Discovery of Type II inhibitors of TGF-beta-activated kinase 1 (TAK1) and Mitogen-activated. protein kinase kinase kinase kinase 2 (MAP4K2)
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- Ὑάκινθος Βασιλόπουλος
- 5 χρόνια πριν
- Προβολές:
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1 Discovery of Type II inhibitors of TGF-beta-activated kinase 1 (TAK1) and Mitogen-activated protein kinase kinase kinase kinase 2 (MAP4K2) Supplemental Information Li Tan 1,2, Tyzoon omanbhoy 3, Deepak Gurbani 4, Matthew Patricelli 3, John Hunter 4, Jiefei Geng 5, Lina Herhaus 6, Jianming Zhang 1,2, Eduardo Pauls 6, Youngjin Ham 1,2, Hwan Geun Choi 1, Ting Xie 1,2, Xianming Deng 1,2, Sara J. Buhrlage 1, Taebo Sim 7, Philip Cohen 6, Gopal Sapkota 6, Kenneth D. Westover 4, athanael S. Gray 1,2 * 1. Dana Farber Cancer Institute, Harvard Medical School, Boston, MA, 02115, USA 2. Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, Boston, Massachusetts, 02115, USA 3. ActivX Biosciences, La Jolla, CA 92037, USA 4. Departments of Biochemistry and Radiation ncology, The University of Texas, Southwestern Medical Center, 5323 Harry Hines Blvd., Dallas, TX 75390, USA 5. Department of Cell Biology, Harvard Medical School, Boston, Massachusetts, 02115, USA 6. MRC Protein Phosphorylation and Ubiquitylation Unit, College of Life Sciences, University of Dundee, Dow Street, Dundee DD1 5EH, UK 7. Chemical Kinomics Research Center, Korea Institute of Science and Technology, 39-1, Hawolgok-dong, Seongbuk-gu, Seoul, , Korea *Correspondence: nathanael_gray@dfci.harvard.edu (SG) Contents: Figure S1-S6 (page S2-S4); Table S1-S4 (page S5-S6); Structures and spectral data of compounds 3-26 (page S7-17). S1
2 Figure S1. Kinases profiling data of 1 at 100 nm. Lower score means higher inhibition. S2
3 Figure S2. X-ray structure of 1 in complex with TAK1. A) The compound structure is superimposed on a Fo-Fc difference map contoured at 2.5σ (grey mesh). The map was calculated using initial phases after molecular replacement without including 1 in the model to avoid bias. B) Schematic overview of interactions between the TAK1 active site and 1. Hydrogen bonds are depicted by dashes and hydrophobic interactions by green contours. Figure S3. L929 cells were pre-treated with: A) indicated TAK1 (37), TAK1/MAP4K2 (1), selective MAP4K2 (12, 16, 17) and p38 inhibitors (38) at the concentration of 1 µm for 30 min; B) 1 at 0.1 µm and selective p38 inhibitor 39 at 0.1 and 1.0 µm and then TFα was added and incubated for 5 min. Samples were collected and subjected to Western blot. S3
4 Figure S4. Structure of S1. H S1 H CF 3 Figure S5. Wild type and TAK1-null MEF cells were pre-treated with 1 (A, B) or 37 (C) for 1 hour, then stimulated with TGFß (A, C) or IL 1α (B, C). Samples were collected and subjected to Western blot. Figure S6. Structrues of H 37 H H F H 38 S F F Br 39 H S4
5 Table S1. Crystallographic data and structure statistics TAK1-1 complex Wavelength (Å) Space Group I222 Unit cell dimension (Å) 58.2, 132.9, Resolution (Å) ( ) Unique Reflections 22,388 Completeness (%) 98.6 (95.7) Redundancy 7.0 (6.3) R merge (%) 8.2 (93.1) I/sigma 16.1 (2.2) Wilson B-factor (Å 2 ) R cryst /R free 20.3 / 22.5 PDB accession 491 Table S2. SAR for p38α. ID Kiativ* Emzymatic Inhibition (%) IC50 (nm) * 1 and 2 were profiled at 0.5 µm on A375 live cell while all others were at 1.0 µm on HUH7 lysate. S5
6 Table S3. SAR for ABL. Kiativ* Ba/F3 ID Inhibition (% ) IC50 (um) Lys1 ACT Parental Bcr/Abl > >90 > > > > > > > > > > > > * 1 and 2 were profiled at 0.5 µm on A375 live cell while all others were at 1.0 µm on HUH7 lysate. Table S4. SAR for other kinases. ID Kiativ* Inhibition (%) Enzymatic IC50 (nm) ZAK CS K EPHA2 FES FER ZAK CS K EPHA2 FES FER > * 1 and 2 were profiled at 0.5 um on A375 live cell while all others were at 1.0 µm on HUH7 lysate. S6
7 3-((7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)--(4-((4-ethylpiperazin-1- yl)methyl)-3- (trifluoromethyl)phenyl)-4-methylbenzamide (3). 1 H MR (400 MHz, DMS) δ (bs, 1H), (s,1h), 8.26 (s, 1H), 8.15 (s, 1H), 8.03 (d, J = 8.8 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.82 (s, 1H), 7.66 (d, J = 8.8 Hz, 1H), 7.51 (d, J = 8.0 Hz, 1H), 7.48 (dd, J = 3.6, 2.4, 1H), 6.53 (dd, J = 3.6, 2.0, 1H), 3.57 (s, 2H), (m, 8H), 2.47 (q, J = 7.2 Hz, 2H), 2.14 (s, 3H), 1.04 (t, J = 7.2 Hz, 3H). MS (ESI) m/z 539 (M+H) +. 3-((1H-pyrazolo[3,4-d]pyrimidin-4-yl)oxy)--(4-((4-ethylpiperazin-1-yl)methyl)-3- (trifluoromethyl)phenyl)-4-methylbenzamide (4). 1 H MR (400 MHz, DMS) δ (s,1h), 8.49 (s, 1H), 8.23 (s, 1H), 8.15 (d, J = 2.0 Hz, 1H), 8.01 (dd, J = 8.4, 2.0 Hz, 1H), 7.90 (d, J = 8.0 Hz, 1H), 7.88 (s, 1H), 7.68 (d, J = 8.8 Hz, 1H), 7.55 (d, J = 8.0, 1H), 3.54 (s, 2H), (m, 8H), 2.33 (q, J = 6.8 Hz, 2H), 2.17 (s, 3H), 0.96 (t, J = 6.8 Hz, 3H). 13 C MR (100 MHz, DMS) δ , , , , , , , , , , , , , , , , , , 57.88, 53.23, 52.80, 52.00, 16.39, MS (ESI) m/z 540 (M+H) +. S7
8 -(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methyl-3-((6-methyl-7Hpyrrolo[2,3-d]pyrimidin-4-yl)oxy)benzamide (5). 1 H MR (400 MHz, DMS) δ 12.09(bs, 1H), (s,1h), 8.20 (s, 1H), 8.18 (s, 1H), 8.03 (d, J = 8.0 Hz, 1H), 7.87 (d, J = 7.6 Hz, 1H), 7.82 (s, 1H), 7.69 (d, J = 8.8 Hz, 1H), 7.52 (d, J = 8.4, 1H), 6.22 (s,1h), 3.55 (s, 2H), (m, 8H), 2.41 (s, 3H), 2.30 (q, J = 7.2 Hz, 2H), 2.15 (s, 3H), 0.97 (t, J = 7.2 Hz, 3H). 13 C MR (100 MHz, DMS) δ , , , , , , , , , , , , , , , , , , 95.40, 57.90, 53.27, 52.82, 52.02, 16.48, 13.78, MS (ESI) m/z 553 (M+H) +. -(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methyl-3-((6- (methylamino)pyrimidin-4-yl)oxy)benzamide (6). 1 H MR (400 MHz, DMS) δ (s,1h), 8.11 (s, 1H), 8.00 (d, J = 8.4 Hz, 1H), 7.75 (d, J = 8.0 Hz, 1H), 7.64 (s, 1H), 7.62 (d, J = 8.8 Hz, 1H), 7.41 (d, J = 8.0, 1H), 7.33 (bs, 1H), 3.60 (s, 2H), 3.38 (m, 2H), (m, 6H), 2.71 (bs, 3H), (m, 2H), 2.09 (s, 3H), 1.12 (t, J = 6.8 Hz, 3H). MS (ESI) m/z 529 (M+H) +. S8
9 -(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methyl-3-((2- (methylamino)pyrimidin-4-yl)oxy)benzamide (7). 1 H MR (400 MHz, DMS) δ (s,1h), 8.18 (bs, 1H), 8.16 (s, 1H), 8.02 (d, J = 8.4 Hz, 1H), 7.81 (d, J = 8.0 Hz, 1H), 7.75 (s, 1H), 7.68 (d, J = 8.4 Hz, 1H), 7.48 (d, J = 8.4, 1H), 3.54 (s, 2H), (m, 2H), 2.52 (s, 3H), (m, 4H), 2.28 (q, J = 7.2, 2H), 2.16 (s, 3H), 0.96 (t, J = 7.2 Hz, 3H). MS (ESI) m/z 529 (M+H) +. 3-((6,7-dimethoxyquinazolin-4-yl)oxy)--(4-((4-ethylpiperazin-1-yl)methyl)-3- (trifluoromethyl)phenyl)-4-methylbenzamide (8). 1 H MR (400 MHz, DMS) δ (s,1h), 8.18 (d, J = 9.2 Hz, 1H), 8.06 (d, J = 5.6 Hz, 1H), 7.88 (s, 1H), 7.68 (d, J = 5.6 Hz, 1H), 7.41 (d, J = 8.8, 1H), 7.34 (s, 1H), 7.17 (s, 1H), 7.09 (s, 1H), 7.00 (s, 1H), 3.98 (s, 3H), 3.86 (s, 3H), 3.65 (s, 2H), 3.43 (m, 2H), 3.12(m, 2H), (m, 4H), 2.36 (q, J = 7.2, 2H), 2.17 (s, 3H), 1.19 (t, J = 7.2 Hz, 3H). MS (ESI) m/z 610 (M+H) +. S9
10 4-(5-((4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)carbamoyl)-2- methylphenoxy)--methylpicolinamide (9). 1 H MR (600 MHz, DMS) δ (s,1h), 8.77 (m, 1H), 8.53 (d, J = 5.6 Hz, 1H), 8.16 (s, 1H), 8.06 (d, J = 8.4 Hz, 1H), 7.91 (d, J = 8.0 Hz, 1H), 7.78 (s,1h), 7.69 (d, J = 8.4 Hz, 1H), 7.60 (d, J = 8.4, 1H), 7.31(s, 1H), 7.15 (d, J = 5.6 Hz, 1H), 3.65 (s, 2H), 3.43 (m, 2H), 3.12(m, 2H), (m, 4H), 2.76 (d, J = 4.8 Hz, 3H), 2.35 (q, J = 7.2, 2H), 2.18 (s, 3H), 1.18 (t, J = 7.2 Hz, 3H). MS (ESI) m/z 556 (M+H) +. 3-((1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)--(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide (10). 1 H MR (400 MHz, DMS) δ (bs, 1H), (s, 1H), 8.19(s, 1H), 8.13 (d, J = 5.6 Hz, 1H), 8.02 (dd, J = 8.4, 1.6 Hz, 1H), 7.89 (d, J = 8.0 Hz, 1H), 7.80 (m,1h), 7.70 (d, J = 8.8 Hz, 1H), 7.64 (dd, J = 8.0,7.6 Hz, 1H), 7.38 (dd, J = 8.0, 2.4, 1H), 7.39 (m, 1H), 6.52 (d, J = 5.6, 1H), 6.21 (m, 1H), 3.57 (s, 2H), (m, 10H), 2.24 (s, 3H), 1.01 (t, J = 7.2 Hz, 3H). MS (ESI) m/z 524 (M+H) +. S10
11 -(3-((1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)-4-methylphenyl)-4-((4-ethylpiperazin-1-yl)methyl)- 3-(trifluoromethyl)benzamide (11). 1 H MR (600 MHz, DMS) δ (bs, 1H), (s,1h), 8.20 (s, 1H), 8.18 (d, J = 8.0 Hz, 1H), 8.08 (d, J = 5.6 Hz, 1H), 7.90 (d, J = 8.0 Hz, 1H), 7.63 (d, J = 8.0 Hz, 1H), 7.59 (s, 1H), 7.37 (d, J = 8.0, 1H), 7.36 (s, 1H), 6.36 (d, J = 5.2, 1H), 6.23 (m, 1H), 3.66 (s, 2H), (m, 8H), 2.32 (q, J = 7.2 Hz, 2H), 2.14 (s, 3H), 0.98 (t, J = 7.2 Hz, 3H). MS (ESI) m/z 538 (M+H) +. 3-((1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)-4-methyl--(3-(4-methyl-1H-imidazol-1-yl)-5- (trifluoromethyl)phenyl)benzamide (12). 1 H MR (400 MHz, DMS) δ (bs, 1H), (s, 1H), 8.18 (s, 1H), 8.12 (s, 1H), 8.04 (s, 1H), 8.03 (d, J = 5.6 Hz, 1H), 7.85 (dd, J = 7.6, 1.6 Hz, 1H), 7.73 (d, J = 2.0 Hz, 1H), 7.65 (s, 1H), 7.54 (d, J = 8.0 Hz, 1H), 7.40 (s, 1H), 7.31 (m, 1H), 6.27 (d, J = 5.2, 1H), 6.15 (dd, J = 3.6, 2.0 Hz, 1H), 2.19 (s, 3H), 2.10 (s, 3H). MS (ESI) m/z 492 (M+H) +. S11
12 3-((7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-4-methyl--(3-(4-methylpiperazin-1-yl)-5- (trifluoromethyl)phenyl)benzamide (13). 1 H MR (400 MHz, DMS) δ (s,1h), 8.30 (s, 1H), 8.15 (s, 1H), 7.87 (d, J = 8.0 Hz, 1H), 7.84 (s, 1H), 7.66 (s, 1H), 7.60 (s, 1H), 7.53 (d, J = 8.0 Hz, 1H), 7.50 (d, J = 3.6, 1H), 6.93 (s, 1H), 6.55 (d, J = 3.2, 1H), 3.19 (t, J = 5.2 Hz, 4H), 2.45 (t, J = 5.2 Hz, 4H), 2.22 (s, 3H), 2.17 (s, 3H). MS (ESI) m/z 511 (M+H) +. -(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-(2-(4-methoxy-1Hpyrrolo[2,3-b]pyridin-5-yl)ethyl)-4-methylbenzamide (14). 1 H MR (600 MHz, DMS) δ (br, 1H), (s, 1H), 8.28 (s, 1H), 8.13 (m, 1H), 7.98 (d, J = 8.4 Hz, 1H), 7.90 (d, J = 8.4 Hz, 1H), 7.90 (m, 2H), 7.39 (m, 2H), 6.79 (s, 1H), 4.34 (s, 3H), 3.66 (s, 2H), 2.95 (m, 4H), (m, 10H), 2.43 (s, 3H), 1.08 (m, 3H). MS (ESI) m/z 580 (M+H) +. -(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-((4-methoxy-1H-pyrrolo[2,3- b]pyridin-5-yl)methoxy)-4-methylbenzamide (15). 1 H MR (600 MHz, DMS) δ (br, 1H), (s, 1H), 9.81 (br, 1H), 8.40 (s, 1H), 8.17 (m, 1H), 7.85 (m, 1H), 7.78 (m, 1H), 7.48 (m, 2H), 7.37 (m, 1H), 7.20 (s, 1H), 5.37 (s, 2H), 4.50 (s, 3H), 3.66 (s, 2H), (m, 10H), 2.55 (s, 3H), 1.34 (m, 3H). MS (ESI) m/z 582 (M+H) +. S12
13 4-methyl--(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-3-((6- (methylamino)pyrimidin-4-yl)oxy)benzamide (16). 1 H MR (400 MHz, DMS) δ (s, 1H), 8.26 (s, 1H), 8.22 (s, 1H), 8.12 (s, 1H), 7.83 (d, J = 8.0 Hz, 1H), 7.75 (s, 1H), 7.74 (s, 1H), 7.52 (d, J = 8.4 Hz, 1H), 7.50 (d, J = 8.0 Hz, 1H), 7.36 (m, 1H), 2.79 (s, 3H), 2.50 (s, 3H), 2.19 (s, 3H). 13 C MR (100 MHz, DMS) δ , , , , , , , , , , , , , , , , , , , 16.48, MS (ESI) m/z 483 (M+H) +. 4-methyl-3-((6-(methylamino)pyrimidin-4-yl)oxy)--(3-(4-methylpiperazin-1-yl)-5- (trifluoromethyl)phenyl)benzamide (17). 1 H MR (600 MHz, DMS) δ (s, 1H), 8.10 (br, 1H), 7.80 (d, J = 8.4 Hz, 1H), 7.69 (s, 1H), 7.64 (s, 1H), 7.60 (s, 1H), 7.47 (d, J = 7.8 Hz, 1H), 7.32 (d, J = 3.6 Hz, 1H), 6.92 (s, 1H), 5.74 (br, 1H), 3.18 (t, J = 4.8 Hz, 4H), 2.76 (br, 3H), 2.44 (t, J = 4.8 Hz, 4H), 2.21 (s, 3H), 2.15 (s, 3H). 13 C MR (100 MHz, DMS) δ , , , , , , , , , , , , , 54.79, 48.02, 46.12, MS (ESI) m/z 500 (M+H) +. S13
14 (E)--(4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-(2-(4- methoxy-1h-pyrrolo[2,3-b]pyridin-5-yl)vinyl)-4-methylbenzamide (18). 1 H MR (600 MHz, DMS) δ (s, 1H), (s, 1H), 8.53 (s, 1H), 8.24 (s, 1H), 8.20 (s, 1H), 8.12 (d, J = 8.4 Hz, 1H), 7.77(d, J = 8.4 Hz, 1H), 7.71 (d, J = 7.8 Hz, 1H), (m, 4H), 6.88 (s, 1H), 4.37 (s, 3H), 3.74 (s, 2H), (m, 7H), 2.76 (s, 6H), 2.46 (s, 3H). MS (ESI) m/z 582 (M+H) +. H F F F H 19 (E)-3-(2-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-5-yl)vinyl)-4-methyl--(4-((1- methylpiperidin- 4-yl)oxy)-3-(trifluoromethyl)phenyl)benzamide (19). 1 H MR (600 MHz, DMS) δ (br, 1H), (s, 1H), 9.41 (br, 1H), 8.50 (s, 1H), 8.18 (s, 1H), 8.13 (m, 1H), 8.02 (s, 1H), 7.75 (d, J = 7.8 Hz, 1H), 7.41 (d, J = 5.4 Hz, 1H), 7.40 (m, 3H), 6.84 (s, 1H), 4.35 (s, 3H), 3.42 (m, 1H), 3.07 (m, 2H), 2.81 (s, 3H), 2.46 (s, 3H), 2.25 (m, 2H), 2.13 (m, 2H), 2.00 (m, 2H). MS (ESI) m/z 565 (M+H) +. (E)--(3-(2-cyanopropan-2-yl)phenyl)-3-(2-(4-methoxy-1H-pyrrolo[2,3-b] pyridin-5-yl)vinyl)-4- methylbenzamide (20). 1 H MR (600 MHz, DMS) δ (br, 1H), (br, 1H), 8.36 (s, 1H), 7.98 (s, 1H), 7.76 (s, 1H), 7.58 (m, 2H), (m, 4H), 7.02 (s, 1H), 6.74 (s, 1H), 4.20 (s, 3H), 2.23 (s, 3H), 1.48 (s, 6H). MS (ESI) m/z 451 (M+H) +. S14
15 3-(2-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-5-yl)ethyl)-4-methyl--(3-(4-methyl-1H-imidazol-1- yl)-5-(trifluoromethyl)phenyl)benzamide (21). 1 H MR (600 MHz, DMS) δ (br, 1H), (s, 1H), 8.63 (s, 1H), 8.51 (m, 1H), 8.45 (m, 1H), 8.36 (s, 1H), 8.26 (s, 1H), (m, 3H), 7.26 (m, 1H), 4.74 (s, 3H), 3.42 (m, 1H), 3.05 (m, 2H), 3.02 (s, 3H), 3.01 (s, 3H), 2.99 (s, 4H), 2.77 (m, 2H), 2.44 (m, 2H), 2.23 (m, 2H). MS (ESI) m/z 567 (M+H) +. 4-((4-ethylpiperazin-1-yl)methyl)--(3-(2-(4-methoxy-1H-pyrrolo[2,3-b] pyridin-5- yl)ethyl)phenyl)-3-(trifluoromethyl)benzamide (22). 1 H MR (600 MHz, DMS) δ (br, 1H), (s, 1H), 9.44 (br, 1H), 8.36 (s, 1H), 8.03 (m, 1H), 7.72 (s, 1H), 7.48 (m, 1H), (m, 4H), 6.66 (s, 1H), 4.42 (s, 3H), 3.86 (s, 2H), 3.04 (m, 4H), (m, 10H), 1.31 (m, 3H). MS (ESI) m/z 566 (M+H) +. S15
16 -(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-(2-(4-methoxy-1Hpyrrolo[2,3-b]pyridin-5-yl)ethyl)benzamide (23). 1 H MR (600 MHz, DMS) δ (br, 1H), (s, 1H), 8.28 (s, 1H), 8.15 (d, J = 9.0 Hz, 1H), 8.04 (s, 1H), 7.92 (s, 1H), 7.86 (d, J = 7.2 Hz, 1H), 7.77 (d, J = 8.4 Hz, 1H), 7.51 (m, 3H), 6.91 (s, 1H), 4.38 (s, 3H), 3.72 (s, 2H), 3.00 (s, 4H), (m, 8H), 2.44 (m, 2H), 1.29 (m, 3H). MS (ESI) m/z 566 (M+H) +. (E)--(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-(2-(4-methoxy-1Hpyrrolo[2,3-b]pyridin-5-yl)vinyl)benzamide (24). 1 H MR (600 MHz, DMS) δ (br, 1H), (s, 1H), 8.57 (s, 1H), 8.11 (s, 1H), 7.72 (m, 5H), 7.35 (m, 4H), 6.80 (m, 1H), 4.34 (s, 3H), 3.68 (s, 2H), (m, 10H), 1.19 (s, 3H). MS (ESI) m/z 564 (M+H) +. -(4-(4-ethylpiperazin-1-yl)-3-(trifluoromethyl)phenyl)-3-(2-(4-methoxy-1H-pyrrolo[2,3- b]pyridin-5-yl)ethyl)-4-methylbenzamide (25). 1 H MR (600 MHz, DMS) δ (s, 1H), (s, 1H), 8.17 (s, 1H), 8.13 (s, 1H), 8.09 (d, J = 9.0 Hz, 1H), 7.79 (s, 1H), 7.75 (d, J = 8.4 Hz, 1H), 7.56 (d, J = 8.4 Hz, 1H), 7.51 (s, 1H), 7.31 (d, J = 7.8 Hz, 1H), 7.00 (s, 1H), 4.40 (s, 3H), 3.56 (m, 2H), 3.23 (m, 2H), 3.08 (m, 6H), 2.90 (s, 4H), 2.36 (s, 3H), 1.24 (t, J = 6.6 Hz, 3H). MS (ESI) m/z 566 (M+H) +. S16
17 (E)--(4-((4-ethylpiperazin-1-yl)methyl)phenyl)-3-(2-(4-methoxy-1H-pyrrolo[2,3-b]pyridin- 5- yl)vinyl)-4-methylbenzamide (26). 1 H MR (600 MHz, DMS) δ (br, 1H), (s, 1H), 8.50 (s, 1H), 8.17 (s, 1H), 7.78 (m, 1H), 7.74 (d, J = 8.4 Hz, 1H), (m, 6H), 6.85 (s, 1H), 4.35 (s, 3H), 3.39 (s, 2H), (m, 10H), 2.52 (s, 3H), 1.17 (m, 3H). MS (ESI) m/z 510 (M+H) +. S17
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SUPPORTING INFORMATION Pyrrolo[2,3-d:5,4-d']bisthiazoles: Alternate Synthetic Routes and a Comparative Study to Analogous Fused-ring Bithiophenes Eric J. Uzelac, Casey B. McCausland, and Seth C. Rasmussen*
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Supporting Information. Palladium Complexes with Bulky Diphosphine. Synthesis of (Bio-) Adipic Acid from Pentenoic. Acid Mixtures.
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chlorostibine Iou-Sheng Ke and François P. Gabbai Department of Chemistry, Texas A&M University, College Station, TX
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