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Volumn 5, Issue 1, 2008, Pages 3-7

Synthesis and antibacterial activity of new (2,3-dioxo-indolin-1-yl) acetamides

(10) Bouhfid, R a Joly, N b Ohmani, F c Essassi, E M a Lequart, V b Banoub, J d Kheddid, K c Charof, R c Massoui, M a Martin, Patrick b

a FACULTÉ DES SCIENCES (Morocco)

b Centre Hospitalier de Bethune (France)

c INSTITUT NATIONAL D HYGIÈNE (Morocco)

d FISHERIES AND OCEANS CANADA (Canada)

Author keywords

Acetamide; In vitro biological activity; Isatin; Tertiary amide

Indexed keywords

EID: 38949084887 PISSN: 15701786 EISSN: None Source Type: Journal
DOI: 10.2174/157017808783330199 Document Type: Article

Times cited : (14)

References (25)

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13
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- Bouhfid, R.; Joly, N.; Massoui, M.; Cecchelli, R.; Lequart, V.; Martin, P.; Essassi, E.M. Heterocycles, 2005, 56, 2949.
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14
- 38949188400
- 2-Ethozycarbonylmethylisatin (3a) was obtained as yellow crystals (mp 112°C, 1H NMR (300 MHz, CDCl3, δ1.32 (t, J, 7.1 Hz, 3H, CH3, 4.33 (q, J, 7.1 Hz, 2H, O-CH2, 4.60(s, 2H, N-CH2, 6.85-7.66 (m, 4H, HAr, 13C NMR (300 MHz, CDCl3, δ 14.1 (CH3, 41.4 (N-CH2, 63.6 (O-CH2, 110.8, 125.5, 126.6, 139.5 (4 CHAr, 117.9 (CAr-C=N, 150.3 (CAr-N-C=O, 168.2 (C=O amide, 172.2 (C=O ester, 182.5 C-O ketone, EMS [M, m/z 233. Anal. Calcd for C12H11NO4: C, 61.79; H, 4.76; N, 6.01, Found: C, 61.68; H, 4.81; N, 5.93
- 4: C, 61.79; H, 4.76; N, 6.01%. Found: C, 61.68; H, 4.81; N, 5.93%.

15
- 38949118426
- 2-Ethoxycarbonylmethyl-5-chloriosatin (3b) was obtained as yellow crystals (mp 128*C, 1H NMR (300 MHz, CDCl3, δ1.30 (t, 3H, CH3, 3J=7.1 Hz, 4.27 (q, 2H, OCH2, 3J+7.1 Hz, 4.51 (s, 2H, NCH2, 6.75-7.63 (m, 3H, HAr, 13C NMR (300 MHz, CDCl3, δ 14.5 (CH3, 41.8 (NCH2, 62.7 (OCH2) 111.9, 125.8, 138.2(CHAr, 118.4, 130.4, 150.1 (Cq, 157.9(C=O)amide; 166.9(C=O)ester, 181.9(C=O)ketone. EIMS [M, m/z 267. Anal. Calcd for C12H10CINO4: C, 53.85; H, 3.77; N, 5.23, Found: C, 53.65; H, 3.87; N, 5.32
- 4: C, 53.85; H, 3.77; N, 5.23%. Found: C, 53.65; H, 3.87; N, 5.32%.

16
- 38949208573
- 2-(2,3-Dioxoindolin-1-yl)aceric acid 4a was obtained as yellow crystals (mp 196°C, 1H NMR (300 MHz, CDCl3, δ4.48 (s, 2H, NCH2, 6.75-7.53 (m, 4H, HAr, 13.31 (s,1H, OHacid, 13C NMR (300 MHz, CDCl3, δ41.8 (NCH2, 113.4, 124.5, 126.1, 137.8 (CHAr, 119.0, 149.6 (Cq, 158.3 (C=Oamide, 169.1 (C=Oacid, 182.2 C=Oketone, EIMS [M, m/z 205. Anal. Calcd for C10H7NO4: C, 58.54; H, 3.44; N, 6.83, Found: C, 58.67; H, 3.55; N, 6.66
- 4: C, 58.54; H, 3.44; N, 6.83%. Found: C, 58.67; H, 3.55; N, 6.66%.

17
- 38949154264
- 2-(5-Chloro-2,3-dioxoindolin-1-yl)acetic acid 4b was obtained as yellow crystals (mp 178°C, 1H NMR (300 MHz, CDCl3, δ4.52 (s, 2H, NCH2, 7.23-7.76 (m, 3H, HAr, 13.35 (s,1H, OHacid, 13C NMR (300 MHz, CDCl3, δ43.1 (NCH2, 112.6, 125.3, 138.2 (CHAr, 120.1, 127.7, 148.5, 159.4 (Cq, 170.0 (C=Oacid, 183.3 C=Oketone, EIMS [M, m/z 239. Anal. Calcd for C10H6ClNO4: C, 50.13; H, 2.52; N, 5.85, Found: C, 49.97; H, 2.59; N, 5.93
- 4: C, 50.13; H, 2.52; N, 5.85%. Found: C, 49.97; H, 2.59; N, 5.93%.

18
- 0033525680
- Slocum, D.W.; Dietzel, P. Tetrahedron Lett., 1999, 40, 1823.
- (1999) Tetrahedron Lett , vol.40 , pp. 1823
- Slocum, D.W.¹ Dietzel, P.²

19
- 38949217210
- 2-(2,3-dioxoindolin-1-yl)-N,N-diethylacetamide (8a) was obtained as yellow crystals with 74% yield, mp 154°C, 1H NMR (300 MHz, CDCl3, δ1.02-1.22 (m, 6H, 2CH3, 3.30-3.41 (m, 4H, 2CH2, 4.64 (s, 2H, NCH2, 7.03-7.69 (m, 4HAr, 13C NMR (300 MHz, CDCl3, δ13.3, 14.5 (CH3, 41.7, 40.3, 41.1 (NCH2, 111.7, 123.7, 124.8, 138.9(CHAr, 117.7, 151.9, 158.8 (Cq, 164.7 (C=Oacetamide, 183.7 C=Oketone, EIMS [M, m/z 260. Anal. Calcd for C14H16N2O3: C, 64.60; H, 6.20; N, 10.76, Found: C, 64.73; H, 6.12; N, 10.82
- 3: C, 64.60; H, 6.20; N, 10.76%. Found: C, 64.73; H, 6.12; N, 10.82%.

20
- 38949175906
- 2-(5-chloro-2,3-dioxoindolin-1-yl)-N,N-diethylacetamide (8b) as yellow crystals in 70% yield, mp 144°C, 1H NMR (300 MHz, CDCl3, δ1.07-1.25 (m, 6H, 2CH3, 3.27-3.42 (m, 4H, 2NCH2, 4.66 (s, 2H, NCH2, 7.09-7.74 (3H, HAr, 13C NMR (300 MHz, CDCl3, δ13.3, 14.5 (CH3, 41.1, 41.8 (NCH2, 113.6, 124.3, 137.8 (CHAr, 118.9, 128.0, 150.4, 158.5 (Cq, 164.6 (C=Oacetamide, 182.6 C=Oketone, EIMS [M, m/z 294. Anal. Calcd for C14H15ClN2O3: C, 57.05; H, 5.13; N, 9.50, Found: C, 56.92; H, 5.05; N, 9.65
- 3: C, 57.05; H, 5.13; N, 9.50%. Found: C, 56.92; H, 5.05; N, 9.65%.

21
- 38949104936
- 2-(2,3-dioxoindolin-1-yl)-N-(p-chlorophenyl)-N-methylacetamide (9a) as yellow crystals in 65% yield, mp 186°C, 1H NMR (300 MHz, CDCl3, δ3.25 (s, 3H, CH3, 4.53 (s, 2H, NCH2, 6.82-7.73 (m, 8H, HAr, 13C NMR (300 MHz, CDCl3, δ28.8 (NCH3, 48.2 (NCH2, 115.3, 126.2, 128.7, 129.1, 129.7, 135.2, 143.2 (CHAr, 122.2, 141.6, 155.1, 162.8, 169.5 (Cq, 171.6 (C=Oacetamide, 187.3 C=Oketone, EIMS [M, m/z 328. Anal. Calcd for C17H13CIN2O3: C, 62.11; H, 3.99; N, 8.52, Found: C, 61.99; H, 4.06; N, 8.61
- 3: C, 62.11; H, 3.99; N, 8.52%. Found: C, 61.99; H, 4.06; N, 8.61%.

22
- 38949164880
- 2-(5-chloro-2,3-dioxoindolin-1-yl)-N-(p-chlorophenyl)-N- methylacetmdde (9b) as yellow crystals with 77% yield, mp 170°C, 1H NMR (300 MIiz, CDCl3, δ3.27 (s, 3H, NCH3, 4.17 (s, 2H, NCH2, 6.47-7.58 (m, 7K HAr, 13C NMR (300 MHZ, CDCl3, δ37.8 (NCH3, 42.0 (NCH2, 110.4, 113.3, 123.9, 125.5, 128.6, 128.9, 130.6, 138.3 (CHAr, 117.6, 134.8, 140.5, 141.9, 150.8, 158.2 (Cq, 165.1 (C=Oacetamide, 182.6 C=Oketone, EIMS [M, m/z 350. Anal. Calcd for C17H12Cl2N2O3: C, 56.22; H, 3.33; N, 7.71, Found: C, 56.15; H, 3.40; N, 7.68
- 3: C, 56.22; H, 3.33; N, 7.71%. Found: C, 56.15; H, 3.40; N, 7.68%.

23
- 38949200751
- 2-(2,3-dioxoindolin-1-yl)-N-methyl-N-phenylacetamide (10a) as yellow crystals with 68% yield, mp 188°C, 1H NMR (300 MHz, CDCl3, δ3.40 (s, 3H, CH3, 4.38 (s, 2H, NCH2, 6.77-7.68 (m, 9H, HAr, 13C NMR (300 MHz, CDCl3, δ38.6 (NCH3, 42.2 (NCH2, 110.4, 125.3, 126.0, 129.9, 130.9, 139.1 (CHAr, 117.4, 135.6, 140.6, 149.7 (Cq, 167.5 (C=Oacetamide, 182.2 C=Oketone, EIMS [M, m/z 294. Anal. Caled for C17H14N2O3: C, 69.38; H, 4.79; N, 9.52, Found: C, 69.25; H, 4.81; N, 9.38
- 3: C, 69.38; H, 4.79; N, 9.52%. Found: C, 69.25; H, 4.81; N, 9.38%.

24
- 38949136822
- 2-(5-chloro-2,3-dioxoindolin-1-yl)-N-methyl-N-phenylacetamide (10b) as yellow crystals with 63% yield, mp 172°C, 1H NMR (300 MHz, CDCl3, δ3.34 (s, 3H, CH3, 4.46 (s, 2H, NCH2, 6.52-7.61 (m, 8H, HAr, 13C NMR (300 MHz, CDCl3, δ25.2 (NCH3, 43.1 (NCH2, 113.2, 125.9, 129.1, 130.2, 138.7, 142.5 (CHAr, 123.1, 140.5, 152.3, 159.7, 168.3 (Cq, 171.6 (C=Oacetamide, 183.1 C=Oketone, EIMS [M, m/z 328. Anal. Calcd for C17H13CIN2O3. C, 62.11; H, 3.99; N, 8.52, Found: C, 62.26; H, 4.05; N, 8.36
- 3. C, 62.11; H, 3.99; N, 8.52%. Found: C, 62.26; H, 4.05; N, 8.36%.

25
- 0019209247
- Joshi, K.C.; Pathak, V.N.; Jain, S.K. Pharmazie, 1980, 35, 677.
- (1980) Pharmazie , vol.35 , pp. 677
- Joshi, K.C.¹ Pathak, V.N.² Jain, S.K.³

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