Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
REVIEW

Recent Developments on Ultrasound-Assisted Synthesis of Bioactive N-Heterocycles at Ambient Temperature*

Bubun Banerjee
+ Author Affiliations
- Author Affiliations

Department of Chemistry, Indus International University, Village and Post Office Bathu, District Una, Himachal Pradesh-174301, India. Email: banerjeebubun@gmail.com




Bubun Banerjee was born in Mamudpur, Burdwan, West Bengal, India, in 1987. He received his B.Sc. degree in chemistry from St Xavier’s College, Kolkata, under the authority of the University of Calcutta in 2008 and obtained his M.Sc. degree specializing in organic chemistry from the University of Delhi in 2010. After successfully completing the UGC-CSIR NET Examination in 2010, he went on to do his Ph.D. under the supervision of Professor (Dr) Goutam Brahmachari at the Visva-Bharati University, Santiniketan, West Bengal, India. Presently he is working as an assistant professor of chemistry in the Department of Chemistry, Indus International University, Bathu, Una, Himachal Pradesh, India. His research interests are focused on the development of novel synthetic methodologies for biologically relevant compounds with special emphasis on greener aspects.

Australian Journal of Chemistry 70(8) 872-888 https://doi.org/10.1071/CH17080
Submitted: 8 February 2017  Accepted: 13 March 2017   Published: 12 April 2017

Abstract

N-Heterocycles represent privileged structural subunits well distributed in naturally occurring compounds with immense biological activities. The last decade has seen a tremendous practice to carry out reactions at ambient temperature avoiding harsh reaction conditions. By applying ultrasonic radiation in organic synthesis we can make synthetic protocols more sustainable and can carry out reactions at room temperature avoiding the traditional thermal harsh reaction conditions. Therefore the synthesis of biologically relevant N-heterocycles at room temperature under the influence of ultrasonic irradiation is one of the advancing areas in the 21st century among organic chemists. The present review summarises the latest developments on ultrasound-assisted synthesis of biologically relevant N-heterocycles at ambient temperature.


References

[1]  G. Brahmachari, Handbook of Pharmaceutical Natural Products 2010 (Wiley-VCH: Weinheim).

[2]  G. V. S. Kumar, Y. Rajendraprasad, B. P. Mallikarjuna, S. M. Chandrashekar, C. Kistayya, Eur. J. Med. Chem. 2010, 45, 2063.
         | CrossRef |

[3]  S. A. Al-Issa, Saudi Pharm. J. 2013, 21, 305.
         | CrossRef | 1:STN:280:DC%2BC3sbht1Ghtg%3D%3D&md5=f7a6afdb5bbfd9ee92294856fb3a10c7CAS |

[4]  T. E.-S. Ali, Eur. J. Med. Chem. 2009, 44, 4539.
         | CrossRef | 1:CAS:528:DC%2BD1MXht1GgtbrL&md5=f43487ecfbb79a59ebb6d47235502858CAS |

[5]  F. Janssens, J. Torremans, M. Janssen, R. A. Stokbroekx, M. Luyckx, P. A. Janssen, J. Med. Chem. 1985, 28, 1925.
         | CrossRef | 1:CAS:528:DyaL2MXlvFKjsb0%3D&md5=d360be58c841356d42c39d5a17b194adCAS |

[6]  J. J. Baldwin, E. L. Engelhardt, R. Hirschmann, G. S. Ponticello, J. G. Atkinson, B. K. Wasson, C. S. Sweet, A. Scriabine, J. Med. Chem. 1980, 23, 65.
         | CrossRef | 1:CAS:528:DyaL3cXltFOiug%3D%3D&md5=54dac0a909f7df2441b75e023b23da6aCAS |

[7]  H. Matsuoka, N. Ohi, M. Mihara, H. Suzuki, K. Miyamoto, N. Maruyama, K. Tsuji, N. Kato, T. Akimoto, Y. Takeda, K. Yano, T. Kuroki, J. Med. Chem. 1997, 40, 105.
         | CrossRef | 1:CAS:528:DyaK28XntlWrtb8%3D&md5=d399eeee40799c8b86e040f4308e4fafCAS |

[8]  R. Vinodkumar, S. D. Vaidya, B. V. S. Kumar, U. N. Bhise, S. B. Bhirud, U. C. Mashelkar, Eur. J. Med. Chem. 2008, 43, 986.
         | CrossRef | 1:CAS:528:DC%2BD1cXlslKmu7o%3D&md5=c4c56ff5b258f4ec86292468503bc17bCAS |

[9]  A. R. Chabukswar, B. S. Kuchekar, S. C. Jagdale, P. D. Lokhande, V. V. Chabukswar, S. U. Shisodia, R. H. Mahabal, A. M. Londhe, N. S. Ojha, Arabian J. Chem. 2016, 9, 704.
         | CrossRef | 1:CAS:528:DC%2BC2cXitVertr%2FM&md5=90f33a12de289b50650f79174d8e99bdCAS |

[10]  D. D. Gaikwad, A. D. Chapolikar, C. G. Devkate, K. D. Warad, A. P. Tayade, R. P. Pawar, A. J. Domb, Eur. J. Med. Chem. 2015, 90, 707.
         | CrossRef | 1:CAS:528:DC%2BC2cXitVWhsLjM&md5=0b5cf9e7a4b7c34e120a9fada9d86988CAS |

[11]  S. Kitchener, P. Nasveld, M. D. Edstein, Am. J. Trop. Med. Hyg. 2007, 76, 494.
         | 1:CAS:528:DC%2BD2sXkt12lsLo%3D&md5=d517c18e140f48d3bec4d262f2552c92CAS |

[12]  H. S. Abd-Ellah, M. Abdel-Aziz, M. E. Shoman, E. A. M. Beshr, T. S. Kaoud, A. S. F. F. Ahmed, Bioorg. Chem. 2016, 69, 48.
         | CrossRef | 1:CAS:528:DC%2BC28XhsFKlsrbI&md5=97e93b3c5497efa10e0df299230f5ac8CAS |

[13]  X. Yu, P. Wei, Z. Wang, Y. Liu, L. Wang, Q. Wang, Pest Manag. Sci. 2016, 72, 371.
         | CrossRef | 1:CAS:528:DC%2BC2MXntVWrs7g%3D&md5=2da7413b6b3859ec5805a81b0e3f04a9CAS |

[14]  Z. Wang, P. Wei, L. Wang, Q. Wang, J. Agric. Food Chem. 2012, 60, 10212.
         | CrossRef | 1:CAS:528:DC%2BC38XhsVGisrvI&md5=a90bf9bbebecd999933cd3f073aaab87CAS |

[15]  B. Su, C. Cai, M. Deng, D. Liang, L. Wang, Q. Wang, Bioorg. Med. Chem. Lett. 2014, 24, 2881.
         | CrossRef | 1:CAS:528:DC%2BC2cXotFGgurk%3D&md5=8cb598fd51b03faa3c10d2c17c02e289CAS |

[16]  J. L. Hinkle, K. H. Cheever, Brunner & Suddarth’s Textbook of Medical-Surgical Nursing (13th edn) 2014 (Wolters Kluwer Health/Lippincott Williams & Wilkins: Philadelphia, PA).

[17]  B. Banerjee, G. Brahmachari, J. Chem. Res. 2014, 38, 745.
         | CrossRef | 1:CAS:528:DC%2BC2MXisFansbw%3D&md5=326b8d1730a12e2af98c5c51f78071deCAS |

[18]  W. Brandt, L. Mologni, L. Preu, T. Lemcke, C. Gambacorti-Passerini, C. Kunick, Eur. J. Med. Chem. 2010, 45, 2919.
         | CrossRef | 1:CAS:528:DC%2BC3cXmtF2js74%3D&md5=2f62253283a3e4498ba34629a7d31e3eCAS |

[19]  N. M. Evdokimov, A. S. Kireev, A. A. Yakovenko, M. Y. Antipin, I. V. Magedova, A. Kornienko, Tetrahedron Lett. 2006, 47, 9309.
         | CrossRef | 1:CAS:528:DC%2BD28Xht1KktbjE&md5=19592a0b371daceaa9acf91966b3f59aCAS |

[20]  S. Mitra, A. K. Bagdi, A. Majee, A. Hajra, Tetrahedron Lett. 2013, 54, 4982.
         | CrossRef | 1:CAS:528:DC%2BC3sXhtFOhsbzJ&md5=fb52a821180cfde2a0464aef91407c32CAS |

[21]  W. C. Neuhaus, G. Moura-Letts, Tetrahedron Lett. 2016, 57, 4974.
         | CrossRef | 1:CAS:528:DC%2BC28Xhs1CltLvI&md5=66523fc5485dda9aee56522bb61ff275CAS |

[22]  J. M. Khurana, A. Chaudhary, A. Lumb, B. Nand, Green Chem. 2012, 14, 2321.
         | CrossRef | 1:CAS:528:DC%2BC38XhtVOmsr3K&md5=cad379b5b709ea8faa938f92b3d2d134CAS |

[23]  A. K. Verma, D. Choudhary, R. K. Saunthwal, V. Rustagi, M. Patel, R. K. Tiwari, J. Org. Chem. 2013, 78, 6657.
         | CrossRef | 1:CAS:528:DC%2BC3sXptFGquro%3D&md5=97c98b05091b90483112da88dfc1d603CAS |

[24]  G. Brahmachari, Room Temperature Organic Synthesis 2015 (Elsevier: Amsterdam).

[25]  G. Brahmachari, S. Das, Tetrahedron Lett. 2012, 53, 1479.
         | CrossRef | 1:CAS:528:DC%2BC38XhvVGlu7g%3D&md5=6edccb270ba24a19c97c3793ebf9efbcCAS |

[26]  G. Maiti, U. Kayal, R. Karmakar, R. N. Bhattacharya, Tetrahedron Lett. 2012, 53, 1460.
         | CrossRef | 1:CAS:528:DC%2BC38XhvVGms78%3D&md5=79ebe1f48a4b7e27c18c379c96f39c40CAS |

[27]  G. Brahmachari, B. Banerjee, Asian J. Org. Chem. 2016, 5, 271.
         | CrossRef | 1:CAS:528:DC%2BC28Xns1ahtQ%3D%3D&md5=ef6e1b42b08fbcb274e70db172bb0e29CAS |

[28]  C. Mukhopadhyay, P. K. Tapaswia, R. J. Butcher, Tetrahedron Lett. 2010, 51, 1797.
         | CrossRef | 1:CAS:528:DC%2BC3cXisFKktbw%3D&md5=18156c81f44c4c638bda2064b5aa1fe1CAS |

[29]  T. J. Mason, Chem. Soc. Rev. 1997, 26, 443.
         | CrossRef | 1:CAS:528:DyaK1cXjsV2gsg%3D%3D&md5=9c7bad5817fadaff2736a15b02a805dbCAS |

[30]  B. Banerjee, Ultrason. Sonochem. 2017, 35, 1.
         | CrossRef | 1:CAS:528:DC%2BC28XhslWis7rM&md5=1b04abf5e2132924f0be9f94edc0819cCAS |

[31]  R. W. Brimblecombe, W. A. M. Duncan, G. J. Durant, J. C. Emmett, C. R. Ganellin, M. E. Parons, J. Int. Med. Res. 1975, 3, 86.
         | CrossRef | 1:CAS:528:DyaE2MXltVygsbY%3D&md5=702015d53b1819561c81fd454be8748fCAS |

[32]  Y. Tanigawara, N. Aoyama, T. Kita, K. Shirakawa, F. Komada, M. Kasuga, K. Okumura, Clin. Pharmacol. Ther. 1999, 66, 528.
         | CrossRef | 1:CAS:528:DyaK1MXotVCjt7c%3D&md5=a52befe140320e4d9924aaf976feb460CAS |

[33]  W. Hunkeler, H. Mohler, L. Pieri, P. Polc, E. P. Bonetti, R. Cumin, R. Schaffner, W. Haefely, Nature 1981, 290, 514.
         | CrossRef | 1:CAS:528:DyaL3MXlvVSlurc%3D&md5=fa87672dc521dd1b70f7e1fe547ce4a4CAS |

[34]  S. L. Abrahams, R. J. Hazen, A. G. Batson, A. P. Phillips, J. Pharmacol. Exp. Ther. 1989, 249, 359.
         | 1:CAS:528:DyaL1MXktlegtLw%3D&md5=ab44fd24d1e49a9f4870bff78585781fCAS |

[35]  G. V. M. Sharma, Y. Jyothi, P. S. Lakshmi, Synth. Commun. 2006, 36, 2991.
         | CrossRef | 1:CAS:528:DC%2BD28XhtF2rtrfK&md5=1dcbe870a71cdf1ab24369856e9af4e7CAS |

[36]  M. M. Heravi, K. Bakhtiari, H. A. Oskooie, S. Taheri, J. Mol. Catal. Chem. 2007, 263, 279.
         | CrossRef | 1:CAS:528:DC%2BD2sXhtlWhtbg%3D&md5=c30da30ddf099dcd7984627a9c83dee0CAS |

[37]  S. A. Siddiqui, U. C. Narkhede, S. S. Palimkar, T. Daniel, R. J. Lahoti, K. V. Srinivasan, Tetrahedron 2005, 61, 3539.
         | CrossRef | 1:CAS:528:DC%2BD2MXit1yku7s%3D&md5=e0cf978f785736de853f98c65c855226CAS |

[38]  A. Shaabani, A. Rahmati, B. Aghaaliakbari, J. Safaei-Ghomi, Synth. Commun. 2006, 36, 65.
         | CrossRef | 1:CAS:528:DC%2BD28Xksleqtg%3D%3D&md5=f0b2b860d2e57cca561032cba3426fc7CAS |

[39]  M. Kidwai, P. Mothsra, V. Bansal, R. Goyal, Monatsh. Chem. 2006, 137, 1189.
         | CrossRef | 1:CAS:528:DC%2BD28XptlOns7Y%3D&md5=aa9760718a3a114f4c8b0aed1e9c7f44CAS |

[40]  J. N. Sangshetti, N. D. Kokare, S. A. Kothakar, D. B. Shinde, Monatsh. Chem. 2008, 139, 125.
         | CrossRef | 1:CAS:528:DC%2BD1cXht1Knsrs%3D&md5=56f92734687c4be60d6288072baee4caCAS |

[41]  A. Y. Usyatinsky, Y. L. Khmelnitsky, Tetrahedron Lett. 2000, 41, 5031.
         | CrossRef | 1:CAS:528:DC%2BD3cXkslWnu7Y%3D&md5=837e5e4ce81b5056a60b1a34e488c1b7CAS |

[42]  S. E. Wolkenberg, D. D. Winoski, W. H. Leister, Y. Wang, Z. Zhao, C. W. Lindsley, Org. Lett. 2004, 6, 1453.
         | CrossRef | 1:CAS:528:DC%2BD2cXisFaqtL8%3D&md5=835c0279245acb9d8e042d35c2b10508CAS |

[43]  L. M. Wang, Y. H. Wang, H. Tian, Y. F. Yao, J. H. Shao, B. Liu, J. Fluor. Chem. 2006, 127, 1570.
         | CrossRef | 1:CAS:528:DC%2BD28Xht1CmurrO&md5=0e386d143da464ca8888685e7d15422dCAS |

[44]  K. F. Shelke, S. Sapkal, S. Sonal, B. R. Madje, B. B. Shingate, M. S. Shingare, Bull. Korean Chem. Soc. 2009, 30, 1057.
         | CrossRef | 1:CAS:528:DC%2BD1MXntFGntLk%3D&md5=acb0f6f02560cb7ef97ac2a43c569519CAS |

[45]  S. Damavandi, J. Chem. Pharm. Res. 2011, 3, 1157.
         | 1:CAS:528:DC%2BC38XhslKnur8%3D&md5=7320aa81dcc2f13285080d15abcd40f1CAS |

[46]  R. A. Jones, Pyrroles: Part II 1992 (Wiley: New York, NY).

[47]  B. Eftekhari-Sis, S. Vahdati-Khajeh, Current Chem. Lett. 2013, 2, 85.
         | CrossRef | 1:CAS:528:DC%2BC3sXltlKgtr8%3D&md5=781aee8a6c6b0813fcd9a68c471bd8a6CAS |

[48]  L. E. Seitz, W. J. Suling, R. C. Reynolds, J. Med. Chem. 2002, 45, 5604.
         | CrossRef | 1:CAS:528:DC%2BD38XosVCgur8%3D&md5=82e70f2e942f821fc8a04defbe1e4886CAS |

[49]  J. A. Pereira, A. M. Pessoa, M. N. D. S. Cordeiroc, R. Fernandes, C. Prudêncio, J. P. Noronhaf, M. Vieira, Eur. J. Med. Chem. 2015, 97, 664.
         | CrossRef | 1:CAS:528:DC%2BC2cXhtFWnurrN&md5=98860ce1bdd9838b08765edd9efe512dCAS |

[50]  O. O. Ajani, Eur. J. Med. Chem. 2014, 85, 688.
         | CrossRef | 1:CAS:528:DC%2BC2cXhtleiur3N&md5=ec1457c662d6fba4026f585737a4398eCAS |

[51]  S. T. Hazeldine, L. Polin, J. Kushner, J. Paluch, K. White, M. Edelstein, E. Palomino, T. H. Corbett, J. P. Horwitz, J. Med. Chem. 2001, 44, 1758.
         | CrossRef | 1:CAS:528:DC%2BD3MXjtVWisr4%3D&md5=b78b57adc7322b2aaa410019d0b08bbdCAS |

[52]  S. A. Raw, C. D. Wilfred, R. J. Taylor, Org. Biomol. Chem. 2004, 2, 788.
         | CrossRef | 1:CAS:528:DC%2BD2cXhsFCjtr0%3D&md5=fe664ada5d515566281d42961fbdd617CAS |

[53]  C. Venkatesh, B. Singh, P. K. Mahata, H. IIa, H. Junjappa, Org. Lett. 2005, 7, 2169.
         | CrossRef | 1:CAS:528:DC%2BD2MXjvVSlurk%3D&md5=dad40bca3e6e450a4bea17e6053d5dbbCAS |

[54]  R. S. Bhosale, S. R. Sarda, S. S. Ardhapure, W. N. Jadhav, S. R. Bhusare, R. P. Pawar, Tetrahedron Lett. 2005, 46, 7183.
         | CrossRef | 1:CAS:528:DC%2BD2MXhtVSru7bP&md5=f3eecae6c141dee4a6feaa48c4a53674CAS |

[55]  S. V. More, M. N. V. Sastry, C. C. Wang, C. F. Yao, Tetrahedron Lett. 2005, 46, 6345.
         | CrossRef | 1:CAS:528:DC%2BD2MXns1SgsL0%3D&md5=4b069e8d5d84bc7f6702f1b0bfef939dCAS |

[56]  S. V. More, M. N. V. Sastry, C. F. Yao, Green Chem. 2006, 8, 91.
         | CrossRef | 1:CAS:528:DC%2BD28XhsF2gug%3D%3D&md5=783cec4fe3f94be391d70023a0faff26CAS |

[57]  M. M. Heravi, S. Taheri, K. Bakhtiari, H. A. Oskooie, Catal. Commun. 2007, 8, 211.
         | CrossRef | 1:CAS:528:DC%2BD2sXivFemsA%3D%3D&md5=944d5b22a047510fe9321459526dfa96CAS |

[58]  M. M. Heravi, M. H. Tehrani, K. Bakhtiari, H. A. Oskooie, Catal. Commun. 2007, 8, 1341.
         | CrossRef | 1:CAS:528:DC%2BD2sXotVCns7s%3D&md5=809dbef0561670a6186ee70918cbc8adCAS |

[59]  A. Kumar, S. Kumar, A. Saxena, A. De, S. Mozumdar, Catal. Commun. 2008, 9, 778.
         | CrossRef | 1:CAS:528:DC%2BD1cXhvFyiu7s%3D&md5=f3d67de8513d64845ce0391a99e57346CAS |

[60]  S. Ahmad, M. Ali, Chin. J. Chem. 2007, 25, 818.
         | CrossRef | 1:CAS:528:DC%2BD2sXnvVWht7s%3D&md5=fbac14a49698728dd5c05e6245185af4CAS |

[61]  H. R. Darabi, F. Tahoori, K. Aghapoor, F. Taala, F. Mohsenzadeh, J. Braz. Chem. Soc. 2008, 19, 1646.
         | CrossRef | 1:CAS:528:DC%2BD1cXhsV2mtbfN&md5=1e56034b86e29f62045185836079e6f6CAS |

[62]  W.-X. Guo, H.-L. Jin, J.-X. Chen, F. Chen, J.-C. Ding, H.-Y. Wu, J. Braz. Chem. Soc. 2009, 20, 1674.
         | CrossRef | 1:CAS:528:DC%2BC3cXnsVeq&md5=248d9be911080554d1543db029ed376eCAS |

[63]  J.-T. Li, Z.-P. Lin, J.-F. Han, T.-S. Li, Synth. Commun. 2004, 34, 2623.
         | CrossRef | 1:CAS:528:DC%2BD2cXlslCmtLc%3D&md5=ff2d0a157bef44effdd993986df05d17CAS |

[64]  S. Kumar, S. Bawa, H. Gupta, Mini Rev. Med. Chem. 2009, 9, 1648.
         | CrossRef | 1:CAS:528:DC%2BC3cXmtVygtL4%3D&md5=a1e8a72836786e5c679ec8bc8b42402aCAS |

[65]  V. R. Solomon, H. Lee, Curr. Med. Chem. 2011, 18, 1488.
         | CrossRef | 1:CAS:528:DC%2BC3MXpslOit70%3D&md5=0bf5519159fe93a50877f903d9d9f283CAS |

[66]  M. O. Puskullu, B. Tekiner, S. Suzen, Mini Rev. Med. Chem. 2013, 13, 365.
         | 1:CAS:528:DC%2BC3sXksVGqu7s%3D&md5=3c8abb7ff9a23fdcd26a91b448e831c2CAS |

[67]  H. Shinkai, T. Ito, T. Iida, Y. Kitao, H. Yamada, I. Uchida, J. Med. Chem. 2000, 43, 4667.
         | CrossRef | 1:CAS:528:DC%2BD3cXnvVKhsb0%3D&md5=6d9de9e0997f97b6edfdf0875dc72477CAS |

[68]  D. Azarifar, D. Sheikh, Acta Chim. Slov. 2012, 59, 664.
         | 1:CAS:528:DC%2BC38XhsFKms77K&md5=0b8d5e3ad5f154eb65fa1279ea6674a5CAS |

[69]  D. Azarifar, D. Sheikh, Synth. Commun. 2013, 43, 2517.
         | CrossRef | 1:CAS:528:DC%2BC3sXkvFOrtbs%3D&md5=bef70ce7cfc095c19e9628b60cd557b6CAS |

[70]  J. Yang, Q. Li, J. Zhang, W. Lin, J. Wang, Y. Wang, Z. Huang, D. Shi, Molecules 2013, 18, 14519.
         | CrossRef |

[71]  C. O. Kappe, Tetrahedron 1993, 49, 6937.
         | CrossRef | 1:CAS:528:DyaK2cXnslWrtA%3D%3D&md5=5f14caecf5f009c9e696afa4ef1f6661CAS |

[72]  A. Shaabani, A. H. Rezayan, A. Rahmati, M. Sharifi, Monatsh. Chem. 2006, 137, 77.
         | CrossRef | 1:CAS:528:DC%2BD2MXhtlCqu7zF&md5=27a6fdaaea40a6427d5583aefe971527CAS |

[73]  S.-X. Wang, Z.-Y. Li, J.-C. Zhang, J.-T. Li, Ultrason. Sonochem. 2008, 15, 677.
         | CrossRef | 1:CAS:528:DC%2BD1cXks1eis7s%3D&md5=4499501b4383ed0eff3d7443ada23b8fCAS |

[74]  P. Biginelli, P. Gazz, Chim. Ital. 1893, 23, 360.

[75]  J.-T. Li, J.-F. Han, J.-H. Yang, T.-S. Li, Ultrason. Sonochem. 2003, 10, 119.
         | CrossRef | 1:CAS:528:DC%2BD3sXjt1Khur0%3D&md5=765c5f07ff0f43f185dafd1ac64410d3CAS |

[76]  A. R. Gholap, K. Venkatesan, T. Daniel, R. J. Lahoti, K. V. Srinivasan, Green Chem. 2004, 6, 147.
         | CrossRef | 1:CAS:528:DC%2BD2cXhslGis7w%3D&md5=c61bf415c5ebbc56920311acca2c98daCAS |

[77]  H. Kumar, A. Parmar, Ultrason. Sonochem. 2008, 15, 129.
         | CrossRef | 1:CAS:528:DC%2BD2sXht1GhtLbM&md5=8de27cec222750e1610f65e31077a950CAS |

[78]  P. G. Mandhane, R. S. Joshi, D. R. Nagargoje, C. H. Gill, Tetrahedron Lett. 2010, 51, 3138.
         | CrossRef | 1:CAS:528:DC%2BC3cXlvVOns7k%3D&md5=32c086d4274b668236dc046acb6213d9CAS |

[79]  A. N. Dadhania, V. K. Patel, D. K. Raval, J. Braz. Chem. Soc. 2011, 22, 511.
         | CrossRef | 1:CAS:528:DC%2BC3MXkslantLY%3D&md5=42eb1d40b5f8c02ce856616ee1f6a6efCAS |

[80]  A. Siddekha, S. H. S. Azzam, M. A. Pasha, Synth. Commun. 2014, 44, 424.
         | CrossRef | 1:CAS:528:DC%2BC3sXhvVaiu7jM&md5=b63fff10d915e83c532ac27c438389b8CAS |

[81]  B.-H. Chen, J.-T. Li, G.-F. Chen, Ultrason. Sonochem. 2015, 23, 59.
         | CrossRef |

[82]  D. R. Bristow, I. L. Martin, J. Neurochem. 1990, 54, 751.
         | CrossRef | 1:CAS:528:DyaK3cXhtlaqtbg%3D&md5=8cb01cafd695671acc5a1978895f3d7bCAS |

[83]  J. Zezula, A. Slany, W. Sieghart, Eur. J. Pharmacol. 1996, 301, 207.
         | CrossRef | 1:CAS:528:DyaK28XjtFejsr4%3D&md5=6331d7a2eafa856973c01065b3fb5f3bCAS |

[84]  J. B. Patel, J. B. Malick, Eur. J. Pharmacol. 1982, 78, 323.
         | CrossRef | 1:CAS:528:DyaL38XhvFehurs%3D&md5=56d2bf6e0c1defe5654bffaccaacb090CAS |

[85]  S. A. Thompson, P. B. Wingrove, L. Connelly, P. J. Whiting, K. A. Wafford, Mol. Pharmacol. 2002, 61, 861.
         | CrossRef | 1:CAS:528:DC%2BD38Xis1Ogu70%3D&md5=1ab1fb8212df334bbe9763a81b466d0fCAS |

[86]  A. Dandia, S. L. Gupta, V. Parewa, RSC Adv. 2014, 4, 6908.
         | CrossRef | 1:CAS:528:DC%2BC2cXotVKisg%3D%3D&md5=f178cb4008a5fab98eab26c0971b22b3CAS |

[87]  E. S. Gladkov, K. A. Gura, S. M. Sirko, S. M. Desenko, U. Groth, V. A. Chebanov, Beilstein J. Org. Chem. 2012, 8, 2100.
         | CrossRef | 1:CAS:528:DC%2BC38XhvVyisb7K&md5=9c94e09a53e7a94a12a68a0db78fee92CAS |

[88]  J. Liu, M. Lei, L. Hu, Green Chem. 2012, 14, 840.
         | CrossRef | 1:CAS:528:DC%2BC38XjtFyms7k%3D&md5=9403cb0e2f4cd99f57c9a55b98764ecbCAS |

[89]  V. Alagarsamy, V. R. Solomon, M. Murugan, Bioorg. Med. Chem. 2007, 15, 4009.
         | CrossRef | 1:CAS:528:DC%2BD2sXkvFOisrs%3D&md5=2911c40c66c43e300f15f87adbd7ff8bCAS |

[90]  S. M. Sondhi, S. Rajvanshi, M. Johar, N. Bharti, A. Azam, A. K. Singh, Eur. J. Med. Chem. 2002, 37, 835.
         | CrossRef | 1:CAS:528:DC%2BD38Xosl2itLc%3D&md5=366a07c1068d337fe4291ee6dc893b1dCAS |

[91]  C. G. Neochoritis, T. Zarganes-Tzitzikas, C. A. Tsoleridis, J. Stephanidou-Stephanatou, C. A. Kontogiorgis, D. J. Hadjipavlou-Litina, T. Choli Papadopoulou, Eur. J. Med. Chem. 2011, 46, 297.
         | CrossRef | 1:CAS:528:DC%2BC3cXhsFyltL3M&md5=0eddecd283c9a5c15e90b4c471475f9fCAS |

[92]  L.-H. Chen, T.-W. Chung, B. D. Narhe, C.-M. Sun, ACS Comb. Sci. 2016, 18, 162.
         | CrossRef | 1:CAS:528:DC%2BC28XisVSjsrw%3D&md5=6c4f89fd92f50911d125ddd0dde40663CAS |

[93]  S. Boutaleb-Charki, C. Marín, C. R. Maldonado, M. J. Rosales, J. Urbano, R. Guitierrez-Sánchez, M. Quirós, J. M. Salas, M. Sánchez-Moreno, Drug Metab. Lett. 2009, 3, 35.
         | CrossRef | 1:CAS:528:DC%2BD1MXkvVSgsbY%3D&md5=29791bf51aad0d70aeb5fe8adeda7711CAS |

[94]  G. Ruisi, L. Canfora, G. Bruno, A. Rotondo, T. F. Mastropietro, E. A. Debbia, M. A. Girasolo, B. Megna, J. Organomet. Chem. 2010, 695, 546.
         | CrossRef | 1:CAS:528:DC%2BC3cXhtlClt7o%3D&md5=bd288aaf78916d08536256021d52ae89CAS |

[95]  M. M. A. El-Gendy, M. Shaaban, K. A. Shaaban, A. M. El-Bondkly, H. Laatsch, J. Antibiot 2008, 61, 149.
         | CrossRef | 1:CAS:528:DC%2BD1cXkvVyqurk%3D&md5=9574f64773ac75beea6489691ff6f8beCAS |

[96]  K. Ablajan, W. Kamil, A. Tuoheti, S. Wan-Fu, Molecules 2012, 17, 1860.
         | CrossRef | 1:CAS:528:DC%2BC38Xjtlagurc%3D&md5=6932db1b16ffa8626fe306f84345eb5eCAS |

[97]  M. A. Abou-Gharbia, P. H. Doukas, Heterocycles 1979, 12, 637.
         | CrossRef | 1:CAS:528:DyaE1MXktl2hs78%3D&md5=f50fe6696aa48af6edab8ffcac986f72CAS |

[98]  M. J. Kornet, A. P. Thio, J. Med. Chem. 1976, 19, 892.
         | CrossRef | 1:CAS:528:DyaE28XksVSltr8%3D&md5=2323306aa99b6f73a5a0137abe4e4990CAS |

[99]  S. J. T. Rezaei, M. R. Nabid, A. Yari, S. W. Ng, Ultrason. Sonochem. 2011, 18, 49.
         | CrossRef |

[100]  S.-Q. Ge, Y.-Y. Hua, M. Xia, Ultrason. Sonochem. 2009, 16, 232.
         | CrossRef | 1:CAS:528:DC%2BD1cXhtlSms7jJ&md5=8a62ea94366b51a859829a67fc4c0732CAS |

[101]  H. Chen, S.-Y. Wang, X.-P. Xu, S.-J. Ji, Synth. Commun. 2011, 41, 3280.
         | CrossRef | 1:CAS:528:DC%2BC38XhtFWqs7o%3D&md5=2411531dc64558aa6fced426b1ae4a69CAS |

[102]  Y. Zou, Y. Hu, H. Liu, D. Shi, ACS Comb. Sci. 2012, 14, 38.
         | CrossRef | 1:CAS:528:DC%2BC3MXhsFKkt7%2FP&md5=a821bba37f03da8d203f73ac6df71386CAS |

[103]  J. Wang, X. Bai, C. Xu, Y. Wang, W. Lin, Y. Zou, D. Shi, Molecules 2012, 17, 8674.
         | CrossRef | 1:CAS:528:DC%2BC38XhtFams7rO&md5=5621402b1e13aa711457593898d04d91CAS |

[104]  A. M. A. Al-Kadasi, G. M. Nazeruddin, J. Chem. Pharm. Res. 2013, 5, 204.
         | 1:CAS:528:DC%2BC3sXhsVegu7zN&md5=95c137dad0009f015bae76b2fda55475CAS |

[105]  N. Mulakayala, D. Rambabu, M. R. Raja, M. Chaitanya, C. S. Kumar, A. M. Kalle, G. R. Krishna, C. M. Reddy, M. V. B. Rao, M. Pal, Bioorg. Med. Chem. 2012, 20, 759.
         | CrossRef | 1:CAS:528:DC%2BC38XpsFSntw%3D%3D&md5=187e9d9a4a093699fb35c4799fce2ffaCAS |

[106]  A. Ramazani, M. Rouhani, F. Z. Nasrabadi, F. Gouranlou, Phosphorus Sulfur Silicon Relat. Elem. 2015, 190, 20.
         | CrossRef | 1:CAS:528:DC%2BC2cXitValurnO&md5=ce4139dcd6d3d04b37e967ee0134182dCAS |

[107]  P. Conti, M. D. Amici, G. Grazioso, G. Roda, A. Pinto, K. B. Hansen, B. Nielsen, U. Madsen, H. Bräuner-Osborne, J. Egebjerg, V. Vestri, D. E. Pellegrini-Giampietro, P. Sibille, F. C. Acher, C. D. Micheli, J. Med. Chem. 2005, 48, 6315.
         | CrossRef | 1:CAS:528:DC%2BD2MXpvFaiur0%3D&md5=888a746066041a76474655d11fec17c6CAS |

[108]  S. Srivastava, L. K. Bajpai, S. Batra, A. P. Bhaduri, J. P. Maikhuri, G. Gupta, J. D. Dhar, Bioorg. Med. Chem. 1999, 7, 2607.
         | CrossRef | 1:CAS:528:DC%2BD3cXpsVGh&md5=5dfbb61bf74a3d53bb44e935ce86a503CAS |

[109]  M. Barcelo, E. Ravina, C. F. Masaguer, E. Dominguez, F. M. Areias, J. Brea, M. Loza, Bioorg. Med. Chem. Lett. 2007, 17, 4873.
         | CrossRef | 1:CAS:528:DC%2BD2sXos1ant70%3D&md5=8f6485be12f2c45f179af027770fb8dcCAS |

[110]  G. J. Hatheway, C. Hansch, K. H. Kim, S. R. Milstein, C. L. Schmidt, R. N. Smith, F. R. Quinn, J. Med. Chem. 1978, 21, 563.
         | CrossRef | 1:CAS:528:DyaE1cXkvF2lurs%3D&md5=85a68e44cadfa9e712de4242cd6a4a4eCAS |

[111]  E.-S. A. M. Badawey, I. M. El-Ashmawey, Eur. J. Med. Chem. 1998, 33, 349.
         | CrossRef | 1:CAS:528:DyaK1cXjvFKqtLY%3D&md5=7800b8b6cae60a205ef30c6640df4941CAS |

[112]  D. M. Bailey, P. E. Hansen, A. G. Hlavac, E. R. Baizman, J. Pearl, A. F. Defelice, M. E. Feigenson, J. Med. Chem. 1985, 28, 256.
         | CrossRef | 1:CAS:528:DyaL2MXhtFegtLs%3D&md5=7f0cacf69fe69579162ee6f336d44876CAS |

[113]  Z.-B. Huang, L.-L. Li, Y.-W. Zhao, H.-Y. Wang, D.-Q. Shi, J. Heterocycl. Chem. 2014, 51, E309.
         | CrossRef | 1:CAS:528:DC%2BC2cXhsVGhurjN&md5=0120b5d1fb852e0c15ab374746910d57CAS |

[114]  A. Dandia, A. K. Jain, D. S. Bhati, Synth. Commun. 2011, 41, 2905.
         | CrossRef | 1:CAS:528:DC%2BC3MXovF2htr8%3D&md5=bad5dd30aba4d5c1484ad5fa09418da7CAS |

[115]  A. Dandia, R. Singh, J. Joshi, S. Maheshwari, P. Soni, RSC Adv. 2013, 3, 18992.
         | CrossRef | 1:CAS:528:DC%2BC3sXhsFegtr7E&md5=fc99a08bd886a3ef92a71646f42d0f6aCAS |

[116]  A. Dandia, R. Singh, S. Bhaskaran, S. D. Samant, Green Chem. 2011, 13, 1852.
         | CrossRef | 1:CAS:528:DC%2BC3MXotlynt78%3D&md5=280114b3ee6015294b9ba170b67da1d8CAS |

[117]  K. Arya, D. S. Rawat, H. Sasai, Green Chem. 2012, 14, 1956.
         | CrossRef | 1:CAS:528:DC%2BC38XptVGqtLc%3D&md5=312b726e17a8d64db78141e2d4d9bd4dCAS |

[118]  W. T. Sing, C. L. Lee, S. L. Yeo, S. P. Lim, M. M. Sim, Bioorg. Med. Chem. Lett. 2001, 11, 91.
         | CrossRef | 1:CAS:528:DC%2BD3MXotlKntw%3D%3D&md5=400213660c71f801d8f3116c6e8dd9d7CAS |

[119]  E. B. Grant, D. Guiadeen, E. Z. Baum, B. D. Foleno, H. Jin, D. A. Montenegro, E. A. Nelson, K. Bush, D. J. Hlasta, Bioorg. Med. Chem. Lett. 2000, 10, 2179.
         | CrossRef | 1:CAS:528:DC%2BD3cXmsFKksbc%3D&md5=e317bb43702830c2d9e1915be2aaf1beCAS |

[120]  S. Rostamnia, K. Lamei, Synthesis 2011, 3080.
         | CrossRef | 1:CAS:528:DC%2BC3MXhsFCrtb3E&md5=fd6c457b21bcc6459a457990ea77158bCAS |

[121]  H. Liu, Y. Zou, Y. Hu, D.-Q. Shi, J. Heterocycl. Chem. 2011, 48, 877.
         | CrossRef | 1:CAS:528:DC%2BC3MXptlWqsrY%3D&md5=3b28a7e97c272b75c2d96fc629e114eeCAS |

[122]  D.-N. Zhang, J.-T. Li, Y.-L. Song, H.-M. Liu, H.-Y. Li, Ultrason. Sonochem. 2012, 19, 475.
         | CrossRef | 1:CAS:528:DC%2BC38XivVKksw%3D%3D&md5=5cc58d59e5ee89981dfc34e367d8f62dCAS |



Rent Article (via Deepdyve) Export Citation Cited By (1)