4195-21-5Relevant academic research and scientific papers
Synthesis of new 3-arylaminophthalides and 3-indolyl-phthalides using ammonium chloride, evaluation of their anti-mycobacterial potential and docking study
Patil, Avinash,Duggal, Harleen,Bagul, Kamini T.,Kamble, Sonali,Lokhande, Pradeep,Gacche, Rajesh,Meshram, Rohan
, p. 723 - 739 (2020/10/22)
Objective: The study aims at the derivatization of “Phthalides” and synthesizes 3-arylaminophthalides & 3-indolyl-phthalides compounds, and evaluates their anti-tubercular and antioxidant activities. The study has also intended to employ the in silico methods for the identification of possible drug targets in Mycobacterium and evaluate the binding affinities of synthesized compounds. Methods: This report briefly explains the synthesis of phthalide derivatives using ammonium chloride. The synthesized compounds were characterized using spectral analysis. Resazurin Microtiter Assay (REMA) plate method was used to demonstrate the anti-mycobacterial activity of the synthesized compounds. An in-silico pharmacophore probing approach was used for target identification in Mycobacterium. The structural level interaction between the identified putative drug target and synthesized phthalides was studied using Lamarckian genetic algorithm-based software. Results and Discussion: In the present study, we report an effective, environmentally benign scheme for the synthesis of phthalide derivatives. Compounds 5c and 5d from the current series appear to possess good anti-mycobacterial activity. dCTP: deaminasedUTPase was identified as a putative drug target in Mycobacterium. The docking results clearly showed the interactive involvement of conserved residues of dCTP with the synthesized phthalide compounds. Conclusion: On the eve of evolving anti-TB drug resistance, the data on anti-tubercular and allied activities of the compounds in the present study demonstrates the enormous significance of these newly synthesized derivatives as possible candidate leads in the development of novel anti-tubercular agents. The docking results from the current report provide a structural rationale for the promising anti-tubercular activity demonstrated by 3-arylaminophthalides and 3-indolyl-phthalides compounds.
The investigation of nucleophilic reactions of 3 -bromo/chloro phthalide with amines
Desai,Chaphekar,Samant
, p. 810 - 813 (2007/10/03)
The reaction of 3-bromo/chloro phthalide 1a/b with secondary amines in polar solvents gives the corresponding amides of 2-formylbenzoic acid, while in nonpolar solvents gives 3-aminophthalides. The reaction of 1a/b with aromatic primary amines gives 3-arylaminophthalides, while with aliphatic primary amines 3-hydroxyphthalimidines are obtained.
Pseudoacids. II. 2-Acylbenzoic Acid Derivatives
Valente, Edward J.,Martin, Samuel B.,Sullivan, Larry D.
, p. 264 - 276 (2007/10/03)
Structures of derivatives of cyclic o-acylbenzoic acids, including the chloride, endo- and exocyclic amides, esters and anhydrides, are examined. 3-Chloro-1(3H)-isobenzofuranone (1), orthorhombic, Pbca, a = 11.616 (5), b = 8.120 (3), c = 15.640 (9) A; 3-methoxy-3-phenyl-1(3H)-isobenzofuranone (3), orthorhombic, P212121, a = 6.923 (2), b = 8.291 (4), c = 21.551 (8) A; 3-hydroxy-3-phenyl-N-propyl-1(3H)-isoindolone (4), orthorhombic, P212121, a = 8.662 (4), b = 9.551 (7), c = 17.649 (14) A; 3-(N-morpholino)-1(3H)-isobenzofuranone (5), triclinic, P1, a = 6.172 (4), b = 11.163 (7), c = 17.33 (2) A, α = 105.91 (6), β = 99.85 (6), γ = 97.57 (5)°; 3-(2′-benzoylbenzoyloxy)-3-phenyl-1(3H)-isobenzofuranone (7), triclinic, P1, a = 9.694 (3), b = 10.505 (4), c = 11.163 (4) A°, α = 80.58 (3), β = 80.41 (3), γ = 76.49 (3)°; bis[1(3H)-isobenzofuranone-3-yl]ether (8), monoclinic, I2/a, a = 15.31 (2), b = 6.111 (12), c = 28.30 (5) A, β = 101.61 (12)°. An open oxoacid tertiary amide is also described: N-morpholino 2′-benzoylbenzamide (6): monoclinic, P21/c, a = 6.844 (4), b = 15.696 (8), c = 14.154 (7) A, β = 99.43 (4)°. Pseudoacid derivatives form planar isobenzofuran and isoindole rings, and the former aldehyde/ketone carbon-heteroatom endocyclic and exocyclic bond distances show bond length variations which correlate with the relative basicities of the attached groups. Structures of both endocyclic and exocyclic nitrogen pseudoamides are reported as well as examples of the normal-pseudoanhydride and the dipseudoanhydride.
Effect of Nucleophilicity and Leaving Group Ability on the SN2 Reactions of Amines with (Acyloxy)alkyl α-Halides: A Product Distribution Study
Sloan, Kenneth B.,Koch, Suzanne A. M.
, p. 635 - 640 (2007/10/02)
The course of the reaction of amines with (acyloxy)alkyl α-halides has been found to depend on the nucleophilicity of the amines and the leaving group ability of the halides.More nucleophilic amines tended to give acylated products 2 from the reaction while less nucleophilic amines gave alkylated products 3.The use of a better leaving group also tended to favor the formation of a greater amount of alkylated product.These results have been compared to the observations of Westaway on the effect of leaving group ability and nucleophilicity on the bond lengths in the transit ion state of SN2 reactions.In addition, secondary amines have been shown to cause the rearrangement of 2-formylbenzamides to 3-amino-1(3H)-isobenzofuranones.
