Supporting Information-B. A Facile Iterative Synthesis of 2,5-Terpyrimidinylenes as Non-peptidic α-helical Mimics
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1 Supporting Information-B A Facile Iterative Synthesis of 2,5-Terpyrimidinylenes as on-peptidic α-helical Mimics Laura Anderson, 1,2 Mingzhou Zhou, 1,2 Vasudha Sharma, 2 Jillian M. McLaughlin, 2 Daniel. Santiago, 1 Frank R. Fronczek, 3 Wayne C. Guida, 1,2 and Mark L. McLaughlin 1,2, * 1 Department of Chemistry, University of South Florida, 422 E. Fowler Ave, Tampa, Florida 3362, 2 Department of Drug Discovery, H. Lee Moffitt Cancer Center, 1292 Magnolia Dr, Tampa, Florida 33612, and 3 Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 78 1 H & 13 C Spectra of Compounds: 2a f. S2 3a j. S S S S39 S1
2 5-Methyl-3-oxohexanenitrile (2a) C C S2
3 3-xo-4-phenylbutanenitrile (2b) C C S3
4 S4 5-Cyclohexyl-3-oxo pentanenitrile(2d) C C
5 S5 Methyl 2-(naphthalen-2-yl)acetate Me Me
6 4-(aphthalen-1-yl)-3-oxobutanenitrile (2e) C C S6
7 4-(aphthalen-2-yl)-3-oxobutanenitrile (2f) C C S7
8 (E/Z)-2-((Dimethylamino)methylene)-5-methyl-3-oxohexanenitrile (3a) C C S8
9 (E/Z)-2-((Dimethylamino)methylene)-3-oxo-4-phenylbutanenitrile (3b) C C S9
10 (E/Z)-2-((Dimethylamino)methylene)-4-methyl-3-oxopentanenitrile (3c) C C S1
11 S11 (E/Z)-5-Cyclohexyl-2-((dimethylamino)methylene)-3-oxopentanenitrile (3d) C Me 2 C Me 2
12 (E/Z)-2-((Dimethylamino)methylene)-4-(naphthalen-1-yl)-3-oxobutanenitrile (3e) C C S12
13 (E/Z)-2-((Dimethylamino)methylene)-4-(naphthalen-2-yl)-3-oxobutanenitrile (3f) C C S13
14 (E/Z)-2-((Dimethylamino)methylene)-3-oxobutanenitrile (3g) C Me 2 C Me S14
15 (E/Z)-2-((Dimethylamino)methylene)-4,4-dimethyl-3-oxopentanenitrile (3i) C C S15
16 (E/Z)-2-Benzoyl-3-(dimethylamino)acrylonitrile (3j) C C S16
17 2-Amino-4-benzylpyrimidine-5-carbonitrile (4-1) H 2 C H 2 C S17
18 4-Benzylpyrimidine-5-carbonitrile (4-2) C C S18
19 4-Benzyl-2-methylpyrimidine-5-carbonitrile (4-3) C C S19
20 4-Benzyl-2-phenylpyrimidine-5-carbonitrile (4-4) C C S2
21 S21 4-Isobutyl-2-phenylpyrimidine-5-carbonitrile (4-5) C C
22 2-Amino-4-isobutylpyrimidine-5-carbonitrile (4-6) H 2 C H 2 C S22
23 S23 4-Isopropyl-2-methylpyrimidine-5-carbonitrile (4-7) C C
24 4-Isopropyl-2-phenylpyrimidine-5-carbonitrile (4-8) C C S24
25 2-Amino-4-isopropylpyrimidine-5-carbonitrile (4-9) H 2 C H 2 C S25
26 4-(2-Cyclohexylethyl)-2-methylpyrimidine-5-carbonitrile (4-1) C C S26
27 4-(2-Cyclohexylethyl)-2-phenylpyrimidine-5-carbonitrile (4-11) C C S27
28 4-tert-Butyl-2-phenylpyrimidine-5-carbonitrile (4-12) C C S28
29 2-Amino-4-tert-butylpyrimidine-5-carbonitrile (4-13) H 2 C H 2 C S29
30 4,4'-Diisobutyl-2'-phenyl-2,5'-bipyrimidine-5-carbonitrile (5-1) C C S3
31 4-Benzyl-4'-isobutyl-2'-phenyl-2,5'-bipyrimidine-5-carbonitrile (5-2) C C S31
32 S32 4'-Benzyl-4-(naphthalen-2-ylmethyl)-2'-phenyl-2,5'-bipyrimidine-5-carbonitrile (5-3) C C
33 S33 4'-Benzyl-4-methyl-2'-phenyl-2,5'-bipyrimidine-5-carbonitrile (5-4) C C
34 2'-Amino-4-benzyl-4'-isobutyl-2,5'-bipyrimidine-5-carbonitrile (5-5) H 2 C H 2 C S34
35 S35 4'-Benzyl-4-isobutyl-2'-phenyl-2,5'-bipyrimidine-5-carbonitrile (5-6): C C
36 4'-Benzyl-4-(naphthalen-1-ylmethyl)-2'-phenyl-2,5'-bipyrimidine-5-carbonitrile (5-7): C C S36
37 Crystal data C33H235 F = 124 Mr = Dx = Mg m 3 Monoclinic, P21/n Mo Kα radiation λ =.7173 Å Hall symbol: -P 2yn Cell parameters from 538 reflections a = (15) Å θ = º b = (3) Å µ =.8 mm 1 c = (16) Å T = 9. (5) K β = (9)º Plate fragment,? V = (6) Å mm Z = 4 Data collection KappaCCD (with xford Cryostream) diffractometer 3888 reflections with I > 2σ(I) Radiation source: fine-focus sealed tube Rint =.27 Monochromator: graphite θmax = 27.1º T = 9.(5) K θmin = 2.6º ω and φ scans h = S37
38 Absorption correction: none k = measured reflections l = independent reflections Refinement Refinement on F2 Secondary atom site location: difference Fourier map Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites R[F2 > 2σ(F2)] =.47 H-atom parameters constrained wr(f2) =.11 w = 1/[σ2(Fo 2) + (.427P) P] where P = (Fo 2 + 2Fc 2)/3 S = 1.7 ( /σ)max < reflections ρmax =.22 e Å parameters ρmin =.2 e Å 3 32 restraints Extinction correction: SHELXL, Fc*=kFc[1+.1xFc2λ3/sin(2θ)]-1/4 S38
39 5 -Cyano-4 -isopropyl-4 -phenylmethyl-4-isobutyl-2-phenylterpyrimidine (6-1) C C S39
40 S4 5 -Cyano-4,4 -diisobutyl-4 -(2-naphthylmethyl)-2-phenylterpyrimidine (6-2) C C
41 5 -Cyano-4,4 -diisobutyl-4 -(2-phenylmethyl)-2-phenylterpyrimidine (6-3) C C S41
42 5 -Cyano-4,4 -diisobutyl-4 -(1-naphthylmethyl)-2-phenylterpyrimidine(6-4) C C S42
43 S43 5 -Cyano-4 -isobutyl-4 -(1-naphthylmethyl)-4-(2-phenylmethyl)-2-phenylterpyrimidine(6-5) C C
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