3,4-benzo-7-hydroxy-2,9-diazabicyclo[3.3.1]non-7-enes by cyclization of 1,3-bis(silyl enol ethers) with quinazolines." Organic & biomolecular chemistry vol. 6,16 (2008): 2961-8. doi: https://doi.org/10.1039/b803141j
Karapetyan V, Mkrtchyan S, Schmidt A, Gütlein JP, Villinger A, Reinke H, Jiao H, Fischer C, Langer P. Synthesis of 3,4-benzo-7-hydroxy-2,9-diazabicyclo[3.3.1]non-7-enes by cyclization of 1,3-bis(silyl enol ethers) with quinazolines. Org Biomol Chem. 2008 Aug 21;6(16):2961-8. doi: 10.1039/b803141j. Epub 2008 Jun 21. PMID: 18688489.
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Synthesis and Anticancer Activity of 2-(Alkyl-, Alkaryl-, Aryl-, Hetaryl-)-[1,2,4]triazolo[1,5-c]quinazolines.

Scientia pharmaceutica

Kovalenko SI, Antypenko LM, Bilyi AK, Kholodnyak SV, Karpenko OV, Antypenko OM, Mykhaylova NS, Los TI, Kolomoets OS.
PMID: 23833709
Sci Pharm. 2013 Apr-Jun;81(2):359-91. doi: 10.3797/scipharm.1211-08. Epub 2012 Dec 23.

The combinatorial library of novel potential anticancer agents, namely, 2-(alkyl-, alkaryl-, aryl-, hetaryl-)[1,2,4]triazolo[1,5-c]quinazolines, was synthesized by the heterocyclization of the alkyl-, alkaryl-, aryl-, hetarylcarboxylic acid (3H-quinazoline-4-ylidene)hydrazides by oxidative heterocyclization of the 4-(arylidenehydrazino)quinazolines using bromine, and by the heterocyclization of...

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Kovalenko SI, Antypenko LM, Bilyi AK, et al. Synthesis and Anticancer Activity of 2-(Alkyl-, Alkaryl-, Aryl-, Hetaryl-)-[1,2,4]triazolo[1,5-c]quinazolines. Sci Pharm. 2012;81(2):359-91doi: 10.3797/scipharm.1211-08.
Kovalenko, S. I., Antypenko, L. M., Bilyi, A. K., Kholodnyak, S. V., Karpenko, O. V., Antypenko, O. M., Mykhaylova, N. S., Los, T. I., & Kolomoets, O. S. (2013). Synthesis and Anticancer Activity of 2-(Alkyl-, Alkaryl-, Aryl-, Hetaryl-)-[1,2,4]triazolo[1,5-c]quinazolines. Scientia pharmaceutica, 81(2), 359-91. https://doi.org/10.3797/scipharm.1211-08
Kovalenko, Sergiy I, et al. "Synthesis and Anticancer Activity of 2-(Alkyl-, Alkaryl-, Aryl-, Hetaryl-)-[1,2,4]triazolo[1,5-c]quinazolines." Scientia pharmaceutica vol. 81,2 (2013): 359-91. doi: https://doi.org/10.3797/scipharm.1211-08
Kovalenko SI, Antypenko LM, Bilyi AK, Kholodnyak SV, Karpenko OV, Antypenko OM, Mykhaylova NS, Los TI, Kolomoets OS. Synthesis and Anticancer Activity of 2-(Alkyl-, Alkaryl-, Aryl-, Hetaryl-)-[1,2,4]triazolo[1,5-c]quinazolines. Sci Pharm. 2013 Apr-Jun;81(2):359-91. doi: 10.3797/scipharm.1211-08. Epub 2012 Dec 23. PMID: 23833709; PMCID: PMC3700071.
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Biological effects of a new set 1,2,4-triazolo[1,5-a]quinazolines on heart rate and blood pressure.

Chemistry Central journal

Al-Salahi R, El-Tahir KE, Alswaidan I, Lolak N, Hamidaddin M, Marzouk M.
PMID: 24428932
Chem Cent J. 2014 Jan 15;8(1):3. doi: 10.1186/1752-153X-8-3.

BACKGROUND: Several quinazoline and triazole derivatives are reported to possess a wide-range of interesting pharmacological effects. Although various triazoloquinazoline subclasses having been synthesized and studied, the preparation of 1,2,4-triazolo[1,5-a]quinazolines as antihypertensive agent is still relatively unexplored. In continuation of...

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Al-Salahi R, El-Tahir KE, Alswaidan I, et al. Biological effects of a new set 1,2,4-triazolo[1,5-a]quinazolines on heart rate and blood pressure. Chem Cent J. 2014;8(1):3doi: 10.1186/1752-153X-8-3.
Al-Salahi, R., El-Tahir, K. E., Alswaidan, I., Lolak, N., Hamidaddin, M., & Marzouk, M. (2014). Biological effects of a new set 1,2,4-triazolo[1,5-a]quinazolines on heart rate and blood pressure. Chemistry Central journal, 8(1), 3. https://doi.org/10.1186/1752-153X-8-3
Al-Salahi, Rashad, et al. "Biological effects of a new set 1,2,4-triazolo[1,5-a]quinazolines on heart rate and blood pressure." Chemistry Central journal vol. 8,1 (2014): 3. doi: https://doi.org/10.1186/1752-153X-8-3
Al-Salahi R, El-Tahir KE, Alswaidan I, Lolak N, Hamidaddin M, Marzouk M. Biological effects of a new set 1,2,4-triazolo[1,5-a]quinazolines on heart rate and blood pressure. Chem Cent J. 2014 Jan 15;8(1):3. doi: 10.1186/1752-153X-8-3. PMID: 24428932; PMCID: PMC3903009.
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The oxime portmanteau motif: released heteroradicals undergo incisive EPR interrogation and deliver diverse heterocycles.

Accounts of chemical research

Walton JC.
PMID: 24654991
Acc Chem Res. 2014 Apr 15;47(4):1406-16. doi: 10.1021/ar500017f. Epub 2014 Mar 21.

Selective syntheses are now available for compounds of many classes, based on C-centered radicals, exploiting a diverse range of mechanisms. The prospect for chemistry based around N- and O-centered radicals is probably more favorable because of the importance of...

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Walton JC. The oxime portmanteau motif: released heteroradicals undergo incisive EPR interrogation and deliver diverse heterocycles. Acc Chem Res. 2014;47(4):1406-16doi: 10.1021/ar500017f.
Walton, J. C. (2014). The oxime portmanteau motif: released heteroradicals undergo incisive EPR interrogation and deliver diverse heterocycles. Accounts of chemical research, 47(4), 1406-16. https://doi.org/10.1021/ar500017f
Walton, John C. "The oxime portmanteau motif: released heteroradicals undergo incisive EPR interrogation and deliver diverse heterocycles." Accounts of chemical research vol. 47,4 (2014): 1406-16. doi: https://doi.org/10.1021/ar500017f
Walton JC. The oxime portmanteau motif: released heteroradicals undergo incisive EPR interrogation and deliver diverse heterocycles. Acc Chem Res. 2014 Apr 15;47(4):1406-16. doi: 10.1021/ar500017f. Epub 2014 Mar 21. PMID: 24654991; PMCID: PMC4012714.
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Dimerisation, rhodium complex formation and rearrangements of N-heterocyclic carbenes of indazoles.

Beilstein journal of organic chemistry

Guan Z, Namyslo JC, Drafz MH, Nieger M, Schmidt A.
PMID: 24778738
Beilstein J Org Chem. 2014 Apr 10;10:832-40. doi: 10.3762/bjoc.10.79. eCollection 2014.

Deprotonation of indazolium salts at low temperatures gives N-heterocyclic carbenes of indazoles (indazol-3-ylidenes) which can be trapped as rhodium complexes (X-ray analysis). In the absence of Rh, the indazol-3-ylidenes spontaneously dimerize under ring cleavage of one of the N,N-bonds...

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Guan Z, Namyslo JC, Drafz MH, et al. Dimerisation, rhodium complex formation and rearrangements of N-heterocyclic carbenes of indazoles. Beilstein J Org Chem. 2014;10:832-40doi: 10.3762/bjoc.10.79.
Guan, Z., Namyslo, J. C., Drafz, M. H., Nieger, M., & Schmidt, A. (2014). Dimerisation, rhodium complex formation and rearrangements of N-heterocyclic carbenes of indazoles. Beilstein journal of organic chemistry, 10832-40. https://doi.org/10.3762/bjoc.10.79
Guan, Zong, et al. "Dimerisation, rhodium complex formation and rearrangements of N-heterocyclic carbenes of indazoles." Beilstein journal of organic chemistry vol. 10 (2014): 832-40. doi: https://doi.org/10.3762/bjoc.10.79
Guan Z, Namyslo JC, Drafz MH, Nieger M, Schmidt A. Dimerisation, rhodium complex formation and rearrangements of N-heterocyclic carbenes of indazoles. Beilstein J Org Chem. 2014 Apr 10;10:832-40. doi: 10.3762/bjoc.10.79. eCollection 2014. PMID: 24778738; PMCID: PMC3999838.
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n-Bu₄NI-catalyzed selective dual amination of sp³ C-H bonds: oxidative domino synthesis of imidazo[1,5-c]quinazolines on a gram-scale.

Chemical communications (Cambridge, England)

Zhao D, Wang T, Shen Q, Li JX.
PMID: 24637953
Chem Commun (Camb). 2014 Apr 28;50(33):4302-4. doi: 10.1039/c4cc01444h.

An n-Bu4NI catalyzed domino reaction that involves selective dual amination of sp(3) C-H bonds has been developed. The protocol affords a facile and efficient approach to the synthesis of imidazo[1,5-c]quinazolines under mild conditions.

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Zhao D, Wang T, Shen Q, et al. n-Bu₄NI-catalyzed selective dual amination of sp³ C-H bonds: oxidative domino synthesis of imidazo[1,5-c]quinazolines on a gram-scale. Chem Commun (Camb). 2014;50(33):4302-4doi: 10.1039/c4cc01444h.
Zhao, D., Wang, T., Shen, Q., & Li, J. X. (2014). n-Bu₄NI-catalyzed selective dual amination of sp³ C-H bonds: oxidative domino synthesis of imidazo[1,5-c]quinazolines on a gram-scale. Chemical communications (Cambridge, England), 50(33), 4302-4. https://doi.org/10.1039/c4cc01444h
Zhao, Dan, et al. "n-Bu₄NI-catalyzed selective dual amination of sp³ C-H bonds: oxidative domino synthesis of imidazo[1,5-c]quinazolines on a gram-scale." Chemical communications (Cambridge, England) vol. 50,33 (2014): 4302-4. doi: https://doi.org/10.1039/c4cc01444h
Zhao D, Wang T, Shen Q, Li JX. n-Bu₄NI-catalyzed selective dual amination of sp³ C-H bonds: oxidative domino synthesis of imidazo[1,5-c]quinazolines on a gram-scale. Chem Commun (Camb). 2014 Apr 28;50(33):4302-4. doi: 10.1039/c4cc01444h. PMID: 24637953.
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