22780-31-0Relevant academic research and scientific papers
A new synthesis of 2-substituted 4H-3,1-benzoxazin-4-ones by cyanuric chloride cyclodehydration of N-benzoyl- and N-acylanthranilic acids
Khajavi, Mohammad S.,Shariat, Seyed M.
, p. 1159 - 1165 (2005)
A new and a convenient method for the synthesis of aryl- and alkyl-2-substituted 4H-3,1-benzoxazin-4-ones by cyclodehydration of N-benzoyl- and N-acylanthranilic acid by cyanuric chloride is described.
O-amino aromatic amide derivative as well as preparation method and application thereof
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Paragraph 0045-0047; 0049; 0103-0106; 0108, (2021/08/14)
The invention discloses an o-amino aromatic amide derivative as well as a preparation method and application thereof. The o-amino aromatic amide derivative is a compound with a structural general formula I, II and III or a pharmaceutically acceptable salt
N-Cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites
Chandrabalan, Arundhasa,McPhillie, Martin J.,Morice, Alyn H.,Boa, Andrew N.,Sadofsky, Laura R.
supporting information, p. 141 - 156 (2019/03/17)
The transient receptor potential ankyrin 1 (TRPA1) channel is a non-selective cation channel, which detects noxious stimuli leading to pain, itch and cough. However, the mechanism(s) of channel modulation by many of the known, non-reactive modulators has not been fully elucidated. N-Cinnamoylanthranilic acid derivatives (CADs) contain structural elements from the TRPA1 modulators cinnamaldehyde and flufenamic acid, so it was hypothesized that specific modulators could be found amongst them and more could be learnt about modulation of TRPA1 with these compounds. A series of CADs was therefore screened for agonism and antagonism in HEK293 cells stably transfected with WT-human (h)TRPA1, or C621A, F909A or F944A mutant hTRPA1. Derivatives with electron-withdrawing and/or electron-donating substituents were found to possess different activities. CADs with inductive electron-withdrawing groups were agonists with desensitising effects, and CADs with electron-donating groups were either partial agonists or antagonists. Site-directed mutagenesis revealed that the CADs do not undergo conjugate addition reaction with TRPA1, and that F944 is a key residue involved in the non-covalent modulation of TRPA1 by CADs, as well as many other structurally distinct non-reactive TRPA1 ligands already reported.
Synthesis and biological evaluation of some anthranilic acid and 2-phenylquinazoline-4(3H)-one analogues
Banerjee, Mrityunjay,Behera, Chinmoy C.,Pradhan, Guru C.,Azam, M. Afzal,Sahu, Susant K.
scheme or table, p. 134 - 142 (2010/08/07)
In the present investigation a novel series of N-(phenyl) chalconyl anthranilic acids containing pyrazolines (4a-j), tetra- hydropyrimidines (4k-o), tetrahydrothiopyrimidines (4p-t) and 2-phenylquinazolin-4(3iJ)-ones containing pyrazolines (8a-f), isoxazolines (8g-l), tetrahydropyrimidines (8m-r) and tetrahydrothiopyrimidines (8s-x) were synthesized and characterized by elemental analysis, FT-IR, 1H NMR and mass spectroscopy. The title compounds (4a-t) and (8a-x) were investigated for their analgesic, anti-inflammatory, antimicrobial and in vitro protein denaturation activities. Compounds 4j and 8x were identified as lead compounds with optimum analgesic, anti-inflammatory and antimicrobial activities.
Isoxazolinyl derivatives of anthranilic acid as antiinflammatory agents
Rani, Preeti,Srivastava,Kumar, Ashok
, p. 1729 - 1733 (2007/10/03)
A number of 5-substituted-N-[4′-(substitutedphenyl) aminomethyl-5′-(substitutedphenyl)isoxazolin-2′-yl]anthranilic acids have been synthesized by the Mannich reaction of 5-substituted-N-[5′-(substitutedphenyl)isoxazolin-2′-yl]anthranilic acids, which in turn is synthesized by the reaction of 5-substituted-N-chalconylanthranilic acids. In this series, compounds 9, 11, 15 and 18 show significant protection against carrageenan induced rat's paw oedema with lower ulcerogenic liability than phenylbutazone. The most active compound of this series is N-[5′-(m-methoxy, p-hydroxyphenyl)isoxazolin-2′-yl]anthranilic acid which has shown higher antiinflammatory activity and lower ulcerogenic property than phenylbutazone.
