2-Amino Benzamide

Labeling Glycans with Fluorescent2-Aminopyridine, 2-Amino Benzamide, or Anthraniiic Acid... 

Bigge, J.C., Patel, T.P., Bruce, J.A., Goulding, P.N., Charles, S.M., and Parekh, R.B. (1995) Nonselective and efficient fluorescent labeling of glycans using 2-amino benzamide and anthranilic acid. Anal. Biochem. 230, 229-238. 

Amino-4-hydroxy- E9b/2, 29 (2-Amino-benzamid + H2N — CN) 4-Amino-2-hydroxy- E9b/2, 33 (2-CN —anilin + C1-S02-NCO)... 

Bei der Bildung der 2-Amino-benzamide aus 2-Nitro-benzonitrilen wird das Sauer-stoff-Atom vom intermediar-gebildeten N-Phenyl-hydroxylamin infolge voriibergehen-der Cyclisierung zum 3-Amino-l,2-benzoxazol auf die Cyan-Gruppe iibertragen1 2. 

Cyclization of 2-aminobenzamide derivatives constitute the main synthetic approach to the 2,1,3-benzothiadiazine nucleus. 2,l,3-Benzothiadiazin-4(3//)-one 2,2-dioxides are available by the action of sulfamoyl chloride on methyl anthranilate, by treatment of 2-methylpyridinium salts of 2-sulfamoylbenzamides with phosphorus oxychloride (Section 6.16.9.1.2), by base-catalysed cyclization of A -(2-aminocarbonyl)sulfamides (Section 6.16.9.1.2), and by cyclization of 2-amino-benzamides with thionyl chloride (Section 6.16.2.3.1). 

Beilstein Handbook Reference) A13-28018 Aminobenzamide o-Aminobenzamide Anthra-nilamide Anlhranilimidic acid Benzamide, 2-amino- Benzamide, o-amino-Benzoic acid, 2-amino-, amide BRN 0508509 EINECS 201-851-2 HSDB 5261 NSC 38768. Has antiviral xtivity see USP 5,763,464. Also has anti-coagulant properties (USP 6,498,185). Solid mp = 110.5 bp = 300 Xm = 213, 243 nm (MeOH) very soluble in EtOAc, soluble in H2O, EtOH, less soluble in Et20. CeHe. BASF Cap. La-Co Industries Ledger... 

More recently, Patil et al. reported a cascade reaction of 2-aminobenzaldehydes and 2-amino benzamides by combining chiral Brpnsted acid and achiral gold catalysis [76]. The attractive optically pure 1,2-dihydroisoquinolines were prepared by chiral phosphoric acid-catalyzed asymmetric condensation of alkyne-tethered aldehydes with 2-aminobenzamides to give rise to the chiral aminal 136, which was followed... 

In cases where decarboxylation is anticipated, the quinazolinone could be obtained by heating ammonium o-formamidobenzoate or o-forra ami do benz amide for several hours. This ring closure could be effected more conveniently by boiling the o-formamidobenzamide with 3% aqueous sodium hydroxide for a few minutes, o-Amino-benzamides have also been converted to quinazolinones by refluxing with ethyl orthoformate alone or preferably in the presence of acetic anhydride. ... 

Substituted (l//,3 -quinazol>ne-2,4-diones 774, as well as the 3-unsubstituted parent compound 774 (R = H), are available by treatment of 2-[(trichloroacetyl)amino]benzamides 772 with sodium hydroxide in DMSO. The reaction proceeds via intermediate isocyanate compounds 773 which undergo ring closure to the final products <20050PP560>. 

Rhodium-catalyzed hydroformylation of -(substituted amino)benzyl-amines (387, X = H2) and -(substituted amino)benzamides (387, R = H, X = O) in the presence of rhodium(II) acetate dimer and triphenylphos-phine in deoxygenated ethyl acetate gave a 7 3 mixture of 1,2,3,4,4 ,5-hexahydro-6//-pyrido[l,2-a]quinazolines (388, X = H2,0) and isomeric 3-methyl-l,2,3,3fl,4,5-hexahydropyrrolo[l,2-a]quinazolines (389, X = H2, O) (94AJC1061). The methyl derivative of benzylamine 387 (R = Me, X = H2) afforded a mixture of diastereoisomers 390 and 391 (X = H2). Their ratio depended on the reaction time. Longer reaction times gave more 391 (X = H2), containing the methyl group in an equatorial position. Compound 390 isomerized into 391 (X = H2), under the aforementioned conditions. The benzamide derivative (387, R = Me, X = O) yielded only one isomer (391, X = O), independent of the reaction period. 

The N-(2-diethylamino-ethyl)-4-nitro-benzamide was reduced by hydrogen Ni as catalyst to give N-(2-diethylamino-ethyl)-4-amino-benzamide (procainamide). 

The method is of great value in dealing with substances which are sensitive to strong acids or bases, such as o-nitro- and amino-benzaldehydes, nitro- and amino-benzamides and benzoylureas, and is also of service in the preparation of other ammo acids. 

When treated in water with ammonia, 2-aminobenzamide is quickly and quantitatively formed, and organic amines react similarly. These amino-benzamides can be used in all the syntheses described in Section VII,A. Conditions can be arranged so that a further reaction proceeds spontaneously, as when 5,7-dichloroisatoic anhydride gives a moderate yield of 6,8-dichloroquinazoline-2,4-dione when gently refluxed in aqueous ammonia for 1 hr.251,377 Isatoic anhydride can easily be N-alkylated or N-arylated with the appropriate halide or tosylate and potassium carbonate or sodium hydride.378... 

Fig. 6a,b. ADPRT inhibitors block chick myoblast differentiation but not proliferation, a 3-amino-benzamide 3-aminobenzoate 3-methoxybenzamide 3-methoxybenzoate O nicotinamide, b 8 xM 3-aminobenzamide 10 mM 3-aminobenzamide 20 mM 3-aminobenzamide 5 mM 3-methoxybenzamide 18 mM 3-methoxybenzamide no inhibitor... 

Inhibition of poly(ADP-ribosylation) by benzamide (BA) or 3-amino-benzamide (3AB) for a brief period (i.e., during which ADP-ribosylation following DNA damage is elevated in untreated cells) during MNNG-induced DNA damage to BALB/3T3 cells significantly (3-30-fold) enhanced transformation frequency (Table 1). 

Fig. 4. Poly(ADP-ribose) synthetase activity in isolated nuclear matrices. Isolated nuclei matrices were incubated with 10 tiM [ P]-NAD in buffer A at 25°C for the times indicated. Assay of enzyme activity as in Methods. Without further addition in the presence of 10 mM 3-amino-benzamide...

Mouse leukaemia LI 210 cells were treated with methylnitrosourea (to aout 10% survival) and after suspension in fresh medium and growth for 2 days to allow expression of the mutations, a recycling enrichment method of selection was carried out. This involved expQsing the cells to DMS and SAB simultaneously. The DMS concentration was chosen such that there was more than 90% survival in the absence of S-amino-benzamide, but less than 10% survival in its presence. After eight cycles of this treatment (SO juAf DMS, 2 roM SAB), cells were treated with 60 ijM DMS and 2 raM S-amino-benzamide (1.0% survival of mutagenised cells, 0.4% survival of parental cells). The cells were then cloned. 

Normally, most trypomastigotes are released 4 or 5 days after the original infection (Fig. 1). However, in. the presence of the ADP-ribosyltransferase inhibitor, 3-amino-benzamide [9], release was significantly and reproducibly delayed (Fig. 1 A). The presence of 3-aminobenzoic acid produced no significant effect. Stronger inhibitory effects were produced by other enzyme inhibitors. 5-Methylnicotinamide [10] (Fig. IB) and 3-methoxybenzamide [9] (Fig. 1C) almost totally blocked the appearance of the... 

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