Synthesis and Anticancer Properties of Functionalized 1,6-Naphthyridines

Springer Science and Business Media LLC - Tập 379 - Trang 1-75 - 2021
Mallu Lavanya1,2, Chong Lin1, Jincheng Mao1, Dhakshanamurthy Thirumalai3, Sreenath Reddy Aabaka1, Xiaojiang Yang1, Jinhua Mao1, Zhiyu Huang2, Jinzhou Zhao1
1State Key Laboratory of Oil and Gas Reservoir Geology and Exploitation, Southwest Petroleum University, Chengdu, People’s Republic of China
2School of Chemistry and Chemical Engineering, Southwest Petroleum University, Chengdu, People’s Republic of China
3Department of Chemistry, Thiruvalluvar University, Vellore, India

Tóm tắt

The burgeoning interest in synthesis and biological applications of 1,6-naphthyridines reflects the importance of 1,6-naphthyridines in the synthetic as well as medicinal chemistry fields. Specially, 1,6-naphthyridines are pharmacologically active, with variety of applications such as anticancer, anti-human immunodeficiency virus (HIV), anti-microbial, analgesic, anti-inflammatory and anti-oxidant activities. Although collective recent synthetic developments have paved a path to a wide range of functionalized 1,6-naphthyridines, a complete correlation of synthesis with biological activity remains elusive. The current review focuses on recent synthetic developments from the last decade and a thorough study of the anticancer activity of 1,6-naphthyridines on different cancer cell lines. Anticancer activity has been correlated to 1,6-naphthyridines using the literature on the structure–activity relationship (SAR) along with molecular modeling studies. Exceptionally, at the end of this review, the utility of 1,6-naphthyridines displaying activities other than anticancer has also been included as a glimmering extension.

Tài liệu tham khảo

Kumar D, Jain SK (2016) Curr Med Chem 23:4338–4394 Litvinov VP (2006) Adv Heterocycl Chem 91:189–300 Garcia-Valverde M, Torroba T (2008) Molecules 10:318–320 Zheng L, Bin Y, Wang Y, Hua R (2016) J Org Chem 81:8911–8919 Bracher F, Mink K (1995) Liebigs Ann 20:645–647 Bennasar ML, Roca T, Zulaica E, Monerris M (2004) Tetrahedron 60:6785–6789 Gross H, Goeger DE, Hills P, Mooberry SL, Ballantine DL, Murray TF, Valeriote FA, Gerwick WH (2006) J Nat Prod 69:640–644 Zhang A, Ding C, Cheng C, Yao Q (2007) J Comb Chem 9:916–919 Kulakov IV, Shatsauskas AL, Matsukevich MV, Palamarchuk IV, Seilkhanov TM, Gatilov YV, Fisyuk AS (2017) Synthesis 49:3700–3709 Okuma K, Oba A, Kuramoto R, Iwashita H (2017) Eur J Org Chem 2017:6885–6888 Wang HY, Shi JJ, Wang C, Zhang XX, Wan Y, Wu H (2012a) Dye Pigment 95:268–274 Patil SR, Shelar DP, Rote RV, Jachak MN (2011) J Fluoresc 21:2037–2052 Padhi SK, Tanaka K (2011) Inorg Chem 50:10718–10723 Noravyan AS, Paronikyan EG, Vartanyan SA (1986) Search New Drugs 85:439–448 Paudler WW, Kress TJ (1970) Adc Heterocycl Chem 11:123–175 Paudler WW, Sheets RM (1983) Adc Heterocycl Chem 33:148–165 Hamada Y, Takeuchi I (2000) J Pharm Soc Jpn 120:206–223 Ramhari VR, Sandeep MB, Deepak PS, Sandeep RP, Raghunath BT, Madhukar NJ (2011) J Heterocyclic Chem 48:301–307 Madhukar NJ, Sandeep MB, Muddassar AK, Raghunath BT (2011) J Heterocyclic Chem 48:295–300 Bodrin GV, Matveeva AG, Goryunov EI, Pasechnik MP, Aysin RR, Turanov AN, Karandashev VK, Savin ED, Peregudov AS, Nelyubina YV, Brel VK (2016) Chem Heterocycl Compd 52:583–591 Hauser CR, Reynolds GA (1950) J Org Chem 15:1224–1232 Manoj M, Prasad KJR (2012) Synth Commun 42:434–446 Prabha K, Prasad KJR (2012) Synth Commun 42:2277–2289 Varlamov AV, Guranova NI, Listratova AV, Borisova TN, Khrustalev VN, Titov AA, Voskressensky LG (2014) Chem Heterocycl Compd 50:264–270 Rajanarendar E, Ramakrishna S, Kishore B (2014) J Heterocyclic Chem 51:1415–1420 Dore A, Asproni B, Scampuddu A, Gessi S, Murineddu G, Cichero E, Fossa P, Merighi S, Bencivenni S, Pinna GA (2016) Bioorg Med Chem 24:5291–5301 Hassaneen HM, Wardkhan WW, Mohammed YS (2012) Heterocycles 85:2933–2947 Vasilev LS, Surzhikov FE, Baranin SV, Dorokhov VA (2013) Russ Chem Bull Int Ed 62:1255–1261 Hassaneen HM, Wardkhan WW, Mohammed YS (2013) Z Naturforsch 68b:895–904 Khakwani S, Aslam S, Mussadiq S, Shahi MN, Perveen N, Benardino AMR, Khan MA (2016) Asian J Chem 28:2601–2604 Prabha K (2016) Med Chem 6:62–71 Ghotekar BK, Ghagare MG, Toche RB, Jachak MN (2010) Monatsh Chem 141:169–175 Ravi M, Chauhan P, Singh S, Kant R, Yadav PP (2016) RSC Adv 6:48774–48778 Selva Kumar AKMM, Rajkumar R, Rajendran SP (2015) Arch Appl Sci Res 7:60–64 Sarkar S, Das DK, Khan AT (2013) Eur J Org Chem 2013:6823–6830 Verma AK, Jha RR, Chaudhary R, Tiwari RK, Reddy KSK, Danodia A (2012) J Org Chem 77:8191–8205 Hoplamaz E, Keskin S, Balci M (2017) Eur J Org Chem 2017:1489–1497 Das P, Mukhopadhyay C (2014) Curr Microw Chem 1:98–109 Mishra A, Rastogi N, Batra S (2012) Tetrahedron 68:2146–2154 Sporar J, Bezensek J, Ursic U, Golobic A, Svete J, Stanovnik B (2011) Heterocycles 84:449–459 Moustafa MS, Al-Mousawi SM, Hilmy NM, Ibrahim YA, Liermann JC, Meier H, Elnagdi MH (2013) Molecule 18:276–286 Abdel Hameed AM (2015) Environ Chem Lett 13:125–129 Dotsenko VV, Ismiev AI, Khrustaleva AN, Frolov KA, Krivokolysko SG, Chigorina EA, Snizhko AP, Gromenko VM, Bushmarinov IS, Askerov RK, Pekhtereva TM, Suykov SY, Papayanina ES, Mazepa AV, Magerramov AM (2016) Chem Heterocycl Compd 52:473–483 Suneel Kumar Y, Nawaz Khan F (2017a) Catal Lett 147:919–925 Yu Y, Su R, Wang L, Qi W, He Z (2010) Med Chem Res 19:1233–1244 Lukka PB, Paxton JW, Kestell P, Baguley BC (2012) Cancer Chemother Pharmacol 70:151–160 Feng W, Satyanarayana M, Cheng L, Liu A, Tsai YC, Liu LF, LaVoie EJ (2008) Bioorganic Med Chem 16:9295–9301 Feng W, Satyanarayana M, Tsai YC, Liu AA, Liu LF, LaVoie EJ (2009) Eur J Med Chem 44:3433–3438 Rudys S, Rios-Luci C, Perez-Roth E, Cikotiene I, Padron JM (2010) Bioorg Med Chem Lett 20:1504–1506 Kiselev E, Dexheimer TS, Pommier Y, Cushman M (2010) J Med Chem 53:8716–8726 Liu Q, Chang JW, Wang J, Kang SA, Thoreen CC, Markhard A, Hur W, Zhang J, Sim T, Sabatini DM, Gray NS (2010a) J Med Chem 53:7146–7155 Liu Q, Chang JW, Wang J, Kang SA, Thoreen CC, Markhard A, Hur W, Zhang J, Sim T, Sabatini DM, Gray NS (2010b) J Med Chem 2:7146–7155 Lin S, Han F, Liu P, Tao J, Zhong X, Liu X, Yi C, Xu H (2014) Bioorg Med Chem Lett 24:790–793 Hunt JA, Kallashi F, Ruzek RD, Sinclair PJ, Ita I, McCormick SX, Pivnichny JV, Hop CECA, Kumar S, Wang Z, Keefe SJO, Neill EAO, Porter G, Thompson JE, Woods A, Zaller DM, Doherty JB (2003) Bioorg Med Chem Lett 13:467–470 Wang Y, Xu ZL, Ai J, Peng X, Lin JP, Ji YC, Geng MY, Long YQ (2013) Org Biomol Chem 11:1545–1562 Boezio AA, Copeland KW, Rex K, Albrecht BK, Bauer D, Bellon SF, Boezio C, Broome MA, Choquette D, Coxon A, Dussault I, Hirai S, Lewis R, Lin M-HJ, Lohman J, Liu J, Peterson EA, Potashman M, Shimanovich R, Teffera Y, Whittington DA, Vaida KR, Harmange JC (2016) J Med Chem 59:2328–2342 Elsayed MSA, Nielsen JJ, Park S, Park J, Liu Q, Kim CH, Pommier Y, Agama K, Low PS, Cushman M (2018) J Med Chem 61:10440–10462 Cywin CL, Zhao BP, McNeil DW, Hrapchak M, Prokopowicz AS, Goldberg DR, Morwick TM, Gao A, Jakes S, Kashem M, Magolda RL, Soll RM, Player MR, Bobko MA, Rinker J, DesJarlais RL, Winters MP (2003) Bioorg Med Chem Lett 13:1415–1418 Kaur M, Bahia MS, Silakari O (2012) J Chem Inf Model 52:2619–2630 Troiano V, Scarbaci K, Ettari R, Micale N, Cerchia C, Pinto A, Schirmeister T, Novellino E, Grasso S, Lavecchia A, Zappala M (2014) Eur J Med Chem 83:1–14 Bowling JJ, Pennaka HK, Ivey K, Wahyuono S, Kelly M, Schinazi RF, Valeriote FA, Graves DE, Hamann MT (2008) Chem Biol Drug Des 71:205–215 Kurtzberg LS, Roth S, Krumbholz R, Crawford J, Bormann C, Dunham S, Yao M, Rouleau C, Bagley RG, Yu XJ, Wang F, Schmid SM, LaVoie EJ, Teicher BA (2011) Clin Cancer Res 17:2777–2787 Barfacker L, Kuhl A, Hillisch A, Grosser R, Figueroa-Perez S, Heckroth H, Nitsche A, Erguden JK, Gielen-Haertwig H, Schlemmer KH, Mittendorf J, Paulsen H, Platzek J, Kolkhof P (2012) ChemMedChem 7:1385–1403 Mukhopadhyay C, Das P, Butcher RJ (2011) Org Lett 13:4664–4667 Nandi S, Islam MM, Saha M, Mitra S, Khatua S, Pal AK (2016) Synth Commun 46:1461–1476 Das P, Chaudhuri T, Mukhopadhyay C, Comb ACS (2014) Sci 16:606–613 Li C, Mu XY, Li YL, Liu Y, Wang XS (2013) ACS Comb Sci 15:267–272 Okuma K, Koga T, Ozaki S, Suzuki Y, Horigami K, Nagahora N, Shioji K, Fukuda M, Deshimaru M (2014) Chem Commun 50:15525–15528 Almansour AI, Kumar RS, Arumugam N, Basiri A, Kia Y, Ali MA (2015) Biomed Res Int 2015:1–9 Dimmock JR, Padmanilayam MP, Puthucode RN, Nazarali AJ, Motaganahalli NL, Zello GA, Quail JW, Oloo EO, Kraatz HB, Prisciak JS, Allen TM, Santos CL, Balzarini J, Clercq ED, Manavathu EK (2001) J Med Chem 44(4):586–593 Lavanya M, Thirumalai D, Asharani IV, Aravindan PG (2015) RSC Adv 5:86330–86336 Feng BB, Jin RZ, Zhang MM, Wang XS (2016) J Heterocyclic Chem 53:1578–1583 Bin Feng B, Zhang MM, Wang XS (2016) Polycycl Aromat Compd 36:478–489 Zhao Q, Yao CS, Wang XS (2018) Polycycl Aromat Compd 38:236–243 Dandia A, Parewa V, Gupta SL, Sharma A, Rathore KS, Jain A (2015) Catal Commun 61:88–91 Ray S, Das P, Banerjee B, Bhaumik A, Mukhopadhyay C (2015) ChemPlusChem 80:731–739 Wang HY, Shi JJ, Wang C, Zang XX, Wan Y, Wu H (2012) Dyes Pigm 95:268–274 Feng GL, Ji SJ, Lai WY, Huang W (2006) Synlett 17:2841–2845 Singh RM, Kumar R, Sharma N, Asthana M (2013) Tetrahedron 69:9443–9450 Singh JB, Chandra Bharadwaj K, Gupta T, Singh RM (2016) RSC Adv 6:26993–26999 Kumar R, Asthana M, Singh RM (2017) J Org Chem 82:11531–11542 Suneel Kumar Y, Nawaz Khan FR (2017b) Chin Chem Lett 28:1607–1612 Zeng LF, Wang Y, Kazemi R, Xu S, Xu ZL, Sanchez TW, Yang LM, Debnath B, Odde S, Xie H, Zheng Y-T, Ding J, Neamati N, Long Y-Q (2012) J Med Chem 55:9492–9509 Verma AK, Kotla SKR, Choudhary D, Patel M, Tiwari RK (2013) J Org Chem 78:4386–4401 Zahid M, Iaroshenko VO, Saghyan AS, Fischer C, Langer P (2013) Tetrahedron 69:3451–3458 Mishra K, Singh JB, Gupta T, Singh RM (2017) Org Chem Front 4:1794–1798 Muthukrishnan I, Vinoth P, Vivekanand T, Nagarajan S, Maheswari CU, Menendez JC, Sridharan V (2016) J Org Chem 81:1116–1124 Moustafa MS, Al-Mousawi SM, Elnagdi MH (2016) RSC Adv 6:90840–90845 Sadek KU, Selim MA, Alnajjar A-A, Atallah M, Elnagdi MH (2016) Eur J Chem 7:468–472 Al-Johani MA, Al-Zaydi KM, Mousally SM, Alqahtani NF, Elnagdi NH, Elnagdi MH (2017) Molecules 22:1–10 Yang F, Zheng L, Xiang J, Dang Q, Bai X (2010) J Comb Chem 12:476–481 Zhang Y, Zhu Y, Zheng L, Zhuo LG, Yang F, Dang Q, Yu ZX, Bai X (2014) Eur J Org Chem 2014:660–669 Jouha J, Buttard F, Lorion M, Berthonneau C, Khouili M, Hiebel MA, Guillaumet G, Briere JF, Suzenet F (2017) Org Lett 19:4770–4773 Dong W, Yuan Y, Gao X, Hu B, Xie X, Zhang Z (2018) ChemCatChem 10:2878–2886 Bagul SM, Birari DR, Ghagare MG, Toche RB, Jachak MN (2011) Monatsh Chem 142:169–175 Glaisyer EL, Watt MS, Booker-Milburn KI (2018) Org Lett 20:5877–5880 Wang DL, Shi XC, Wang YY, Ma J (2016) Chin Chem Lett 27:261–264 Tu MS, Li Y, Wang X, Jiang B, Wang SL, Tu SJ (2013) RSC Adv 3:3877–3880 Abdelrazek FM, Metwally NH, Kassab NA, Sobhy NA, Metz P, Jaegerb A (2010) J Heterocyclic Chem 47:384–388 Asthana M, Sharma N, Singh RM (2014) Tetrahedron 70:7996–8003 Ghoshal A, Yugandhar D, Nanubolu JB, Srivastava AK (2017) ACS Comb Sci 19:600–608 Metwally NH, Deeb EA (2018a) Synth Commun 48:1614–1628 Han ZG, Miao CB, Shi F, Ning M, Zhang G, Tu SJ (2010) J Comb Chem 12:16–19 Buksnaitiene R, Cikotiene I (2012) Heterocycl Commun 18:87–92 Bin Feng B, Lu L, Li C, Wang XS (2016) Org Biomol Chem 14:2774–2779 Okada E, Hatakenaka M, Kuratani M, Mori T, Ashida T (2014) Heterocycles 88:799–806 Muthukrishnan I, Vachan BS, Karuppasamy M, Eniyaval A, Uma Maheswari C, Nagarajan S, Menendez JC, Sridharan V (2019) Org Biomol Chem 17:6872–6879 Cailly T, Begtrup M (2010) Tetrahedron 66:1299–1307 Agarwal PK, Saifuddin M, Kundu B (2010) Tetrahedron 66:862–870 Meth-Cohn O, Narine B, Tarnowski B (1979) Tetrahedron Lett 20:3111–3114 Patin A, Belmont P (2005) Synthesis 14:2400–2406 Sharma N, Asthana M, Nandini D, Singh RP, Singh RM (2013) Tetrahedron 69:1822–1829 Wu JF, Liu MM, Huang SX, Wang Y (2015) Bioorg Med Chem Lett 25:3251–3255 Ramana PV, Prasad VK, Curie JR (2015) J Appl Chem 4:110–119 Bharath Kumar Reddy P, Ravi K, Mahesh K, Leelavathi P (2018) Tetrahedron Lett 59:4039–4043 Wortmann L, Lindenthal B, Muhn P, Walter A, Nubbemeyer R, Heldmann D, Sobek L, Morandi F, Schrey AK, Moosmayer D, Gunther J, Kuhnke J, Koppitz M, Lucking U, Rohn U, Schafer M, Reppel KN, Kuhne R, Weinmann H, Langer G (2019) J Med Chem 62:10321–10341 Fiorito J, Vendome J, Saeed F, Staniszewski A, Zhang H, Yan S, Deng SX, Arancio O, Landry DW (2017) J Med Chem 60:8858–8875 Buttard F, Berthonneau C, Hiebel MA, Briere JF, Suzenet F (2019) J Org Chem 84:3702–3714 Peese KM, Allard CW, Connolly T, Johnson BL, Li C, Patel M, Sorensen ME, Walker MA, Meanwell NA, McAuliffe B, Minassian B, Krystal M, Parker DD, Lewis HA, Kish K, Zhang P, Nolte RT, Simmermacher J, Jenkins S, Cianci C, Narasimhulu Naidu B (2019) J Med Chem 62:1348–1361 Wang MS, Zhuo LS, Yang FP, Wang WJ, Huang W, Yang GF (2020) Eur J Med Chem 185:1–13 Ganggjee A, Ohemeng KA (1987) J Heterocyclic Chem 24:123–126 Shen YC, Lin TT, Sheu JH, Duh CY (1999) J Nat Prod 62:1264–1267 Thompson AM, Connolly CJC, Hamby JM, Boushelle S, Hartl BG, Amar AM, Kraker AJ, Driscoll DL, Steinkampf RW, Patmore SJ, Vincent PW, Roberts BJ, Elliott WL, Klohs W, Leopold WR, Showalter HDH, Denny WA (2000) J Med Chem 43:4200–4211 Thompson AM, Rewcastle GW, Boushelle SL, Hartl BG, Kraker AJ, Lu GH, Batley BL, Panek RL, Hollis Showalter HD, Denny WA (2000) J Med Chem 43:3134–3147 Deady LW, Rodemann M, Zhuang L, Baguley BC, Denny WA (2003) J Med Chem 46:1049–1054 Deady LW, Rogers T, Zhuang L, Baguley BC, Denny WA (2005) Bioorg Med Chem 13:1341–1355 Deady LW, Rogers ML (2006) J Heterocyclic Chem 9:1–12 Ruchelman AL, Singh SK, Ray A, Wu XH, Yang JM, Li TK, Liu A, Liu LF, LaVoie EJ (2003) Bioorg Med Chem 11:2061–2073 Ruchelman AL, Kerrigan JE, Li TK, Zhou N, Liu A, Liu LF, LaVoie EJ (2004) Bioorg Med Chem 12:3731–3742 Ruchelman AL, Houghton PJ, Zhou N, Liu A, Liu LF, LaVoie EJ (2005) J Med Chem 48:792–804 Pettit GR, Hoffmann H, Herald DL, McNulty J, Murphy A, Higgs KC, Hamel E, Lewin NE, Pearce LV, Blumberg PM, Pettit RK, Knight JC (2004) J Org Chem 69:2251–2256 Pettit GR, Hoffmann H, McNulty J, Higgs KC, Murphy A, Molloy DJ, Herald DL, Williams MD, Pettit RK, Doubek DL, Hooper JNA, Albright L, Schmidt JM, Chapuis JC, Tackett LP (2004) J Nat Prod 67:506–509 Pettit GR, Hoffmann H, Herald DL, Blumberg PM, Hamel E, Schmidt JM, Chang Y, Pettit RK, Lewin NE, Pearce LV (2004) J Med Chem 47:1775–1782 Zhou Y, Beeler AB, Cho S, Wang Y, Franzblau SG, Snyder JK (2008) J Comb Chem 10:534–540 Bridewell DJA, Porter ACG, Finlay GJ, Baguley BC (2008) Cancer Chemother Pharmacol 62:753–762 Li Y, Liang J, Siu T, Hu E, Rossi MA, Barnett SF, Defeo-Jones D, Jones RE, Robinson RG, Leander K, Huber HE, Mittal S, Cosford N, Prasit P (2009) Bioorg Med Chem Lett 19:834–836 Sharma L, Tsai YC, Liu AA, Liu LF, LaVoie EJ (2009) Eur J Med Chem 44:1471–1476 Chen YY, Finlay GJ, Kirker JA, Marshall ES, Richardson E, Baguley BC (2011) Invest New Drugs 29:1504–1510 Desbois N, Pertuit D, Moretto J, Cachia C, Chauffert B, Bouyer F (2013) Eur J Med Chem 69:719–727 Insuasty B, Becerra D, Quiroga J, Abonia R, Nogueras M, Cobo J (2013) Eur J Med Chem 60:1–9 Prabha K, Prasad KJR (2013) Med Chem Comm 4:340–346 Dyshlovoy SA, Fedorov SN, Shubina LK, Kuzmich AS, Bokemeyer C, Keller-Von Amsberg G, Honecker F (2014) Biomed Res Int 2014:1–7 Murugesh AAM, Selvakumar M, Rajendran SP (2014) Int J Appl Biol Pharm 5:85–89 Mallinger A, Schiemann K, Rink C, Sejberg J, Honey MA, Czodrowski P, Stubbs M, Poeschke O, Busch M, Schneider R, Schwarz D, Musil D, Burke R, Urbahns K, Workman P, Wienke D, Clarke PA, Raynaud FI, Eccles SA, Esdar C, Rohdich F, Blagg J, Med ACS (2016) Chem Lett 7:573–578 Montoir D, Barille-Nion S, Tonnerre A, Juin P, Duflos M, Bazin MA (2016) Eur J Med Chem 119:17–33 Frasson I, Spano V, Di Martino S, Nadai M, Doria F, Parrino B, Carbone A, Cascioferro SM, Diana P, Cirrincione G, Freccero M, Barraja P, Richter SN, Montalbano A (2019) Eur J Med Chem 162:176–193 Xu G, Gao Y, Sun B, Peng L, Mao L, Jiang Y, Ding Q (2018) J Heterocycl Chem 55:2151–2156 Metwally NH, Deeb EA (2018b) Bioorg Chem 77:203–214 Liu C, Tang X, Li P, Li G (2012) Org Lett 14:1994–1997 Kallmeyer ST, Rubin JR, Humblet C, Hamby JM, Showalter HDH (1998) J Med Chem 41:1752–1763 Cushman M, Jayaraman M, Vroman JA, Fukunaga AK, Fox BM, Kohlhagen G, Strumberg D, Pommier Y (2000) J Med Chem 43:3688–3698 Utkina NK, Chaikina EL, Anisimov MM (2017) Nat Prod Commun 12:1437–1438 Pagar BP (2019) Asian J Chem 31:79–82 Khakwani S, Aslam S, Shahi MN, Mussadiq S, Benardino AMR, Khan MA (2017) Asian J Chem 29:27–30 Suresh T, Dhanabal T, Kumar RN, Mohan PS (2005) Ind J Chem 44B:2375–2379 Wadood FKA, Monem MIA, Fahmy AM, Geies AA (2008) Z Naturforsch 63:303–312 Sabatini S, Cecchetti V, Tabarrini O, Fravolini A (1999) J Heterocyclic Chem 36:953–957 Sanchez JP, Gogliotti RD (1993) J Heterocyclic Chem 30:855–859 Chan L, Jin H, Stefanac T, Lavallee JF, Falardeau G, Wang W, Bedard J, May S, Yuen L (1999) J Med Chem 42:3023–3025 Elslager EF, Tendick FH, Vi SA, Elslager EF, Tendick FH, Arbor A (1961) J Org Chem 5:546–558 Borne RF, Kim Fifer E, Waters IW (1984) J Med Chem 27:1271–1275 Vatsadze SZ, Kostochka ML, Lezina VP, Vinokurov VG, Klodt PM, Zyk NV (2005) Russ Chem Bull Int Ed 54:257–258 Makarem MS, Nasser AH, Mamdouh MA, Hanem MA, Megeid A, Farouk ME (2014) Der Pharma Chemica 6:394–410 Hinschberger A, Butt S, Lelong V, Boulouard M, Dumuis A, Dauphin F, Bureau R, Pfeiffer B, Renard P, Rault S (2003) J Med Chem 46:138–147 Sylvain R, Antoine H, Francois D, Michel B, Aline D (2001) WO 2001079205 A1 20011025 Thompson AM, Delaney AM, Hamby JM, Schroeder MC, Spoon TA, Crean SM, Showalter HDH, Denny WA (2005) J Med Chem 48:4628–4653 Wortmann L, Lindenthal B, Muhn P, Walter A, Nubbemeyer R, Heldmann D, Sobek L, Morandi F, Schrey AK, Moosmayer D, Gunther (2019) J Med Chem 62:10321–10341 Zhuang L, Wai JS, Embrey MW, Fisher TE, Egbertson MS, Payne LS, Guare JP, Vacca JP, Hazuda DJ, Felock PJ, Wolfe AL, Stillmock KA, Witmer MV, Moyer G, Schleif WA, Gabryelski LJ, Leonard YM, Lynch JJ, Michelson SR, Young SD (2003) J Med Chem 46:453–456 Peese KM, Allard CW, Connolly T, Johnson BL, Li C, Patel M, Sorensen ME, Walker MA, Meanwell NA, McAuliffe B, Minassian B (2019) J Med Chem 62:1348–1361 Clark RD, Repke DB, Berger J, Nelson JT, Kilpatrick AT, Brown CM, MacKinnon AC, Clague RU, Spedding M (1991) J Med Chem 34:705–717 Falardeau G, Lachance H, St-Pierre A, Yannopoulos CG, Drouin M, Bedard J, Chan L (2005) Bioorg Med Chem Lett 15:1693–1695 Bernardino A, Azevedo AR, Pinheiro LCS, Borges JC, Paixao ICP, Mesquita M, Souza TML, Dos Santos MS (2012) Org Med Chem Lett 2(3):1–7 Bernardino AM, Castro HC, Frugulhetti IC, Loureiro NI, Azevedo AR, Pinheiro LC, Souza TM, Giongo V, Passamani F, Magalhaes UO, Albuquerque MG (2008) Bioorg Med Chem 16:313–321 Gorecki DKJ, Hawes EM (1977) J Med Chem 20:124–128 Hawes EM, Gorecki DK, Johnson DD (1973) J Med Chem 16:849–853 Di Pietro O, Viayna E, Vicente-Garcia E, Bartolini M, Ramon R, Juarez-Jimenez J, Clos MV, Perez B, Andrisano V, Luque FJ, Lavilla R, Torrero DM (2014) Eur J Med Chem 73:141–152 Vanlaer S, Voet A, Gielens C, De Maeyer M, Compernolle F (2009) Eur J Org Chem 20:643–654 Di Pietro O, Perez-Areales FJ, Juarez-Jimenez J, Espargaro A, Clos MV, Perez B, Lavilla R, Sabate R, Luque FJ, Munoz-Torrero D (2014) Eur J Med Chem 84:107–117 Austin NE, Hadley MS, Harling JD, Harrington FP, Macdonald GJ, Mitchell DJ, Riley GJ, Stean TO, Stemp G, Stratton SC, Thompson M (2003) Bioorg Med Chem Lett 13:1627–1629 Cruz D, Wang Z, Kibbie J, Modlin R, Kwon O (2011) Proc Natl Acad Sci USA 108:6769–6774 Singh B, Bacon ER, Lesher GY, Robinson S, Pennock PO, Bode DC, Pagani ED, Bentley RG, Connell MJ, Hamel LT, Silver PJ (1995) J Med Chem 38:2546–2550 Wang HY, Shi JJ, Wang C, Zhang XX, Wan Y, Wu H (2012b) Dyes Pigm 95:268–274 Wang H, Shi J, Wang X, Zhang X, Zhao L, Wan Y, Wu H (2013) Spectrochem Acta A Mol Biomol Spect 103:62–67 Bauer U, Giordanetto F, Bauer M, Mahony GO, Johansson KE, Knecht W, Hartleib-Geschwindner J, Carlsson ET, Enroth C (2012) Bioorg Med Chem Lett 22:1944–1948 Sun B, Chen J, Ye F, Lu Y, Xu G, Mao L, Gao Y, Zhang H, Wang H, Peng L (2019) ChemistrySelect 4:6552–6556 Li H, Sun W, Huang X, Lu X, Patel PR, Kim M, Orr MJ, Fisher RM, Tanaka TQ, Mckew JC, Simeonov A, Sanderson PE, Zheng W, Williamson KC, Huang W (2017) ACS Comb Sci 19:748–754