Recent Advances in the Chemistry and Pharmacology of Cryptolepine
199
4. Dhanabal T, Sangeetha R, Mohan PS (2006) Heteroatom directed photoannulation: synthesis
of indoloquinoline alkaloids: cryptolepine, cryptotackeine, cryptosanguinolentine, and their
methyl derivatives. Tetrahedron 62:6258
5. Parvatkar PT, Parameswaran PS (2016) Indoloquinolines: possible biogenesis from common
indole precursors and their synthesis using domino strategies. Curr Org Synth 13:58
6. Lavrado, J, Moreira R, Paulo A (2011) Synthetic strategies towards bioactive indolo[3,2b]quinolines. In: Carreiras M do C, Marco-Contelles J (eds) Heterocyclic targets in advanced
organic synthesis, vol 5. Research Signpost, Tivandrum, India, p 109
7. Volvoikar PS, Pravatkar PT, Tilve SG (2013) Tandem reductive cyclization-dehydration
approach for the synthesis of cryptolepine hydroiodide and its analogues. Eur J Org Chem:2172
8. Parvatkar PT, Majik MS (2014) Microwave-assisted reductive cyclization: an easy entry to the
indoloquinolines and spiro[2H-indole-2,3 -oxindole]. RSC Adv 4:22481
9. Holt SJ, Petrow V (1947) Carbazoles, carbolines and related compounds. Part 1. Quindoline
derivatives. J Chem Soc:607
10. Onyeibor O, Croft SL, Dodson HI, Feiz-Haddad M, Kendrick H, Millington NJ, Parapini S,
Phillips RM, Seville S, Shnyder SD, Taramelli D, Wright CW (2005) Synthesis of some cryptolepine analogues, assessment of their antimalarial and cytotoxic activities and consideration
of their antimalarial mode of action. J Med Chem 48:2701
11. Bogányi B, Kámán J (2013) A concise synthesis of indoloquinoline skeletons applying two
consecutive Pd-catalyzed reactions. Tetrahedron 69:9512
12. Wippich J, Truchan N, Bach T (2016) Rhodium catalyzed N-tert-butoxycarbonyl (Boc)
amination by directed C-H bond activation. Adv Synth Catal 358:2083
13. Yonekura K, Shinoda M, Yonekura Y, Tsuchimoto T (2018) Indium-catalyzed annulations of
o-acylanilines with alkoxyheteroarenes: Synthesis of heteroaryl[b]quinoline and subsequent
transformation to cryptolepine derivatives. Molecules 23:838
14. Shuvalov VY, Rupp AS, Kuratova AS, Fisyuk AS, Kuratova AK, Nefedov AA, Sagitullina GP
(2019) Synthesis and optical properties of the alkaloid quindoline, its structural analogues and
substituted δ-carbolines. ChemistrySelect 4:1696
15. Gibbons S, Fallah F, Wright CW (2003) Cryptolepine hydrochloride: a potent antimycobacterial
alkaloid derived from Cryptolepis sanguinolenta. Phytother Res 17:434
16. Appunni SR, Rubens M, Chandana S, Singh HN, Swarup V (2017) Targeting PknB, an
eukaryotic-like serine/threonine protein kinase of Mycobacterium tuberculosis with phytomolecules. Comp Biol Chem 67:200
17. Gurung AB, Mylliemngap BJ, Battercharjee A, Ali MA Al-Hemaid FMA (2015) Interactome
analysis and design of inhibitors against selected protein targets of Ser/Thr protein kinse (STPK)
signalling pathways in Mycobacterium tuberculosis H37Rv. Genet Mol Res 14:10390
18. Bolden S, Jr, Zhu XY, Etukala JR, Boateng C, Mazu T, Flores-Rozas H, Jacob MR, Khan SI,
Walker LA Ablordeppy SY (2013) Structure-activity relationship (SAR) and preliminary mode
of action studies of 3-substituted benzylthioquinolinium iodides as anti-opportunistic infection
agents. Eur J Med Chem 70:130
19. Bolden S, Boateng CA, Zhu ZY, Etukala JR, Eyunni SK, Jacob MR, Khan SI, Ablordeppy SY
(2013) CoMFA studies and in vitro evaluation of some 3-substituted benzylthioquinolinium
salts as cryptococcal agents. Bioorg Med Chem 21:7194
20. Fernandes HD, Filomena B, Silvia L, Gabriel BC, Betuel S (2020) A systematic review of
in vitro activity of medicinal plants from sub-Saharan Africa against Campylobacter spp.
eCAM, 20209485364
21. Nuthakki VJ, Mudududdla R, Sharma A, Kumar A, Bharate SB (2019) Synthesis and biological evaluation of indoloquinoline alkaloid cryptolepine and its bromo-derivative as dual
chlolinesterase inhibitors. Bioorg Chem 90:103062
22. Bierer DE, Fort DM, Mendez CD, Luo J, Imbach PA, Dubenko LG, Jolad SD, Gerber RE,
Litva J, Lu Q, Zhang P, Reed MJ, Wladeck N, Bruening RC, Noamesi BK, Hector RF, Carlson
TJ, King SR (1998) Ethnobotanical-directed discovery of the antihyperglycemic properties of
cryptolepine: its isolation from Cryptolepis sanguinolenta, synthesis and in vitro and in vivo
activities. J Med Chem 41:894
199
4. Dhanabal T, Sangeetha R, Mohan PS (2006) Heteroatom directed photoannulation: synthesis
of indoloquinoline alkaloids: cryptolepine, cryptotackeine, cryptosanguinolentine, and their
methyl derivatives. Tetrahedron 62:6258
5. Parvatkar PT, Parameswaran PS (2016) Indoloquinolines: possible biogenesis from common
indole precursors and their synthesis using domino strategies. Curr Org Synth 13:58
6. Lavrado, J, Moreira R, Paulo A (2011) Synthetic strategies towards bioactive indolo[3,2b]quinolines. In: Carreiras M do C, Marco-Contelles J (eds) Heterocyclic targets in advanced
organic synthesis, vol 5. Research Signpost, Tivandrum, India, p 109
7. Volvoikar PS, Pravatkar PT, Tilve SG (2013) Tandem reductive cyclization-dehydration
approach for the synthesis of cryptolepine hydroiodide and its analogues. Eur J Org Chem:2172
8. Parvatkar PT, Majik MS (2014) Microwave-assisted reductive cyclization: an easy entry to the
indoloquinolines and spiro[2H-indole-2,3 -oxindole]. RSC Adv 4:22481
9. Holt SJ, Petrow V (1947) Carbazoles, carbolines and related compounds. Part 1. Quindoline
derivatives. J Chem Soc:607
10. Onyeibor O, Croft SL, Dodson HI, Feiz-Haddad M, Kendrick H, Millington NJ, Parapini S,
Phillips RM, Seville S, Shnyder SD, Taramelli D, Wright CW (2005) Synthesis of some cryptolepine analogues, assessment of their antimalarial and cytotoxic activities and consideration
of their antimalarial mode of action. J Med Chem 48:2701
11. Bogányi B, Kámán J (2013) A concise synthesis of indoloquinoline skeletons applying two
consecutive Pd-catalyzed reactions. Tetrahedron 69:9512
12. Wippich J, Truchan N, Bach T (2016) Rhodium catalyzed N-tert-butoxycarbonyl (Boc)
amination by directed C-H bond activation. Adv Synth Catal 358:2083
13. Yonekura K, Shinoda M, Yonekura Y, Tsuchimoto T (2018) Indium-catalyzed annulations of
o-acylanilines with alkoxyheteroarenes: Synthesis of heteroaryl[b]quinoline and subsequent
transformation to cryptolepine derivatives. Molecules 23:838
14. Shuvalov VY, Rupp AS, Kuratova AS, Fisyuk AS, Kuratova AK, Nefedov AA, Sagitullina GP
(2019) Synthesis and optical properties of the alkaloid quindoline, its structural analogues and
substituted δ-carbolines. ChemistrySelect 4:1696
15. Gibbons S, Fallah F, Wright CW (2003) Cryptolepine hydrochloride: a potent antimycobacterial
alkaloid derived from Cryptolepis sanguinolenta. Phytother Res 17:434
16. Appunni SR, Rubens M, Chandana S, Singh HN, Swarup V (2017) Targeting PknB, an
eukaryotic-like serine/threonine protein kinase of Mycobacterium tuberculosis with phytomolecules. Comp Biol Chem 67:200
17. Gurung AB, Mylliemngap BJ, Battercharjee A, Ali MA Al-Hemaid FMA (2015) Interactome
analysis and design of inhibitors against selected protein targets of Ser/Thr protein kinse (STPK)
signalling pathways in Mycobacterium tuberculosis H37Rv. Genet Mol Res 14:10390
18. Bolden S, Jr, Zhu XY, Etukala JR, Boateng C, Mazu T, Flores-Rozas H, Jacob MR, Khan SI,
Walker LA Ablordeppy SY (2013) Structure-activity relationship (SAR) and preliminary mode
of action studies of 3-substituted benzylthioquinolinium iodides as anti-opportunistic infection
agents. Eur J Med Chem 70:130
19. Bolden S, Boateng CA, Zhu ZY, Etukala JR, Eyunni SK, Jacob MR, Khan SI, Ablordeppy SY
(2013) CoMFA studies and in vitro evaluation of some 3-substituted benzylthioquinolinium
salts as cryptococcal agents. Bioorg Med Chem 21:7194
20. Fernandes HD, Filomena B, Silvia L, Gabriel BC, Betuel S (2020) A systematic review of
in vitro activity of medicinal plants from sub-Saharan Africa against Campylobacter spp.
eCAM, 20209485364
21. Nuthakki VJ, Mudududdla R, Sharma A, Kumar A, Bharate SB (2019) Synthesis and biological evaluation of indoloquinoline alkaloid cryptolepine and its bromo-derivative as dual
chlolinesterase inhibitors. Bioorg Chem 90:103062
22. Bierer DE, Fort DM, Mendez CD, Luo J, Imbach PA, Dubenko LG, Jolad SD, Gerber RE,
Litva J, Lu Q, Zhang P, Reed MJ, Wladeck N, Bruening RC, Noamesi BK, Hector RF, Carlson
TJ, King SR (1998) Ethnobotanical-directed discovery of the antihyperglycemic properties of
cryptolepine: its isolation from Cryptolepis sanguinolenta, synthesis and in vitro and in vivo
activities. J Med Chem 41:894