A.A.E. Mourad and M.A.E. Mourad
LifeSciences259(2020)118270
12.87 (s, 1H, NH), 7.92–7.18 (m, H5-thiazole, 13AreH), 5.08 (s, 2H,
CH2); 13C NMR (100 MHz, DMSO‑d6): δ 168.52 (CONCO), 168.08
(CONH), 158.35 (C2-thiazole), 150.01 (C4-thiazole), 137.65
(AreC),136.60 (AreC), 135.35 (2AreC),135.01 (2AreC), 133.32
(2AreC), 132.12 (AreC), 131.70 (AreC), 129.90 (AreC), 128.84
(2AreC), 128.11 (AreC), 127.62 (AreC), 126.88 (AreC), 123.77
(2AreC), 108.89 (C5-thiazole). MS: m/z 439 (M+). Anal. Calcd. for
CH2). MS: m/z 518 (M+). Anal. Calcd. for C25H16 BrN3O3S (518.38): C,
57.92; H, 3.11; N, 8.11; S, 6.19. Found C, 57.61; H, 3.12; N, 8.25; S,
5.85.
8.2.2.8. 2-((1,3-Dioxoisoindolin-2-yl)methyl)-N-(4-(2-hydroxyphenyl)
thiazol-2-yl)benzamide (7g). Pale yellow solid, 0.143 g (97%), m.p.
182–184 °C. FTIR (KBr, cm−1): 3439 (NH), 3065 (Ar-CH), 2926 (Aliph.-
CH), 1772, 1712 (CO), 1609, 1578 (C=N). 1H NMR (400 MHz,
DMSO‑d6): δ 12.52 (s, 1H, NH), 7.91–6.76 (m, H5-thiazole, 12AreH),
5.71 (s, 1H, OH), 5.19 (s, 2H, CH2); 13C NMR (100 MHz, DMSO‑d6): δ
168.67 (CONCO), 168.38 (CONH), 157.37 (C2-thiazole), 155.84 (C4-
thiazole), 149.58 (AreC), 147.21 (AreC), 135.86 (AreC), 135.21
(AreC), 135.00 (AreC), 132.84 (AreC), 132.17 (2AreC), 131.71
(AreC), 129.71 (2AreC), 129.17 (AreC), 127.66 (AreC), 126.72
(AreC), 125.26 (AreC), 123.72 (2AreC), 121.42 (AreC),108.89 (C5-
thiazole). MS: m/z 455 (M+). Anal. Calcd. for C25H17N3O3S (455.49):
C, 65.92; H, 3.76; N, 9.23; S, 7.04. Found C, 65.61; H, 3.98; N, 9.50; S,
7.05.
C
25H17N3O3S (439.49): C, 68.32; H, 3.90; N, 9.56; S, 7.30. Found C,
68.01; H, 4.12; N, 9.77; S, 7.75.
8.2.2.3. 2-((1,3-Dioxoisoindolin-2-yl)methyl)-N-(4-(p-tolyl)thiazol-2-yl)
benzamide (7b). White solid, 0.122 g (82%), m.p. 250–252 °C. FTIR
(KBr, cm−1
) ν: 3453, 3298 (NH), 3098 (Ar-CH), 2923 (Aliph.-
CH),1768, 1707, 1662 (CO), 1575 (C=N). 1H NMR (400 MHz,
DMSO‑d6): δ 12.60 (s, 1H, NH), 7.85–7.25 (m, H5-thiazole, 12AreH),
5.07 (s, 2H, CH2), 2.36 (s, 3H, CH3); 13C NMR (100 MHz, DMSO‑d6): δ
168.16 (CONCO), 167.30 (CONH), 158.45 (C2-thiazole), 149.67 (C4-
thiazole), 137.57 (AreC), 135.70 (2AreC), 134.67 (AreC), 132.45
(AreC), 132.19 (AreC), 130.70 (AreC), 129.89 (2AreC), 129.73
(AreC), 128.17 (AreC), 127.79 (AreC), 127.08 (2AreC), 126.21
(2AreC), 123.66 (2AreC), 108.03 (C5-thiazole), 21.24 (CH3). MS: m/
z 453 (M+). Anal. Calcd. for C26H19N3O3S (453.51): C, 68.86; H, 4.22;
N, 9.27; S, 7.07. Found C, 68.55; H, 4.10; N, 9.52; S, 7.33.
8.2.2.9. 2-((1,3-Dioxoisoindolin-2-yl)methyl)-N-(4-(3,4,5-
trimethoxyphenyl)thiazol-2-yl)benzamide (7h). White solid, 0.117g
(78%), m.p. 218–220 °C. FTIR (KBr, cm−1) ν: 3468 (NH), 3069 (Ar-
CH), 2936 (Aliph.-CH), 1775, 1716 (CO), 1604, 1539 (C=N). 1H NMR
(400 MHz, DMSO‑d6): δ 12.86 (s, 1H, NH), 7.89–6.86 (m, H5-thiazole,
10AreH), 5.19 (s, 2H, CH2), 3.87 (s, 6H, 2 OCH3), 3.71 (s, 3H, 1 OCH3).
MS: m/z 529 (M+). Anal. Calcd. for C28H23N3O6S (529.56): C, 63.51; H,
4.38; N, 7.93; S, 6.05. Found C, 63.82; H, 4.45; N, 7.70; S, 6.16.
8.2.2.4. 2-((1,3-Dioxoisoindolin-2-yl)methyl)-N-(4-(4-methoxyphenyl)
thiazol-2-yl)benzamide (7c). White solid, 0.119
g
(80%), m.p.
185–187 °C. FTIR (KBr, cm−1) ν: 3439, 3238 (NH), 3063 (Ar-CH),
2971 (Aliph.-CH), 1768,1708, 1670 (CO), 1609, 1579 (C=N). 1H NMR
(400 MHz, DMSO‑d6): δ 12.69 (s, 1H, NH), 7.92–6.78 (m, H5-thiazole,
12AreH), 5.07 (s, 2H, CH2), 3.79 (s, 3H, OCH3). MS: m/z 469 (M+).
Anal. Calcd. for C26H19N3O4S (469.51): C, 66.51; H, 4.08; N, 8.95; S,
6.83. Found C, 66.21; H, 4.12; N, 9.11; S, 6.52.
Funding
This research did not receive any specific grant from funding
agencies in the public, commercial, or not-for-profit sectors.
8.2.2.5. N-(4-(4-Clorophenyl)thiazol-2-yl)-2-(1,3-dioxoisoindolin-2-yl)
benzamide (7d). White solid, 0.125 g (84%), m.p. 210–212 °C, FTIR
(KBr, cm−1) ν: 3460, 3232 (NH), 3061 (Ar-CH), 2973 (Aliph.-CH),
1768, 1670 (CO), 1577, 1542 (C=N). 1H NMR (400 MHz, DMSO‑d6): δ
12.66 (s, 1H, NH), 7.95–7.34 (m, H5-thiazole, 12AreH), 5.07 (s, 2H,
CH2); 13C NMR (100 MHz, DMSO‑d6): δ 168.19 (CONCO), 167.44
(CONH), 158.73 (C2-thiazole), 148.33 (C4-thiazole), 135.24 (2AreC),
135.09 (2AreC), 133.93 (AreC),133.76 (AreC), 132.84 (AreC),
131.62 (AreC),130.45 (AreC), 129.00 (AreC), 128.70 (AreC),
127.76 (2AreC), 127.55 (AreC), 125.91 (2AreC), 123.96 (2AreC),
109.61 (C5-thiazole). MS: m/z 473 (M+). Anal. Calcd. for C25H16N3O3S
(473.93): C, 63.36; H, 3.40; N, 8.87; S, 6.77. Found C, 63.20; H, 3.52; N,
9.07; S, 6.75.
Declaration of competing interest
The authors declare that there are no conflicts of interest.
Appendix A. Supplementary data
Supplementary data to this article can be found online at https://
References
[1] M. Rewers, J. Ludvigsson, Environmental risk factors for type 1 diabetes, Lancet
S.R. Bornstein, An update on preventive and regenerative therapies in diabetes
8.2.2.6. 2-((1,3-Dioxoisoindolin-2-yl)methyl)-N-(4-(4-nitrophenyl)
thiazol-2-yl)benzamide (7e). Yellow solid, 0.118
g (79%), m.p.
245–247 °C. FTIR (KBr, cm−1): 3399, 3306 (NH), 3146 (Ar-CH),
2766 (Aliph.-CH), 1774, 1717, 1641 (CO), 1594, 1537 (C=N). 1H
NMR (400 MHz, DMSO‑d6): δ; 12.34 (s, 1H, NH), 8.29–7.12 (m, H5-
thiazole, 12ArH), 5.07 (s, 2H, CH2). 13C NMR (100 MHz, DMSO‑d6): δ
168.13 (CONCO), 167.77 (CONH), 158.85 (C2-thiazole), 150.04 (C4-
thiazole), 147.80 (AreC), 136.03 (AreC), 135.77 (AreC), 135.11
(2AreC), 134.17 (AreC), 133.35 (AreC), 132.00 (2AreC), 131.70
(AreC), 129.12 (2AreC), 127.42 (2AreC), 127.15 (AreC), 125.42
(AreC), 123.66 (2AreC), 106.89 (C5-thiazole). MS: m/z 484 (M+).
Anal. Calcd. for C25H16N4O5S (484.48): C, 61.98; H, 3.33; N, 11.56; S,
6.62. Found C, 62.21; H, 3.52; N, 11.32; S, 6.75.
PPAR-signaling and metabolism: the good, the bad and the future, Nat. Med. 19
entiation, and cell growth, J. Biol. Chem. 276 (2001) 37731–37734, https://doi.
Winter, D. Porte, C.F. Semenkovich, S. Smith, L.H. Young, R. Kahn,
Thiazolidinedione use, fluid retention, and congestive heart failure: a consensus
statement from the American Heart Association and American Diabetes Association,
A. Elbrecht, B.A. Johnson, G. Zhou, T.W. Doebber, Distinct properties and ad-
vantages of a novel peroxisome proliferator-activated protein [gamma] selective
8.2.2.7. N-(4-(4-Bromophenyl)thiazol-2-yl)-2-(1,3-dioxoisoindolin-2-yl)
benzamide (7f). White solid, 0.123 g (82%), m.p. 200–202 °C. FTIR
(KBr, cm−1) ν: 3457, 3236 (NH), 3063 (Ar-CH), 2926 (Aliph.-CH),
1771,1670 (CO), 1607, 1576 (C=N). 1H NMR (400 MHz, DMSO‑d6): δ
12.97 (s, 1H, NH), 7.92–7.19 (m, H5-thiazole, 12AreH), 5.19 (s, 2H,
14