Mannich reaction: A versatile and convenient approach to bioactive skeletons

Journal of Chemical Sciences

Volumn 125, Issue 3, 2013, Pages 467-482

  Subramaniapillai, Selva Ganesan ^a  

^a SASTRA UNIVERSITY   (India)

Author keywords

antimalarial; antitubercular; antitumour; bioactive molecules; Mannich bases; Mannich reaction

Indexed keywords

ANTI TUBERCULARS; ANTIMALARIAL; ANTITUMOUR; BIOACTIVE MOLECULES; MANNICH BASIS; MANNICH REACTIONS;

MOLECULES;

CHEMICAL REACTIONS;

EID: 84879818166     PISSN: 09743626     EISSN: 09737103     Source Type: Journal    
DOI: 10.1007/s12039-013-0405-y     Document Type: Article

References (132)

1. (a) Brigger I, Dubernet C and Couvreur P 2002 Adv. Drug Deliver. Rev. 54 631
2. Vauthier C, Dubernet C, Chauvierre C, Brigger I and Couvreur P 2003 J. Control. Release 93 151
3. Tramontini M 1973 Synthesis 703
4. Mannich C and Krosche W 1912 Arch. Pharm. 250 647
5. (a) Nie J, Guo H-C, Cahard D and Ma J-A 2011 Chem. Rev. 111 455
6. Kobayashi S, Mori Y, Fossey J S and Salter M M 2011 Chem. Rev. 111 2626
7. Candeias N R, Montalbano F, Cal P M S D and Gois P M P 2010 Chem. Rev. 110 6169
8. Kang Y K and Kim D Y 2011 Tetrahedron Lett. 52 2356
9. Yang Y, Phillips D P and Pan S 2011 Tetrahedron Lett. 52 1549
10. Handa S, Gnanadesikan V, Matsunaga S and Shibasaki M 2010 J. Am. Chem. Soc. 132 4925
11. Hashimoto T, Kimura H, Nakatsu H and Maruoka K 2011 J. Org. Chem. 76 6030
12. Colpaert F, Mangelinckx S and Kimpe N D 2010 Org. Lett. 12 1904
13. Shibasaki M and Kanai M 2008 Chem. Rev. 108 2853
14. Notz W, Tanaka F, Watanabe S, Chowdari N S, Turner J M, Thayumanavan R and Barbas III C F 2003 J. Org. Chem. 68 9624
15. (a) Bur S K and Martin S F 2001 Tetrahedron 57 3221
16. Martin S F 2002 Acc. Chem. Res. 35 895
17. Liu M and Sibi M P 2002 Tetrahedron 58 7991
18. Kobayashi S and Ishitani H 1999 Chem. Rev. 99 1069
19. Ollevier T and Nadeau E 2007 Org. Biomol. Chem. 5 3126
20. (a) Arend M, Westermann B and Risch N 1998 Angew. Chem. Int. Ed. 37 1044
21. Córdova A 2004 Acc. Chem. Res. 37 102
22. Notz W, Tanaka F and Barbas III C F 2004 Acc. Chem. Res. 37 580
23. Ruan S-T, Luo J-M, Du Y and Huang P-Q 2011 Org. Lett. 13 4938
24. Ranieri B, Curti C, Battistini L, Sartori A, Pinna L, Casiraghi G and Zanardi F 2011 J. Org. Chem. 76 10291
25. Wang C-J, Dong X-Q, Zhang Z-H, Xue Z-Y and Teng H-L 2008 J. Am. Chem. Soc. 130 8606
26. (a) Periasamy M, Ganesan S S and Suresh S 2010 Tetrahedron: Asymmetry 21 385
27. De Graaff C, Ruijter E and Orru R V A 2012 Chem. Soc. Rev. 41 3969
28. Periasamy M, Suresh S and Ganesan S S 2006 Tetrahedron: Asymmetry 17 1323
29. Annunziata R, Benaglia M, Cinquini M, Cozzi F and Raimondi L 1993 Tetrahedron Lett. 34 6921
30. Bravo P, Fustero S, Guidetti M, Volonterio A and Zanda M 1999 J. Org. Chem. 64 8731
31. (a) Karmakar B and Banerji J 2011 Tetrahedron Lett. 52 4957
32. Kidwai M, Mishra N K, Bansal V, Kumar A and Mozumdar S 2009 Tetrahedron Lett. 50 1355
33. Krishnan G R, Thomas J and Sreekumar K 2009 ARKIVOC x 106
34. Huang P-J J, Youssef D, Cameron T S and Jha A 2008 ARKIVOC xvi 165
35. Hayashi Y, Tsuboi W, Shoji M and Suzuki N 2003 J. Am. Chem. Soc. 125 11208
36. Cimarelli C, Fratoni D and Palmieri G 2011 Tetrahedron: Asymmetry 22 1560
37. Ibrahem I, Zou W, Casas J, Sundén H and Córdova A 2006 Tetrahedron 62 357
38. (a) Kumar A, Gupta M K and Kumar M 2012 Green Chem. 14 290
39. Yang J W, Chandler C, Stadler M, Kampen D and List B 2008 Nature 452 453
40. Srinivas N and Bhandari K 2008 Tetrahedron Lett. 49 7070
41. Indumathi S, Perumal S and Menéndez J C 2011 Tetrahedron 67 7101
42. Schulz K, Ratjen L and Martens J 2011 Tetrahedron 67 546
43. Indumathi S, Perumal S, Banerjee D, Yogeeswari P and Sriram D 2009 Eur. J. Med. Chem. 44 4978
44. Veverková E, Štrasserová J, Šebesta R and Toma Š 2010 Tetrahedron: Asymmetry 21 58
45. (a) Jiang C, Zhong F and Lu Y 2012 Beilstein J. Org. Chem. 8 1279
46. Kang Y K and Kim D Y 2009 J. Org. Chem. 74 5734
47. Zhang Z -W, Lu G, Chen M-M, Lin N, Li Y-B, Hayashi T and Chan A S C 2010 Tetrahedron: Asymmetry 21 1715
48. Bai S, Liang X, Song B, Bhadury P S, Hu D and Yang S 2011 Tetrahedron: Asymmetry 22 518
49. Goswami P and Das B 2009 Tetrahedron Lett. 50 2384
50. Wu C, Fu X and Li S 2011 Tetrahedron: Asymmetry 22 1063
51. Wu C, Fu X, Ma X, Li S and Li C 2010 Tetrahedron Lett. 51 5775
52. Fu A, Li H, Si H, Yuan S and Duan Y 2008 Tetrahedron: Asymmetry 19 2285
53. (a) Verkade J M M, van Hemert L J C, Quaedflieg P J L M and Rutjes F P J T 2008 Chem. Soc. Rev. 37 29
54. Panday S K 2011 Tetrahedron: Asymmetry 22 1817
55. List B 2002 Tetrahedron 58 5573
56. Gaunt M J, Johansson C C C, McNally A and Vo N T 2007 Drug Discov. Today 12 8
57. Pellissier H 2007 Tetrahedron 63 9267
58. (a) Werder M, Hauser H and Carreira E M 2005 J. Med. Chem. 48 6035
59. Roers R and Verdine G L 2001 Tetrahedron Lett. 42 3563
60. Nicolaou K C, Dai W-M and Guy R K 1994 Angew. Chem. Int. Ed. 33 15
61. Cardillo G and Tomasini C 1996 Chem. Soc. Rev. 25 117
62. Sarhan A E-W A O, Abdel-Hafez S H, El-Sherief H and Aboel-Fadl T 2006 Synthetic Commun. 36 987
63. Lal B, Gund V G, Bhise N B and Gangopadhyay A K 2004 Bioorg. Med. Chem. 12 1751
64. Sumalatha Y, Reddy P P, Reddy R and Satyanarayana B 2009 ARKIVOC vii 143
65. Negm N A, Morsy S M I and Said M M 2005 Bioorg. Med. Chem. 13 5921
66. Ferlin M G, Chiarelotto G, Antonucci F, Caparrotta L and Froldi G 2002 Eur. J. Med. Chem. 37 427
67. Holla B S, Veerendra B, Shivananda M K and Poojary B 2003 Eur. J. Med. Chem. 38 759
68. Malinka W, Świa̧tek P, Filipek B, Sapa J, Jezierska A and Koll A 2005 Il Farmaco 60 961
69. Baramee A, Coppin A, Mortuaire M, Pelinski L, Tomavo S and Brocard J 2006 Bioorg. Med. Chem. 14 1294
70. Chernov S V, Shults E E, Shakirov M M, Bagrjanskaja I Y, Gatilov Y V and Tolstikov G A 2003 ARKIVOC xiii 172
71. Martin S F and Bur S K 1999 Tetrahedron 55 8905
72. Hayashi Y, Urushima T, Shin M and Shoji M 2005 Tetrahedron 61 11393
73. Babu T H, Rao V R S, Tiwari A K, Babu K S, Srinivas P V, Ali A Z and Rao J M 2008 Bioorg. Med. Chem. Lett. 18 1659
74. Kotecka B M, Barlin G B, Edstein M D and Rieckmann K H 1997 Antimicrob. Agents Ch. 41 1369 and references cited therein
75. Pacorel B, Leung S C, Stachulski A V, Davies J, Vivas L, Lander H, Ward S A, Kaiser M, Brun R and O'Neill P M 2010 J. Med. Chem. 53 633 and references cited therein
76. Chipeleme A, Gut J, Rosenthal P J and Chibale K 2007 Bioorg. Med. Chem. 15 273 and references cited therein
77. Guantai E M, Ncokazi K, Egan T J, Gut J, Rosenthal P J, Bhampidipati R, Kopinathan A, Smith P J and Chibale K 2011 J. Med. Chem. 54 3637 and references cited therein
78. O'Neill P M, Mukhtar A, Stocks P A, Randle L E, Hindley S, Ward S A, Storr R C, Bickley J F, O'Neil I A, Maggs J L, Hughes R H, Winstanley P A, Bray P G and Park B K 2003 J. Med. Chem. 46 4933
79. Lopes F, Capela R, Gonçaves J O, Horton P N, Hursthouse M B, Iley J, Casimiro C M, Bom J and Moreira R 2004 Tetrahedron Lett. 45 7663
80. Saha C N, Bhattacharya S and Chetia D 2009 Int. J. ChemTech Res. 1 322
81. (a) Wenzel N I, Chavain N, Wang Y, Friebolin W, Maes L, Pradines B, Lanzer M, Yardley V, Brun R, Herold-Mende C, Biot C, Tóth K and Davioud-Charvet E 2010 J. Med. Chem. 53 3214
82. Miroshnikova O V, Hudson T H, Gerena L, Kyle D E and Lin A J 2007 J. Med. Chem. 50 889
83. (a) Shchekotikhin A E, Shtil A A, Luzikov Y N, Bobrysheva T V, Buyanov V N and Preobrazhenskaya M N 2005 Bioorg. Med. Chem. 13 2285
84. Kearney A S, Patel K and Palepu N R 1996 Int. J. Pharm. 127 229
85. Yogeeswari P, Sriram D, Kavya R and Tiwari S 2005 Biomed. Pharmacother. 59 501
86. Gul H I, Vepsalainen J, Gul M, Erciyas E and Hanninen O 2000 Pharm. Acta. Helv. 74 393
87. Yamakawa T, Ideue E, Iwaki Y, Sato A, Tokuyama H, Shimokawa J and Fukuyama T 2011 Tetrahedron 67 6547
88. Shaw A Y, Chang C-Y, Hsu M-Y, Lu P-J, Yang C-N, Chen H-L, Lo C-W, Shiau C-W and Chern M-K 2010 Eur. J. Med. Chem. 45 2860
89. Chen H-L, Chang C-Y, Lee H-T, Lin H-H, Lu P-J, Yang C-N, Shiau C-W and Shaw A Y 2009 Bioorg. Med. Chem. 17 7239 and references cited therein
90. Euzébio F P G, Santos F J L D, Piló-Veloso D, Alcântara A F C, Ruiz A L T G, Carvalho J E, Foglio M A, Ferreira-Alves D L and Fátima A 2010 Bioorg. Med. Chem. 18 8172
91. Longshaw A I, Adanitsch F, Gutierrez J A, Evans G B, Tyler P C and Schramm V L 2010 J. Med. Chem. 53 6730
92. (a) Wang Z, Shi X-H, Wang J, Zhou T, Xu Y-Z, Huang T-T, Li Y-F, Zhao Y-L, Yang L, Yang S-Y, Yu L-T and Wei Y-Q 2011 Bioorg. Med. Chem. Lett. 21 1097
93. Yoshida M, Hayakawa I, Hayashi N, Agatsuma T, Oda Y, Tanzawa F, Iwasaki S, Koyama K, Furukawa H, Kurakata S and Sugano Y 2005 Bioorg. Med. Chem. Lett. 15 3328
94. (a) Kumbhare R M, Kumar K V, Ramaiah M J, Dadmal T, Pushpavalli S N C V L, Mukhopadhyay D, Divya B, Devi T A, Kosurkar U and Pal-Bhadra M 2011 Eur. J. Med. Chem 46 4258
95. Dake S A, Raut D S, Kharat K R, Mhaske R S, Deshmukh S U and Pawar R P 2011 Bioorg. Med. Chem. Lett. 21 2527
96. Reddy C B, Kumar K S, Kumar M A, Reddy M V N, Krishna B S, Naveen M, Arunasree M K, Reddy C S, Raju C N and Reddy C D 2012 Eur. J. Med. Chem. 47 553
97. Steere J A, Sampson P B and Honek J F 2002 Bioorg. Med. Chem. Lett. 12 457
98. Jin L, Song B, Zhang G, Xu R, Zhang S, Gao X, Hu D and Yang S 2006 Bioorg. Med. Chem. Lett. 16 1537
99. Reddy M V B, Su C-R, Chiou W-F, Liu Y-N, Chen R Y-H, Bastow K F, Lee K-H and Wu T-S 2008 Bioorg. Med. Chem. 16 7358
100. (a) Chen Y-L, Huang S-T, Sun F-M, Chiang Y-L, Chiang C-J, Tsai C-M and Weng C-J 2011 Eur. J. Pharm. Sci. 43 188
101. Almajan G L, Barbuceanu S F, Almajan E R, Draghici C and Saramet G 2009 Eur. J. Med. Chem. 44 3083
102. Ashok M, Holla B S and Poojary B 2007 Eur. J. Med. Chem. 42 1095
103. Joshi S, Khosla N, Khare D and Sharda R 2005 Bioorg. Med. Chem. Lett. 15 221
104. Srivastava B K, Kapadnis P B, Pandya P and Lohray V B 2004 Eur. J. Med. Chem. 39 989
105. Idhayadhulla A, Kumar R S, Nasser A J A, Selvin J and Manilal A 2011 Arabian J. Chem. doi: 10.1016/j.arabjc.2010.12.025
106. Lóránd T, Kocsis B, Sohár P, Nagy G, Kispál G, Krane H-G, Schmitt H and Weckert E 2001 Eur. J. Med. Chem. 36 705
107. Lóránd T, Osz E, Kispál G, Nagy G, Weckert E, Luebbert D, Meents A, Kocsis B and Prókai L 2004 ARKIVOC vii 34
108. Singh U K, Pandeya S N, Singh A, Srivastava B K and Pandey M 2010 Int. J. Pharm. Sci. Drug Res. 2 151
109. Ravichandran V, Mohan S and Kumar K S 2007 ARKIVOC xiv 51
110. Terzioǧlu N, Karali N, Gürsoy A, Pannecouque C, Leysen P, Paeshuyse J, Neyts J and Clercq E D 2006 ARKIVOC i 109
111. Joshi S, Khosla N and Tiwari P 2004 Bioorg. Med. Chem. 12 571
112. Karthikeyan M S, Prasad D J, Poojary B, Bhat K S, Holla B S and Kumari N S 2006 Bioorg. Med. Chem. 14 7482
113. Plech T, Wujec M, Siwek A, Kosikowska U and Malm A 2011 Eur. J. Med. Chem. 46 241
114. Mazzei M, Nieddu E, Miele M, Balbi A, Ferrone M, Fermeglia M, Mazzei M T, Pricl S, Colla P L, Marongiu F, Ibba C and Loddo R 2008 Bioorg. Med. Chem. 16 2591
115. Panja S K, Maiti S, Drew M G B and Bandyopadhyay C 2009 Tetrahedron 65 1276
116. Rai U S, Isloor A M, Shetty P, Isloor N, Malladi S and Fun H-K 2010 Eur. J. Med. Chem. 45 6090
117. Saraswathi M, Rohini R M, Ranaprathapsingh and Nayeem N 2010 Pak. J. Pharm. Sci. 23 459
118. Joshi S, Manikpuri A D and Tiwari P 2007 Bioorg. Med. Chem. Lett. 17 645
119. Mete E, Gul H I, Bilginer S, Algul O, Topaloglu M E, Gulluce M and Kazaz C 2011 Molecules 16 4660
120. (a) Aboul-Fadl T and Bin-Jubair F A S 2010 Int. J. Res. Pharm. Sci. 1 113 and references cited therein
121. Tambo-ong A, Chopra S, Glaser B T, Matsuyama K, Tran T and Madrid P B 2011 Bioorg. Med. Chem. Lett. 21 5697
122. Parthiban P, Subalakshmi V, Balasubramanian K, Islam M N, Choi J S and Jeong Y T 2011 Bioorg. Med. Chem. Lett. 21 2287
123. Kumar G V S, Prasad Y R, Mallikarjuna B P and Chandrashekar S M 2010 Eur. J. Med. Chem. 45 5120
124. (a) Allison M C, Howatson A G, Torrance C J, Lee F D and Russell R I 1992 New Engl. J. Med. 327 749
125. Duflos M, Nourrisson M-R, Brelet J, Courant J, LeBaut G, Grimaud N and Petit J-Y 2001 Eur. J. Med. Chem. 36 545
126. Sujith K V, Rao J N, Shetty P and Kalluraya B 2009 Eur. J. Med. Chem. 44 3697
127. Reddy M V B, Hwang T-L, Leu Y-L, Chiou W-F and Wu T-S 2011 Bioorg. Med. Chem. 19 2751
128. Fabio R D, Alvaro G, Bertani B, Donati D, Pizzi D M, Gentile G, Pentassuglia G, Giacobbe S, Spada S, Ratti E, Corsi M, Quartaroli M, Barnaby R J and Vitulli G 2007 Bioorg. Med. Chem. Lett. 17 1176
129. Babu M, Pitchumani K and Ramesh P 2012 Bioorg. Med. Chem. Lett. 22 1263
130. Obniska J, Byrtus H, Kamiński K, Pawşowski M, Szczesio M and Karolak-Wojciechowska J 2010 Bioorg. Med. Chem. 18 6134
131. Prakash C R and Raja S 2011 Eur. J. Med. Chem. 46 6057
132. Byrtus H, Obniska J, Czopek A, Kamiński K and Pawşowski M 2011 Bioorg. Med. Chem. 19 6149