No Title. Li HUANG August 07, 2008
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1 o Title Li UAG August 07, 2008
2 utline Bioisostere and Isostere Report on the possibility of thioureas catalyzed Claisen rearrangement
3 Isosteres are DefiniIon of isostere molecules or ions with the same number of atoms and the same number of valence electrons. As a result, they can exhibit similar pharmacokine<c and pharmacodynamic proper<es S S
4 Bioisostere Friedman (1951):Bioisosteres are atoms or molecules that fit the broadest definiion for isosteres and have the same type of biological acivity. Thornber(1979): Groups or molecules which have chemical and physical similariies producing broadly similar biological effects. Why? Greater selecivity Less side effects Decreased toxicity Improved pharmacokineics (solubility hydrophobicity) Increased stability Simplified synthesis Patented lead compounds
5 Classes of Bioisosteres Classical bioisosteres onclassical bioisosteres
6 Classical bioisosteres
7 Classical bioisosteres to F replacement R E-S R S E methylene-tf R C 2 TF S E 2'-deoxyuridylic R F E-S R F S E methylene-tf R F C 2 TF S E R Thymidylate (DA synthesis) 5-fluorouracil (antineoplastic) - 3 P E-S: Thymidate synthase methylene-tf: 5,10-methylenetetrahydrofolic acid R =
8 Classical bioisosteres
9 Classical bioisosteres X Van der Waals radius (A) IC 50 (nm) Me 2 C C 2 Et X Me S
10 onclassical bioisosteres Cyclic vs oncyclic replacement F R F R R S C S C Minimum inhibitory concentration (MIC) (ug/ml) Gram positive bacteria Gram negative bacteria Balsamo, A.; Broccali, G.; Lapucci, A.; Maxxhia, B.; Macchia, F.; rlandini, S.; Rossello, A. J. Med. Chem. 1989, 32, 1398.
11 Isosteres in catalyst design A Brønsted Acid Catalyst for the Enan<oselec<ve Protona<on Reac<on Cheon, C..; Yamamoto,. J. Am. Chem. Soc. 2008, 130, 9246.
12 Catalyst design X X Tf pka of A > pka of B A B X = RC, RS= Tf pka(c 3 C) P P Tf Ar P Tf Ar Ar = 1,3,5-(i-Pr) 3 C 6 2 akashima, D.; Yamamoto,. J. Am. Chem. Soc. 2006, 128, 9626.
13 ReacIvity of the catalysts Et + Chiral Bronsted Acid (5 mol%) - 78 o C CEt (endo/exo = >98/<2) P (1.2 equiv.) 1 chiral bronsted acid Solvent Time (h) Yield ee(%) 1 C 2 Cl n.d. P Tf 2 C 2 Cl (S) 2 Ar 3 C 2 Cl (R) P Tf Ar 3 Ar = 1,3,5-(i-Pr) 3 C 6 2 akashima, D.; Yamamoto,. J. Am. Chem. Soc. 2006, 128, 9626.
14 ReacIvity of the catalysts Et TIPS Chiral Bronsted Acid (5 mol%) CEt + (endo/exo = >98/<2) - 78 o C TIPS (1.5 equiv.) P chiral bronsted acid Solvent Time (h) Yield ee(%) Toluene Toluene Toluene <10 95 n.d. n.d P Tf Ar 2 RTIPS 3 P Tf silylated catalysts (inactive) Ar 3 Ar = 1,3,5-(i-Pr) 3 C 6 2 akashima, D.; Yamamoto,. J. Am. Chem. Soc. 2006, 128, 9626.
15 Isostere in catalyst design S 2 Me S Se pka (DMS) a Ar X P Y Ar X Ar = 1,3,5-(i-Pr) 3 C 6 2 Y 3b S 3c Tf 3d 3e S Se Tf Tf
16 Catalyst reacivity TMS catalyst (10 mol%) * 2,4,6-(C 3 ) 3 C 6 2 C toluene, rt Ar P X Y Ar = 1,3,5-(i-Pr) 3 C 6 2 Ar X Y time (h) Yield (%) er 3a 96 R D 3b S 96 trace D 3c Tf 4.5 >99(98) 77:23 3d S Tf 3.5 >99(97) 89:11 3e Se Tf 3.5 >99(97) 86:14
17 Mechanism for protonaion reacion A + [ 2 ] + [A] - TMS R [ 2 ] + [A] - TMS R R or A TMS
18 PossibiliIes on thioureas catalyzed Claisen rearrangement Claisen rearrangement was accelerated by proic solvents or Bronsted Acids. X X Kristen, M.; Rehbein, J.; iersemann, M.; Strassner, T. J. rg. Chem. 2007, 72, Severance, D. L.; Jorgensen, W. L. J. Am. Chem. Soc. 1992, 114,
19 Rate acceleraion of Claisen rearrangement 4 (E) 1a 100 o C C 6 D 6 5 equiv (1a) k rel CF 3 CF 3 none X C C C 2 C a X = 1b X = S Curran, D. P.; Kuo, L.. Tetrahedron Le>. 1995, 36(37), 6647.
20 Rate acceleraion of Claisen rearrangement 1a 2 or 3 Me 4 (E/Z 2.6:1) 80 o C C 6 D 6 Me 5 Me 4 (E/Z 2.6:1) 80 o C C 6 D 6 Me 5 equiv (1a) k rel equiv k rel none 1 none (1.0 equiv.) (1.0 equiv.) DMS (5.0 equiv.) 1.9 CF 3 CF 3 X C C C 2 C a X = 1b X = S C C C 2 C 8 17 C 3 C 3 Curran, D. P.; Kuo, L.. Tetrahedron Le>. 1995, 36(37), CF 3 2 X CF 3 C C CF 3 3
21 Bis hydrogen bonded model Ar Ar Ar Ar Me Me Thiourea has weaker acceleraing effect than urea ydrogen bonding is crucial instead of acidity
22 Claisen rearrangement catalyzed by thiourea S C 2 -i-pr R 1 3 R 2 C 2 -i-pr 1 2 entry thiourea mol% solvent T ( o C) Ime Conv. (%) CCl d CF 3 C d CF 3 C h DCE 25 5 d 14 5 CCl d 10 6 CF 3 C d 41 7 CF 3 C h 41 8 DCE 25 5 d 7 Kristen, M.; Rehbein, J.; iersemann, M.; Strassner, T. J. rg. Chem. 2007, 72,
23 Claisen rearrangement catalyzed by thiourea C 2 -i-pr Ar = 2,5-(CF 3 )-C 6 3 Ar S 3 Ar CCl 3, 45 o C sealed test tube 1 2 C 2 -i-pr Conversion (%) entry t (d) 100 mol% 3 no
24 Conclusion Thioureas are ineffecive as catalysts for the Claisen rearrangement of 2 alkoxylcarbonyl subsituted allyl vinyl ethers. It is important to have a suitable catalyst/substrate combinaion. The transiion model proposed is useful in catalyst design.
25 Bis(hydrogen) bond binding models of thiourea catalysts S S A B C S Kleiner, C. M.; Schreiner, P. R. Chem. Commun., 2006, 4315.
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33 ReacIvity of Imine C C 2.3 D 0.9 D Ahaching acivaing groups on the imine Me S P C
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