European Journal of Chemistry 2011, 2(2), 235-237. doi:10.5155/eurjchem.2.2.235-237.205

An improved synthesis of the alkaloid Luotonin-A employing ionic liquid and water as key solvents


Taterao Marutao Potewar (1) , Muthu Kumaradoss Kathiravan (2) , Aparna Surendra Chothe (3) , Kumar Venkatram Srinivasan (4,*)

(1) Division of Organic Chemistry, National Chemical Laboratory, Pune 411008, India
(2) Department of Pharmaceutical Chemistry, Sinhagad College of Pharmacy, Pune 411041, India
(3) Department of Pharmaceutical Chemistry, All India Shri Sivaji Memorial Society’s College of Pharmacy, Pune 411001, India
(4) Division of Organic Chemistry, National Chemical Laboratory, Pune 411008, India
(*) Corresponding Author

Received: 12 Jul 2010, Accepted: 15 Dec 2010, Published: 30 Jun 2011

Abstract


Luotonin A is among the first known natural product possessing the heteroaromatic pyrroloquinazoline ring system. Although many syntheses have been reported for this compound, but they all have one or the other draw back such as a large number of steps, use of hazardous reagents like sodium hydride, low temperature reactions, and lengthy reaction time. Herein we report the synthesis of luotonin A achieved in five steps in which, two of the steps involved green solvents such as an ionic liquid and water as reaction media. In particular, we have achieved the reaction steps 1 and 3 involving the green solvents in much shorter reaction time than hitherto reported.

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Keywords


Ionic liquids; Luotonin A; Water; Pyrroloquinazoline; Volatile organic compounds; Anticancer activity

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DOI: 10.5155/eurjchem.2.2.235-237.205

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References

[1]. Hesse, M. In Alkaloids, Wiley-VCH, Weinheim, 2002, pp. 59.

[2]. Jayapaul, K.; Kavi, K. P. B.; Janardhan, R. K. In Vitro Cell Dev Boil Plant. 2005, 41, 682-685.

[3]. Xie, L. H.; Lin, J. A.; Smith, K.; Zhang, J.; Skillman, D. S. Antimicrob. Agents Chemother. 2006, 50, 1649-1655.
doi:10.1128/AAC.50.5.1649-1655.2006
PMid:16641431 PMCid:1472225

[4]. Guan, J.; Zhang, Q.; OINeil, M.; Obaldia, N.; Ager, A.; Gerena, L.; Lin, J. A. Antimicrob. Agents Chemother. 2005, 49, 4928-4933.
doi:10.1128/AAC.49.12.4928-4933.2005
PMid:16304154 PMCid:1315943

[5]. Mhaske, S. B.; Argade, N. P. Tetrahedron 2006, 62, 9787-9826.
doi:10.1016/j.tet.2006.07.098

[6]. Ma, Z.; Hano, Y.; Normura, T.; Chen, Y. Heterocycles 1997, 46, 541-546.
doi:10.3987/COM-97-S65

[7]. Thomas, C. J.; Rahier, N. J.; Hecht, S. M. Bioorg. Med. Chem. 2004, 12, 1585-1604.
doi:10.1016/j.bmc.2003.11.036

[8]. Du, W. Tetrahedron 2003, 59, 8649-8687.
doi:10.1016/S0040-4020(03)01203-1

[9]. Pizzolato, J. F.; Saltz, L. B. Lancet 2003, 361, 2235-2242.
doi:10.1016/S0140-6736(03)13780-4

[10]. Ulukan, H.; Swan, P. Drugs 2002, 62, 2039-2057.
doi:10.2165/00003495-200262140-00004
PMid:12269849

[11]. Kim, D. K.; Lee, N. Mini-Rev. Med. Chem. 2002, 2, 611-619.
doi:10.2174/1389557023405530
PMid:12370044

[12]. Lerchen, H. G. Drugs Fut. 2002, 29, 869-878.
doi:10.1358/dof.2002.027.09.694498

[13]. Zunino, F.; Dallavalle, S.; Laccabue, D.; Beretta, G.; Merlini, L.; Pratesi, G. Curr. Pharm. Design. 2002, 8, 2505-2520.
doi:10.2174/1381612023392801
PMid:12369944

[14]. Hutchinson, C. R. Tetrahedron 1981, 37, 1047-1065.
doi:10.1016/S0040-4020(01)92034-4

[15]. Hertzberg, R. P.; Caranfa, M. J.; Holden, K. G.; Jakas, D. R.; Gallagher, G.; Mattern, M. R.; Mong, S. M.; Bartus, J. O.; Johnson, R. K.; Kingsbury, W. D. J. Med. Chem. 1989, 32, 715-720.
doi:10.1021/jm00123a038
PMid:2537428

[16]. Cagir, A.; Jones, S. H.; Gao, R.; Eisenhauer, B. M.; Hecht, S. M. J. Am. Chem. Soc. 2003, 125, 13628-13629.
doi:10.1021/ja0368857
PMid:14599178

[17]. Du, W.; Curran, D. P.; Bevins, R. L.; Zimmer, S. G.; Zhang, J.; Burke, T. G. Bioorg. Med. Chem. 2002, 10, 103-110.
doi:10.1016/S0968-0896(01)00252-8

[18]. Laco, G. S.; Du, W.; Kohlhagen, G.; Sayer, J. M.; Jerina, D. M.; Burke, T. G.; Curran, D. P.; Pommier, Y. Bioorg. Med. Chem. 2004, 12, 5225-5235.
doi:10.1016/j.bmc.2004.06.046

[19]. Hautefaye, P.; Cimetiere, B.; Pierre, A.; Leonce, S.; Hickman J.; Laine, W.; Bailly, C.; Lavelle, G. Bioorg. Med. Chem. Lett. 2003, 13, 2731-2735.
doi:10.1016/S0960-894X(03)00534-1

[20]. Cagir, A.; Jones, S. H.; Eisenhauer, B. M.; Gao, R.; Hecht, S. M. Bioorg. Med. Chem. Lett. 2004, 14, 2051-2054.
doi:10.1016/j.bmcl.2004.02.069

[21]. Cagir, A.; Eisenhauer, B. M.; Gao, R.; Thomas, S. J.; Hecht, S. M. Bioorg. Med. Chem. 2004, 12, 6287-6299.
doi:10.1016/j.bmc.2004.08.052

[22]. Dallavalle, S.; Merlini, L.; Beretta, G. L.; Tinelli, S.; Zunino, F. Bioorg. Med. Chem. Lett. 2004, 14, 5757-5761.
doi:10.1016/j.bmcl.2004.09.039

[23]. Wang, H.; Ganesan, A. Tetrahedron Lett. 1998, 39, 9097-9098.
doi:10.1016/S0040-4039(98)02004-8

[24]. Kelly, T. R.; Chamberland, S.; Silva, R. A. Tetrahedron Lett. 1999, 40, 2723-2724.
doi:10.1016/S0040-4039(99)00349-4

[25]. Molina, P.; Tarranga, A.; Gonzalez-Tejero, A. Synthesis 2000, 43, 1523-1525.
doi:10.1055/s-2000-7602

[26]. Osborne, D.; Stevenson, P. J. Tetrahedron Lett. 2002, 43, 5469-5470.
doi:10.1016/S0040-4039(02)01049-3

[27]. Mhaske, S. B.; Argade, N. P. J. Org. Chem. 2004, 69, 4563-4566.
doi:10.1021/jo040153v
PMid:15202923

[28]. Twin, H.; Batey, R. A. Org. Lett. 2004, 6, 4913-4916.
doi:10.1021/ol0479848
PMid:15606098

[29]. Tangirala, R.; Antony, S.; Agama, K.; Pommier, Y.; Curran, D. P. Synlett. 2005, 18, 2843-2846.

[30]. Zhou, H. B.; Liu, G. S.; Yao, Z. J. J. Org. Chem. 2007, 725, 6270-6274.
doi:10.1021/jo070837d
PMid:17608538

[31]. Mason, J.; Bergman, J. J. Org. Biomol. Chem. 2007, 5, 2486-2490.
doi:10.1039/b707684c

[32]. Srinivas, A.; Azzouz, M.; Lopes, D.; Courillon, C.; Malacria, M. Angew Chem. Int Ed. 2007, 46, 576-579.
doi:10.1002/anie.200602940
PMid:17154202

[33]. Rahier, N. J.; Cheng, K.; Gao, R.; Eisenhauer, B. M.; Hecht, S. M. Org. Lett. 2005, 7, 835-837.
doi:10.1021/ol0400701
PMid:15727453

[34]. Cheng, K.; Rahier, N. J.; Eisenhauer, B. M.; Gao, R.; Thomas, S. J.; Hecht, S. M. J. Am. Chem. Soc. 2005, 127, 838-839.
doi:10.1021/ja0442769
PMid:15656613

[35]. Elban, M. A.; Sun, W.; Eisenhauer, B. M.; Gao, R.; Hecht, S. M. Org. Lett. 2006, 8, 3513-3516.
doi:10.1021/ol0611604
PMid:16869648

[36]. Rahier, N. J.; Eisenhauer, B. M.; Gao, R.; Thomas, S. J.; Hecht, S. M. Bioorg. Med. Chem. 2005, 13, 1381-1386.
doi:10.1016/j.bmc.2004.11.011

[37]. Lee, E. S.; Park, J. G.; Kim, S. I.; Jahng, Y. Heterocycles 2006, 68, 151-158.
doi:10.3987/COM-05-10618

[38]. Nacro, K.; Zha, C.; Guzzo, P. R.; Herr, R. J.; Peace, D.; Friedrich, T. D. Bioorg. Med. Chem. 2007, 15, 4237-4246.
doi:10.1016/j.bmc.2007.03.067

[39]. Palimkar, S. S.; Siddiqui, S. A.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. J. Org. Chem. 2003, 68, 9371-9378.
doi:10.1021/jo035153u
PMid:14629159


How to cite


Potewar, T.; Kathiravan, M.; Chothe, A.; Srinivasan, K. Eur. J. Chem. 2011, 2(2), 235-237. doi:10.5155/eurjchem.2.2.235-237.205
Potewar, T.; Kathiravan, M.; Chothe, A.; Srinivasan, K. An improved synthesis of the alkaloid Luotonin-A employing ionic liquid and water as key solvents. Eur. J. Chem. 2011, 2(2), 235-237. doi:10.5155/eurjchem.2.2.235-237.205
Potewar, T., Kathiravan, M., Chothe, A., & Srinivasan, K. (2011). An improved synthesis of the alkaloid Luotonin-A employing ionic liquid and water as key solvents. European Journal of Chemistry, 2(2), 235-237. doi:10.5155/eurjchem.2.2.235-237.205
Potewar, Taterao, Muthu Kumaradoss Kathiravan, Aparna Surendra Chothe, & Kumar Venkatram Srinivasan. "An improved synthesis of the alkaloid Luotonin-A employing ionic liquid and water as key solvents." European Journal of Chemistry [Online], 2.2 (2011): 235-237. Web. 16 Sep. 2019
Potewar, Taterao, Kathiravan, Muthu, Chothe, Aparna, AND Srinivasan, Kumar. "An improved synthesis of the alkaloid Luotonin-A employing ionic liquid and water as key solvents" European Journal of Chemistry [Online], Volume 2 Number 2 (30 June 2011)

DOI Link: https://doi.org/10.5155/eurjchem.2.2.235-237.205

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