研究生: |
林豊鈞 Lin, Li-Chun |
---|---|
論文名稱: |
一、2-碘苯甲醯胺衍生物和炔丙基二羰基化合物以銅金屬催化進行氧化級聯雙環化反應合成3-羥基-3-呋喃基異吲哚酮衍生物
二、以一鍋化方法進行克腦文蓋爾縮合反應/亞胺化/π-Aza 電環化合成三取代吡啶
三、以銅金屬進行串連環化異吲哚並 [1,2-b] 喹唑啉-12(10H)-酮和 5,13-二氫11H-喹唑啉 [2,3-b]喹唑啉-11-酮衍生物 1.Copper Catalyzed Oxidative Cascade Double Cyclization of 2--Iodobenzamide Derivatives and Propargyl dicarbonyl Compounds for Accessing 3-Hydroxy-3-furylisoindoli¬none derivatives 2.One-Pot Three-Component Knoevenagel/Imination/6π-Azaelectrocyclization Sequence for the Synthesis of Trisubstituted Pyridines 3.Synthesis of Isoindolo [1,2-b]quinazolin-12(10H)-one and 5,13-dihydro-11H quinazolino[2,3-b]quinazolin-11-one Derivatives via Copper Catalyzed Tandem Cyclization |
指導教授: |
姚清發
Yao, Ching-Fa |
口試委員: |
葉怡均
Yeh, Yi-Chun 林文偉 Lin, Wen-Wei 劉維民 Liu, Wei-Min 柳如宗 Liu, Ju-Tsung 姚清發 Yao, Ching-Fa |
口試日期: | 2023/07/20 |
學位類別: |
博士 Doctor |
系所名稱: |
化學系 Department of Chemistry |
論文出版年: | 2023 |
畢業學年度: | 111 |
語文別: | 中文 |
論文頁數: | 218 |
中文關鍵詞: | 雜環化學 、銅金屬催化 、6π-氮雜電環化 、雙環化反應 、克腦文蓋爾縮合反應 、喹唑啉衍生物 、3-羥基 -3-呋喃基異吲哚啉酮 、串聯反應 、烏爾曼型合環反應 |
英文關鍵詞: | heterocyclic compound, Copper catalyzed, Ullmann type reaction, 6π-Azaelectrocyclization cyclization, Double cyclization, Knoevenagel-type condensation, Quinazolin derivatives, Tandem cyclization |
研究方法: | 實驗設計法 |
DOI URL: | http://doi.org/10.6345/NTNU202301328 |
論文種類: | 學術論文 |
相關次數: | 點閱:81 下載:4 |
分享至: |
查詢本校圖書館目錄 查詢臺灣博碩士論文知識加值系統 勘誤回報 |
一:利用2-碘苯甲醯胺衍生物和炔丙基二羰基化合物作為起始物並利用銅催化促成氧化級聯分子間雙環化來進行3-羥基-3-呋喃基異吲哚啉酮衍生物的一鍋化合成。本次的策略包含環化反應、偶聯反應、雙C(sp3)-H官能化。本次合成3-羥基-3-呋喃基異吲哚啉酮衍生物的策略是利用不同取代基的2-碘苯甲醯胺衍和各種不同的炔丙基二羰基及炔丙基磺醯基芳基酮。
二:我們開發出一種以溴丙烯醛、苯甲醯乙腈和乙酸銨為起始物並利用銅金屬進行催化反應歷經三個不同反應後生成三取代吡啶。3-溴丙烯醛與苯甲醯乙腈會先進行克腦文蓋爾縮合反應形成2,4-二烯酮隨後和氨進行反應,並生成相應的氮雜三烯。最後經過6π-氮雜電環化/芳構化反應並生成三取代的吡啶。
三:我們開發出一種反應過程簡單、產率高的一鍋化方法,透過銅催化將N-(2-溴芐基)-2-碘苯甲醯胺的進行串聯反應而合成出吲哚並 [1,2-b] 喹唑啉-12(10H)-酮和氰化銅
1.One-pot strategy is reported for the synthesis of 3-hydroxy-3-furylisoindolinone derivatives via copper catalyzed oxidative cascade inter-molecular double cyclisation of 2-iodobenzamide derivatives and propargyl dicarbonyl compounds in the presence of oxygen. The present strategy involves several reactions including cyclization/coupling/double C(sp3)-H functionalization in cascade manner. Wide range of 2-iodobenzamide substrates having different substituents as well as various propargyldicarbonyl and propargylsulfonyl aryl ketones are used to access variety of 3-hydroxy-3-furylisoindolinone derivatives in the present methodology.
2. A facile copper-catalyzed three-component reaction for the synthesis of trisubstituted pyridines from 3-bromopropenals, benzoylacetonitriles, and ammonium acetate (NH4OAc) is developed. The Knoevenagel-type condensation of 3-bromopropenal with benzoylacetonitrile gives 2,4-dienone with strategically placed functional groups, which reacts with in situ generated ammonia to give the corresponding azatriene. A subsequent reaction sequence of 6π-azaelectrocyclization/aromatization produces a trisubstituted pyridine under the reaction conditions.
3.Herein, we developed a simple and one pot method for the synthesis of isoindolo [1,2-b]quinazolin-12(10H)-one derivatives via copper catalyzed tandem reaction of N-(2-bromobenzyl)-2-iodobenzamide as substrate and copper cyanide. The procedure is easy, simple and the yields are good to excellent.
1. Signoretto, M.; Taghavi, S.; Ghedini, E.; Menegazzo, F., Molecules 2019, 24, 2460.
2. Timperio, A. M.; Kuiper, H. A.; Zolla, L., Xenobiotica 2003, 33.
3. Stevens, M.; Howe, C.; Ray, A.-M.; Washburn, A.; Chitre, S.; Sivinski, J.; Park, Y.; Hoang, Q. Q.; Chapman, E.; Johnson, S. M., Bioorganic & Medicinal Chemistry 2020, 28.
4. Louis M. Orr, M. D. W. R. D., M.D.; James L. Campbell, M.D, J. Am. Med. Assoc 1958, 167.
5. Recht, J.; Chansamouth, V.; White, N. J.; Ashley, E. A., Nitrofurantoin and glucose-6-phosphate dehydrogenase deficiency: a safety review. JAC Antimicrob Resist 2022, 4, dlac045.
6. Al-Badr, A. A.; Aboul-Enein, H. Y., Pilocarpine. 1983; pp 385-432.
7. Faulds, L. R. W. a. D., Drugs 1995, 49, 143-155.
8. Martin S. Wolfe, M., JAMA 1973, 224, 1601-1604.
9. James B. McAuley, B. L. H., Susan L. Stokes, John A. Becher, Jacqueline M. Roberts, Marco K. Michelson, Dennis D. Juranek, Clinical Infectious Diseases 1992, 15, 464-468.
10. Babu, N. J.; Cherukuvada, S.; Thakuria, R.; Nangia, A., Crystal Growth & Design 2010, 10, 1979-1989.
11. M. Gaab, O. E. K., J. Schupp, F. Herrmann, U. Fuhrmeister,; Pflughaupt, a. K. W., Journal of Neurology 1979, 220, 185-197.
12. Romano, D. E. H. D. M. A., Arch Intern Med. 1965, 115, 542-546.
13. Huang, X.; Dorhout Mees, E.; Vos, P.; Hamza, S.; Braam, B., Am J Physiol Renal Physiol 2016, 310, F958-71.
14. Rumpa Banerjee, K. H., Mrityunjay Banerjee, J. Rev. Life. Sci 2012, 2, 7-16.
15. Rossi, A. A. E., Tetrahedron Letters 1996, 37, 6811-6814.
16. Manna, S.; Antonchick, A. P., Org Lett 2015, 17 (17), 4300-3.
17. Antonio Arcadi, S. C., ,Sabrina Di Giuseppe, Giancarlo Fabrizi, and; Marinelli, F., Organic Letters 2002, 4, 2409-2412.
18. Bao, M.; Qian, Y.; Su, H.; Wu, B.; Qiu, L.; Hu, W.; Xu, X., Org Lett 2018, 20 (17), 5332-5335.
19. Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M., Tetrahedron 2003, 59 (25), 4661-4671.
20. S.SabriSabriFirdous, M. H. A. Z.; MauriceShamma, Phytochemistry 1987, 26 (4), 1233-1234.
21. François Chasset MD, T. T. M., Elise Cesbron MD, Annick Barbaud MD, Camille Francès MD, Laurent Arnaud MD,, Journal of the American Academy of Dermatology 2018, 78, 342-350.
22. Franks, M. E.; Macpherson, G. R.; Figg, W. D., The Lancet 2004, 363 (9423), 1802-1811.
23. Pascal, J. M., DNA Repair (Amst) 2018, 71, 177-182.
24. Houtkooper, R. H.; Canto, C.; Wanders, R. J.; Auwerx, J., Endocr Rev 2010, 31 (2), 194-223.
25. Bai, P.; Canto, C., Cell Metab 2012, 16 (3), 290-5.
26. Arumugam Suyavaran, C. R., Ramachandran Mareeswaran, Yagna Viswa Shanthi, Jayaraman Selvakumar, Selvaraj Mangalaraj, Muthuvel Suresh Kumar, Chinnasamy Ramaraj Ramanathan, Chinnasamy Thirunavukkarasu, Bioorganic & Medicinal Chemistry 2015, 23 (3), 488-498.
27. Richard M. Locksley, N. K.; Lenardo, M. J., Cell 2001, 104, 487-501.
28. Swardfager, W.; Lanctot, K.; Rothenburg, L.; Wong, A.; Cappell, J.; Herrmann, N., Biol Psychiatry 2010, 68 (10), 930-41.
29. Mehaffey, E.; Majid, D. S. A., Am J Physiol Renal Physiol 2017, 313 (4), F1005-F1008.
30. Joon Seok Park, K. U. B., Jae Voul Cho, Eun Sook Yoo, Young Seok Byun, and Myung Hwan Park Archives of Pharmacal Research volume 2001, 24, 367-370.
31. Takahiro KONDO, Y. K., Kiyoshi YOSHIDA, Yoshinobu YOSHIMURA, Biological and Pharmaceutical Bulletin 1995, 18 (2), 330-336.
32. Shi, Z.; Li, N.; Wang, W. Z.; Lu, H. K.; Yuan, Y.; Li, Z.; Ye, K. Y., Org Biomol Chem 2022, 20 (21), 4320-4323.
33. Kang, Z.; Zhang, D.; Shou, J.; Hu, W., Org Lett 2018, 20 (4), 983-986.
34. Nozawa-Kumada, K.; Matsuzawa, Y.; Ono, K.; Shigeno, M.; Kondo, Y., Chem Commun (Camb) 2021, 57 (69), 8604-8607.
35. Shen, J.; You, Q.; Fu, Q.; Kuai, C.; Huang, H.; Zhao, L.; Zhuang, Z., Org Lett 2017, 19 (19), 5170-5173.
36. Li, P.; Jia, X.; Ma, X.; Ma, W.; Sheng, Y.; Zhao, J.; Zhao, F., Asian Journal of Organic Chemistry 2019, 8 (11), 2073-2091.
37. Meşeli, T.; Doğan, Ş. D.; Gündüz, M. G.; Kökbudak, Z.; Skaro Bogojevic, S.; Noonan, T.; Vojnovic, S.; Wolber, G.; Nikodinovic-Runic, J., New Journal of Chemistry 2021, 45 (18), 8166-8177.
38. Perez, S.; Eichhorn, P.; Aga, D. S., Environ Toxicol Chem 2005, 24 (6), 1361-7.
39. Isik, M.; Akocak, S.; Lolak, N.; Taslimi, P.; Turkes, C.; Gulcin, I.; Durgun, M.; Beydemir, S., Arch Pharm (Weinheim) 2020, 353 (9), e2000102.
40. Ram, M.; Sherer, Y.; Shoenfeld, Y., J Clin Immunol 2006, 26 (4), 299-307.
41. Li, K.; Tay, F. R.; Yiu, C. K. Y., Pharmacol Ther 2020, 207, 107465.
42. Baker, A. H.; Edwards, D. R.; Murphy, G., J Cell Sci 2002, 115 (Pt 19), 3719-27.
43. Faulds, J. C. A. a. D., Drugs 1998, 55, 837-842.
44. Tribut, C. A. a. O., Drugs 2005, 65, 633-659.
45. Pogacar, Z.; Johnson, J. L.; Krenning, L.; De Conti, G.; Jochems, F.; Lieftink, C.; Velds, A.; Wardak, L.; Groot, K.; Schepers, A.; Wang, L.; Song, J. Y.; van de Ven, M.; van Tellingen, O.; Medema, R. H.; Beijersbergen, R. L.; Bernards, R.; Leite de Oliveira, R., PLoS One 2022, 17 (9), e0273182.
46. Ozawa, Y.; Kusano, K.; Owa, T.; Yokoi, A.; Asada, M.; Yoshimatsu, K., Cancer Chemother Pharmacol 2012, 69 (5), 1353-62.
47. Supuran, C. T., Expert Opinion on Investigational Drugs 2003, 12 (2), 283-287.
48. Larder, B. A.; , K. H., Stuart Bloor; , C. v. d. E.; ; Wanda DeCian, Y. W., William W. Freimuth and; Tarpley, G., AIDS 2000, 14 (13), 1943-1948.
49. Steve R. Turner, † Joseph W. Strohbach,† Ruben A. Tommasi,‡ Paul A. Aristoff,| Paul D. Johnson,|; Harvey I. Skulnick, L. A. D., † Eric P. Seest,† Paul K. Tomich,§ Michael J. Bohanon,§ Miao-Miao Horng,§; Janet C. Lynn, K.-T. C., ⊥ Roger R. Hinshaw,⊥ Keith D. Watenpaugh,† Musiri N. Janakiraman,† and; Thaisrivongs, S., J. Med. Chem 1998, 41, 3467-3476.
50. de Requena, D. G. C., Andrea; Bonora, Stefano; Ladetto, Laura; D'Avolio, Antonio; Sciandra, Mauro; Siccardi, Marco; Bargiacchi, Olivia; Sinicco, Alessandro; Di Perri, Giovanni, AIDS 2006, 20 (15), 1977-1979.
51. Chan-Tack, K. M.; Struble, K. A.; Birnkrant, D. B., AIDS Patient Care STDS 2008, 22 (11), 843-50.
52. Padmaja, R. D.; Balamurali, M. M.; Chanda, K., J Org Chem 2019, 84 (18), 11382-11390.
53. Chang, M. Y.; Wu, Y. S.; Tsai, Y. L.; Chen, H. Y., J Org Chem 2019, 84 (18), 11699-11723.
54. Curti, C.; Laget, M.; Carle, A. O.; Gellis, A.; Vanelle, P., Eur J Med Chem 2007, 42 (6), 880-4.
55. Tang, X.; Huang, L.; Xu, Y.; Yang, J.; Wu, W.; Jiang, H., Angew Chem Int Ed Engl 2014, 53 (16), 4205-8.
56. Xu, W. M.; Li, S. Z.; He, M.; Yang, S.; Li, X. Y.; Li, P., Bioorg Med Chem Lett 2013, 23 (21), 5821-4.
57. Ha, T. M.; Yao, B.; Wang, Q.; Zhu, J., Org Lett 2015, 17 (7), 1750-3.
58. Aurrecoechea, J.; Alvarez, R.; Madich, Y.; Denis, J.; Ortega, A.; Martínez, C.; Matrane, A.; Belachemi, L.; de Lera, A., Synthesis 2013, 45 (14), 2009-2017.
59. Antonio Arcadi, S. D. G., Fabio Marinelli,; Rossi, E., Adv. Synth. Catal. 2001, 343 (5).
60. Zhao, H.-Y.; Wang, Y.-c.; Cao, X.-L.; Pang, Q.-F.; Wang, H.-s.; Pan, Y.-m., RSC Advances 2017, 7 (39), 24011-24014.
61. Hsieh, Copper Catalyst for the Synthesis of Various Aryl Amido Furans and Hydroxysioindolinone 2016.
62. Hong, Z.-Y., CopperCatalyst Oxidative Cascade Inter-Molecular Double Cyclization of 2-Iodobenzamide Derivatives and Propagyl dicarbonyl/1-Phenyl-2-Tosylethanone Compound for Accessing 3-Hydroxy-3-Furylisoindilinone Derivatives. 2021.
63. Chen, Y.-F.; Wang, H.-F.; Wang, Y.; Luo, Y.-C.; Zhu, H.-L.; Xu, P.-F., Advanced Synthesis & Catalysis 2010, 352 (7), 1163-1168.
1. Ling, Y.; Hao, Z. Y.; Liang, D.; Zhang, C. L.; Liu, Y. F.; Wang, Y., The Expanding Role of Pyridine and Dihydropyridine Scaffolds in Drug Design. Drug Des Devel Ther 2021, 15, 4289-4338.
2. Gaines, K. K., UROLOGIC NURSING 2004, 24, 207-209.
3. Preynat-Seauve, O.; Nguyen, E. B.; Westermaier, Y.; Heritier, M.; Tardy, S.; Cambet, Y.; Feyeux, M.; Caillon, A.; Scapozza, L.; Krause, K. H., Front Pharmacol 2021, 12, 664608.
4. FILOTEO A. ALANO JR., M. D., GEORGE D. WEBSTER JR., M.D., F.A.C.P., Annals of Internal Medicine 1970, 72 (1), 89-91.
5. Onder, A. M.; Espinoza, V.; Berho, M. E.; Chandar, J.; Zilleruelo, G.; Abitbol, C., Pediatr Nephrol 2006, 21 (11), 1760-4.
6. Gopalachar, A. S.; Bowie, V. L.; Bharadwaj, P., Ann Pharmacother 2005, 39 (6), 1128-30.
7. Marit D. Moen, K. M., Greg L. Plosker & M. Asif A. Siddiqui, Drugs 2007, 67, 299-320.
8. Deininger, M.; Buchdunger, E.; Druker, B. J., Blood 2005, 105 (7), 2640-2653.
9. Elisabeth Buchdunger, T. O. R., Jeanette Wood, European Journal of Cancer 2002, 38, S28-S36.
10. Druker, B. J., Nat Med 2009, 15 (10), 1149-52.
11. Katherine F. Croom, S. D. a. S. J. K., Drugs 2009, 69, 1107-1140.
12. Di Giambenedetto, S.; Fabbiani, M.; Quiros Roldan, E.; Latini, A.; D'Ettorre, G.; Antinori, A.; Castagna, A.; Orofino, G.; Francisci, D.; Chinello, P.; Madeddu, G.; Grima, P.; Rusconi, S.; Di Pietro, M.; Mondi, A.; Ciccarelli, N.; Borghetti, A.; Foca, E.; Colafigli, M.; De Luca, A.; Cauda, R.; Atlas, M. S. G., J Antimicrob Chemother 2017, 72 (4), 1163-1171.
13. Diane V. Havlir, S. D. O. M., Clinical Infectious Diseases 2004, 38 (11), 1599-1604.
14. Clotilde Le Tiec, A. B., Cécile Goujard & Anne-Marie Taburet, Clinical Pharmacokinetics
2005, 44, 1035–1050.
15. Mirochnick, M.; Best, B. M.; Stek, A. M.; Capparelli, E. V.; Hu, C.; Burchett, S. K.; Rossi, S. S.; Hawkins, E.; Basar, M.; Smith, E.; Read, J. S.; Team, I. s. S., J Acquir Immune Defic Syndr 2011, 56 (5), 412-9.
16. Busti, A. J.; Hall, R. G.; Margolis, D. M., Pharmacotherapy 2004, 24 (12), 1732-47.
17. Y. Cho, V. N. N., X. Chen, D.A. Lightfoot, Andrew J. Wood Biologia Plantarum 2003, 46, 405-410.
18. Ashihara, H.; Ludwig, I. A.; Katahira, R.; Yokota, T.; Fujimura, T.; Crozier, A., Phytochemistry Reviews 2014, 14 (5), 765-798.
19. S. Casal, M. B. P. P. O., M. R. Alves, and M. A. Ferreira, J. Agric. Food Chem 2000, 48 (8), 3420-3424.
20. Taguchi, H.; Sakaguchi, M.; Shimabayashi, Y., Agricultural and Biological Chemistry 2014, 49 (12), 3467-3471.
21. Khalili, M.; Alavi, M.; Esmaeil-Jamaat, E.; Baluchnejadmojarad, T.; Roghani, M., Int Immunopharmacol 2018, 61, 355-362.
22. Zhou, J. C., L.; Zhou, S., Current Medicinal Chemistry 2012, 19, 3523-3531.
23. Gupta, R.; Parmar, M., StatPearls Publishing, Treasure Island (FL): 2022.
24. Eddleston, M.; Eyer, P.; Worek, F.; Juszczak, E.; Alder, N.; Mohamed, F.; Senarathna, L.; Hittarage, A.; Azher, S.; Jeganathan, K.; Jayamanne, S.; von Meyer, L.; Dawson, A. H.; Sheriff, M. H.; Buckley, N. A., PLoS Med 2009, 6 (6), e1000104.
25. Mahajan, G. S. A. K. W., Electroencephalography and clinical Neurophysio 1998, 107, 140-148.
26. Koichi Sakurada, K. M., Keiko Shimizu, Hiroshi Shiono,; Yasuo Seto, K. T., Mineo Yoshino, Ikuko Sakai,; Harutaka Mukoyama, a. T. T., Neurochemical Research 2003, 1401-1407.
27. Bowling, F. G., Semin Cell Dev Biol 2011, 22 (6), 611-8.
28. Dixie E. Snider, J., M.D, Tubercle 1920, 61 (4), 191-196.
29. Philippe Lheureux, A. P. a. M. G., European Journal of Emergency Medicine 2005, 12, 78-85.
30. Baxter, P., Pyridoxine-dependent and pyridoxine-responsive seizures. Dev Med Child Neurol 2001, 43 (6), 416-20.
31. McCarty, M. F., Med Hypotheses 2000, 54 (5), 803-7.
32. G. Lelord, J. P. M., C. Barthelemy, J. Martineau, and; Garreau, B., Journal of Autism and Developmental Disorders 1981, 11, 219-230.
33. S.A.Eagger, R. L., B.J.Sahakian, The Lancet 1991, 337 (8748), 989-992.
34. Ahmed, M.; Rocha, J. B.; Correa, M.; Mazzanti, C. M.; Zanin, R. F.; Morsch, A. L.; Morsch, V. M.; Schetinger, M. R., Chem Biol Interact 2006, 162 (2), 165-71.
35. Paul B. Watkins, M. H. J. Z., MD; Margaret J. Knapp, PharmD;; Stephen I. Gracon, D. K. W. L., MS, JAMA Network 1994, 271, 992-998.
36. Qizilbash N, B. J., López Arrieta J, Lewington S, Szeto S, The Cochrane Database of Systematic Reviews 2007, (3), 1-4.
37. Hantzsch, A., Chemische Berichte 1881, 14, 1637-1638.
38. Elliott, W. J.; Ram, C. V., J Clin Hypertens (Greenwich) 2011, 13 (9), 687-9.
39. Sotnik, S. O.; Subota, A. I.; Kliuchynskyi, A. Y.; Yehorov, D. V.; Lytvynenko, A. S.; Rozhenko, A. B.; Kolotilov, S. V.; Ryabukhin, S. V.; Volochnyuk, D. M., J Org Chem 2021, 86 (11), 7315-7325.
40. Zhang, Q. R.; Huang, J. R.; Zhang, W.; Dong, L., Org Lett 2014, 16 (6), 1684-7.
41. Wei, Y.; Yoshikai, N., J Am Chem Soc 2013, 135 (10), 3756-9.
42. Toyoharu Kobayashi, M. N., Toshikazu Hakogi,; Katsunori Tanaka, a. S. K., ORGANIC
LETTERS 2006, 8, 3809-3812.
43. Liu, X.; Zhang, N.; Yang, J.; Liang, Y.; Zhang, R.; Dong, D., J Org Chem 2013, 78 (7), 3323-8.
44. Kobayashi, T.; Hatano, S.; Tsuchikawa, H.; Katsumura, S., Tetrahedron Letters 2008, 49 (28), 4349-4351.
45. Şendil, K.; Keskin, S.; Balci, M., Tetrahedron 2019, 75 (46).
46. Zhou, F.; Zhang, N.; Xin, X.; Zhang, X.; Liang, Y.; Zhang, R.; Dong, D., RSC Adv. 2014, 4 (35), 18198-18204.
1. Md Zeeshan*, D. G. J., Dr. Raghvendra Bhadauria, Mr. Awadh Kishor, Sunita Purohit, International Journal of Pharmaceutical Erudition 2021, 11, 19-24.
2. Lin, S.; Li, Y.; Zheng, Y.; Luo, L.; Sun, Q.; Ge, Z.; Cheng, T.; Li, R., Eur J Med Chem 2017, 127, 442-458.
3. Bhupesh S. Samant, a. M. G. S., Medicinal Chemistry 2009, 5, 293-300.
4. D Cambridge, M. J. D., and R Massingham, British Journal of Pharmacology 1977, 59 (3), 514-515.
5. Brogden, R. N.; Heel, R. C.; Speight, T. M.; Avery, G. S., Drugs 1977, 14 (3), 163-197.
6. Green, B., J Psychiatr Pract 2014, 20 (4), 253-9.
7. Murray A. Raskind, M. D., Elaine R. Peskind, M.D., Evan D. Kanter, M.D., Eric C. Petrie, M.D., Allen Radant, M.D., Charles E. Thompson, M.D., Dorcas J. Dobie, M.D., David Hoff, PA-C, Rebekah J. Rein, J.D., Kristy Straits-Tröster, Ph.D., Ronald G. Thomas, Ph.D., and Miles M. McFall, Ph.D., American Journal of Psychiatry 2003, 160, 371-373.
8. R. S. KIRBY, S. W. C. C., M. 0. CORCORAN,C. R. CHAPPLE, M. FLANNIGAN and; MILROY, E. J. G., British Journalof Urology 1987, 60, 136-142.
9. Hub Wollersheim MD, T. T. M., Jan Fennis MD, Philip Van Eiteren PhD, Albert Van't Laar MD, Clinical Pharmacology & Therapeutics 1986, 40, 219-225.
10. W S Aronow, M. L., M Turbow, K Whittaker, S Van Camp and D Hughes, Circulation 1979, 59 (2), 344-350.
11. Taylor, H. R.; Freeman, M. K.; Cates, M. E., Am J Health Syst Pharm 2008, 65 (8), 716-22.
12. GROUP, A. S., The American Journal of Medicine 1992, 92, 69-76.
13. Oliver M.Trapp, M. K. B., Petro E. Petrides, Blood Cells, Molecules, and Diseases 1998, 24 (1), 9-13.
14. Birgegard, G.; Bjorkholm, M.; Kutti, J.; Larfars, G.; Lofvenberg, E.; Markevarn, B.; Merup, M.; Palmblad, J.; Mauritzson, N.; Westin, J.; Samuelsson, J., haematologica 2004, 89, 520-527.
15. Lawrence A. Solberg Jr, A. T., Karl J. Oles, Jerzy S. Tarach, Robert M. Petitt, Lee A. Forstrom, Murray N. Silverstein, British Journal of Haematology 1997, 99, 174-180.
16. Espasandin, Y. R.; Glembotsky, A. C.; Grodzielski, M.; Lev, P. R.; Goette, N. P.; Molinas, F. C.; Marta, R. F.; Heller, P. G., J Thromb Haemost 2015, 13 (4), 631-42.
17. MARTIN H. COHEN, G. A. W., RAJESHWARI SRIDHARA, GANG CHEN,; PAZDUR, R., The Oncologist 2003, 8, 303-306.
18. Sharma, S. V.; Bell, D. W.; Settleman, J.; Haber, D. A., Nature Reviews Cancer 2007, 7 (3), 169-181.
19. Waller, J. R. C. F., Small Molecules in Oncology 2018, 235-246.
20. Rahman, A. F.; Korashy, H. M.; Kassem, M. G., Profiles Drug Subst Excip Relat Methodol 2014, 39, 239-64.
21. SETTLEMAN, R. S. D. W. B. D. A. H., Science 2004, 305 (5687), 1163-1167.
22. Baselga, J.; Albanell, J.; Ruiz, A.; Lluch, A.; Gascon, P.; Guillem, V.; Gonzalez, S.; Sauleda, S.; Marimon, I.; Tabernero, J. M.; Koehler, M. T.; Rojo, F., J Clin Oncol 2005, 23 (23), 5323-33.
23. Hosomi, Y.; Morita, S.; Sugawara, S.; Kato, T.; Fukuhara, T.; Gemma, A.; Takahashi, K.; Fujita, Y.; Harada, T.; Minato, K.; Takamura, K.; Hagiwara, K.; Kobayashi, K.; Nukiwa, T.; Inoue, A.; North-East Japan Study, G., J Clin Oncol 2020, 38 (2), 115-123.
24. Cersosimo, R. J., Expert Opinion on Drug Safety 2006, 5 (3), 469-479.
25. J. MICHAEL VOZNIAK, P., BCOP, and JOANNA M. JACOBS, PharmD, Journal of the Advanced Practitioner in Oncology 2012, 3, 112-116.
26. Morabito, A.; Piccirillo, M. C.; Falasconi, F.; De Feo, G.; Del Giudice, A.; Bryce, J.; Di Maio, M.; De Maio, E.; Normanno, N.; Perrone, F., Oncologist 2009, 14 (4), 378-90.
27. Thornton, K.; Kim, G.; Maher, V. E.; Chattopadhyay, S.; Tang, S.; Moon, Y. J.; Song, P.; Marathe, A.; Balakrishnan, S.; Zhu, H.; Garnett, C.; Liu, Q.; Booth, B.; Gehrke, B.; Dorsam, R.; Verbois, L.; Ghosh, D.; Wilson, W.; Duan, J.; Sarker, H.; Miksinski, S. P.; Skarupa, L.; Ibrahim, A.; Justice, R.; Murgo, A.; Pazdur, R., Clin Cancer Res 2012, 18 (14), 3722-30.
28. Wells, S. A., Jr.; Gosnell, J. E.; Gagel, R. F.; Moley, J.; Pfister, D.; Sosa, J. A.; Skinner, M.; Krebs, A.; Vasselli, J.; Schlumberger, M., J Clin Oncol 2010, 28 (5), 767-72.
29. Heymach, J. V.; Paz-Ares, L.; De Braud, F.; Sebastian, M.; Stewart, D. J.; Eberhardt, W. E.; Ranade, A. A.; Cohen, G.; Trigo, J. M.; Sandler, A. B.; Bonomi, P. D.; Herbst, R. S.; Krebs, A. D.; Vasselli, J.; Johnson, B. E., J Clin Oncol 2008, 26 (33), 5407-15.
30. Herbst, R. S.; Sun, Y.; Eberhardt, W. E.; Germonpre, P.; Saijo, N.; Zhou, C.; Wang, J.; Li, L.; Kabbinavar, F.; Ichinose, Y.; Qin, S.; Zhang, L.; Biesma, B.; Heymach, J. V.; Langmuir, P.; Kennedy, S. J.; Tada, H.; Johnson, B. E., Lancet Oncol 2010, 11 (7), 619-26.
31. Martin H. Cohen, J. R. J., Yeh-Fong Chen, Rajeshwari Sridhara, Richard Pazdur, The Oncologist 2005, 10, 461-466.
32. Erlotinib in cancer treatment. Ann Oncol 2007, 18 Suppl 6, vi35-41.
33. Harari, P. C. S. H. G. V. E. A. S. V. S. A. T. A. M. C. P. M., Cancer Research 2005, 65 (8), 3328-3335.
34. Ceriani, D.; Di Giulio, A. M.; Panelli, M., Farmaco Sci 1976, 31 (5), 379-87.
35. Della Marchina, M. M.; Renzi, G.; Serofilli, S., Minerva Med 1981, 72 (3), 163-166.
36. Dr. Francesco V. Costa MD, C. B. M., Stefano Boschi PharmD, Alessandra Mussi MD, Ettore Ambrosioni MD, The Journal of Clinical Pharmacology 1990, 30 (3), 254-261.
37. TARTAGNI, F., General Pharmacology: The Vascular System 1988, 19 (1), 45-48.
38. Mondal, A.; Sahoo, M. K.; Subaramanian, M.; Balaraman, E., J Org Chem 2020, 85 (11), 7181-7191.
39. Meredeth A. McGowan, C. Z. M., and Stephen L. Buchwald*, Organic Letters 2012, 14, 3800-3803.
40. Wang, J.; Zha, S.; Chen, K.; Zhang, F.; Song, C.; Zhu, J., Org Lett 2016, 18 (9), 2062-5.
41. Huang, C.; Fu, Y.; Fu, H.; Jiang, Y.; Zhao, Y., Chem Commun (Camb) 2008, (47), 6333-5.
42. Chilin, A.; Marzaro, G.; Zanatta, S.; Barbieri, V.; Pastorini, G.; Manzini, P.; Guiotto, A., Tetrahedron 2006, 62 (52), 12351-12356.
43. Chilin, A.; Marzaro, G.; Zanatta, S.; Guiotto, A., Tetrahedron Letters 2007, 48 (18), 3229-3231.
44. Villuri, B. K.; Kotipalli, T.; kavala, V.; Ichake, S. S.; Bandi, V.; Kuo, C.-W.; Yao, C.-F., RSC Advances 2016, 6 (78), 74845-74858.
45. Kavala, V.; Yang, Z.; Konala, A.; Yang, T.-H.; Kuo, C.-W.; Ruan, J.-Y.; Yao, C.-F., European Journal of Organic Chemistry 2018, 2018 (10), 1241-1247.
46. Gawande, S. D.; Zanwar, M. R.; Kavala, V.; Kuo, C.-W.; Rajawinslin, R. R.; Yao, C.-F., Advanced Synthesis & Catalysis 2015, 357 (1), 168-176.