Practical Synthesis of PC190723, an Inhibitor of the Bacterial Cell Division Protein FtsZ!
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1 Practical ynthesis of PC190723, an Inhibitor of the Bacterial Cell Division Protein tsz! orto,. A.; lmstead, M. M.; haw, J. T. J. rg. Chem. 2010, 75, 7946.! Ammonia ynthons for the Multicomponent Assembly of Complex γ-lactams" Tan, D. Q.; Martin, K..; ettinger, J. C.; haw, J. T. Proc. at. Acad. ci. 2011, 108, 6781.!
2 Jared haw! Education! 1993 B.. UC Berkeley with ayton eathcock! 1999 D UC Irvine with Keith Woerpel! Professional Career! I Postdoctoral ellow with David Evans! arvard dical chool Institute ellow at Institute of Chemistry and Cell Biology! Broad Institute Institute ellow in the Chemical Biology Program! 2007-present UC Davis Assistant Professor!
3 tsz! Current Problem: Pathogenic bacteria resistant to current an+bio+cs requires new methods for trea+ng infec+on. Promising area of research lies in inhibi+on of cell division. tsz: Protein that ini+ates bacterial cell division. Prokaryo+c version of tubulin. ew selec+ve inhibitors of tsz are known. o direct elucida+on of the binding site(s) for tsz inhibitors. Vollmer, W. Chem. Biol. 2008, 15, 93.
4 Discovery of PC190723! 3- methoxybenzamide: - Many inhibitors of tsz were not potent enough for clinical trials. - 3MBA showed weak inhibi+on, but high selec+vity analogues were developed and screened with one hit. PC190723: - In mice, dose of 30mg/kg saved 100% of mice infected with taphylococcus aureus. tokes,. R.; et. al. cience, 2008, 321, 1673.
5 Ac+ve program to synthesize tsz inhibitors: tsz and Jared haw! (±)-dichamanetin and (±)-2 -hydroxy-5 -benzylisouvarinol-b Urgaonkar,.; La Pierre,..; ir, I.; Lund,.; RayChaudhury, D.; haw, J. T. rg. Lett. 2005, 7, (+)-totarol (-)-viriditoxin i-pr C 2 C 2 Kim, M.B.; haw, J. T. rg. Lett. 2010, 12, Park, Y..; Grove, C. I.; Gonzalez-Lopez, M.; Urgaonkar,.; ettinger, J. C.; haw, J. T. Angew. Chem., Int. Ed. 2011, 50, 3730.
6 hawʼs Approach to PC190723! Retrosynthe+c Analysis: + R R=,, $13/mmol $182/mol pyridine can be made through reduction of nitro derivative ($2.77/mmol)
7 orward ynthesis! Et EM n-buli EM Li DIPEA C % 1. C 2 Et DIPEA aq. 4 C 2 93% 1. DM 2. 52% (2 steps) 2. 89% (2 steps), 2 4 EM 99%
8 x orward ynthesis! 94% Lawesson's reagent p-xylene, 110 C 65% C, C 4 x Lawesson's reagent 110 C, 12 h DCM 67% Lawesson's reagent toluene, 110 C 75% ai, K 2 C 3 0% 66%
9 Completion and utlook! Cs 2 C 3, C mixture of products
10 Completion and utlook! Cs 2 C 3 62% 4 x PC190723
11 Completion and utlook! Cs 2 C 3 40% PC Alternative Route: ai, T 78% I K 2 C 3 70% PC or 9 total steps (5-6 linear) from commercially available materials Produces access to significant quantities of PC or derivatives for development of new tsz inhibitors. amples available on request (shaw@chem.ucdavis.edu)
12 elected γ-lactam Compounds! lactacystin heliotropamide 2 C Ac UCB-2892 salinosporamide A γ-lactams are prevalent in nature and are present in medicinal leads and approved drugs.! - lactams are twice as prevalent as -substituted lactams.! thods to efficiently synthesize - lactams is limited = gap in knowledge.
13 thods to ynthesize - Lactams! 2 3 i P() 2 1. LDA T 2. TBA 2 P() 2 74%, >20:1 dr 3M /T µw 98%, >20:1 dr Lettan II, R. B.; Galliford, C. V.; Woodward, C. C.; cheidt, K. A. J. Am. Chem. oc. 2009, 131, Ar CR R 1 B 4 Et Et (5 mol %) Mg(t-Bu) 2 (5 mol %) TBD T, 60 C, 24 h Ar RC R 1 20 examples 61-85% yield 85-98% ee 5-20:1 dr 2 Raney i 40 C 92% Et 2 C Raup, D. E. A.; Cardinal-David, B.; olte, D.; cheidt, K. A. ature Chem. 2010, 2, 766.
14 Discovery of 4-Component Assembly! R 1 R 2 R 3 1. toluene, reflux 2. K 2 C 3 /C 3 I R 1 R 3 R 2 12 examples 63-93% yield Wei, J.; haw, J. T. rg. Lett. 2007, 9, 4077.
15 Discovery of 4-Component Assembly! R 1 R 1 R 3 R 2 R 1 R 2 R 3 R 1 R 3 R 1 R 3 R2 C 2 R 1 R 2 R 3 R 3 R 1 R 3 R 2 C 2 R 1 R 2 R 3 R 2 R 1 R 3 Wei, J.; haw, J. T. rg. Lett. 2007, 9, 4077.
16 Extension to eliotropamide! i-pr i-pr 1. toluene, reflux 2. K 2 C 3 /C 3 I 76% (2 steps) i-pr i-pr i-pr 1. LDA (2.2 equiv) 2. C 2 3. B 3 i-pr 1. TM 3 i, AIB (90%) 2. a, (97%) 3. R, EDCI, Et 3 DMAP (88%) 81% (3 steps) (±)-heliotropamide i-pr Younai, A.; Chin, G..; haw, J. T. J. rg. Chem. 2010, 75, 8333.
17 thod Extension to - Lactams! R 2 R 3 " 3 " 1. toluene, reflux 2. K 2 C 3 /C 3 I R 3 R 2 cond's R R 3 R 2
18 thod Extension to - Lactams! " 3 " 1. toluene, reflux 2. K 2 C 3 /C 3 I p-tol entry ammonia source conditions yield (%) 1 4 (aq), 145 C, 22 h (aq), 150 C, 3 h Ac, 150 C, 0.5 h Ac, 150 C, 1 h Ac, 150 C, 3 h C 3 C 2, 150 C, 1 h (g), 145 C, 22 h 14
19 thod Extension to - Lactams! " 3 " 1. toluene, reflux 2. K 2 C 3 /C 3 I p-tol entry ammonia source conditions yield (%) 1 4 (aq), 145 C, 22 h (aq), 150 C, 3 h Ac, 150 C, 0.5 h Ac, 150 C, 1 h 32 p-tol C 2 R=C 3 : 24%, 4.5:1 dr =: 59%, 3:1 dr =Br: 45%, 3:1 dr p-tol C 2 C 2 C 2 R 37%, 2.4:1 dr 34%, 3:1 dr 44%, 3:1 dr
20 Two-step Protocol! R 1. toluene, reflux R conditions 2. K 2 C 3 /C 3 I p-tol p-tol p- A p- B X Y R low deprotection yields amine 4-component reaction deprotection A 77% yield, 4:1 dr TA, reflux; 91% yield B 52% yield, 9:1 dr Rh 3 (2 mol %), then Ac; 65% yield
21 -unctionalization! n-buli, RX R RB() 2 (4 equiv) Cu(Ac) 2 (2 equiv) R p-tol C 2 T -78 to 23 C p-tol C 2 p-tol C 2 Et 3 (4 equiv), C 3Å M 23 C, 48 h p-tol C 2 Et p-tol p-tol C 2 C 2 57% 58% p-tol p-tol C 2 C 2 84% 56% p-tol p-tol C 2 P 25% 42% p-tol C 2 32% p-tol C 2 0% p-tol C 2
22 The uture of haw! Continue the syntheses of tsz inhibitors with efforts to discover potent drug leads. Discover and apply new multicomponent reactions for rapid access to complex molecules. tudy bacterial cell division inhibitors that do not interfere with tsz (i.e. 5346) and probe the mechanism of action through target ID studies. A future highly motivated graduate student i-pr
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