104478-97-9Relevant articles and documents
Amide compound and derivative thereof, preparation method, pharmaceutical composition and application thereof
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Paragraph 0081; 0082; 0085; 0086, (2021/07/09)
The invention discloses an amide compound and derivative thereof, a preparation method, a pharmaceutical composition and application thereof. The structure of the amide compound is shown as a formula (I). The derivatives of theamide compound relate to a stereoisomer, a tautomer, a metabolite, a metabolic precursor, a prodrug, a solvate, a salt of the solvate, a crystal, a pharmaceutically acceptable salt or a mixture of the above of theamide compound. The amide compound and the derivative thereof have an efficient inhibition effect on indoleamine 2, 3-dioxygenase 1, and can be used for preparing medicines for treating indoleamine 2, 3-dioxygenase 1 mediated immunosuppression related diseases, the prepared medicine can exert the medicine effect at the molecular level and is wide in application, and the synthesis method of the compound is simple, convenient and easy to operate.
Reversible small molecule inhibitors of MAO A and MAO B with anilide motifs
Grau, Kathrin,Hagenow, Jens,Hagenow, Stefanie,Hefke, Lena,Khanfar, Mohammad,Proschak, Ewgenij,Stark, Holger
, p. 371 - 393 (2020/02/11)
Background: Ligands consisting of two aryl moieties connected via a short spacer were shown to be potent inhibitors of monoamine oxidases (MAO) A and B, which are known as suitable targets in treatment of neurological diseases. Based on this general blueprint, we synthesized a series of 66 small aromatic amide derivatives as novel MAO A/B inhibitors. Methods: The compounds were synthesized, purified and structurally confirmed by spectroscopic methods. Fluorimetric enzymological assays were performed to determine MAO A/B inhibition properties. Mode and reversibility of inhibition was determined for the most potent MAO B inhibitor. Docking poses and pharmacophore models were generated to confirm the in vitro results. Results: N-(2,4-Dinitrophenyl)benzo[d][1,3]dioxole-5-carboxamide (55, ST-2043) was found to be a reversible competitive moderately selective MAO B inhibitor (IC50 = 56 nM, Ki = 6.3 nM), while N-(2,4-dinitrophenyl)benzamide (7, ST-2023) showed higher preference for MAO A (IC50 = 126 nM). Computational analysis confirmed in vitro binding properties, where the anilides examined possessed high surface complementarity to MAO A/B active sites. Conclusion: The small molecule anilides with different substitution patterns were identified as potent MAO A/B inhibitors, which were active in nanomolar concentrations ranges. These small and easily accessible molecules are promising motifs, especially for newly designed multitargeted ligands taking advantage of these fragments.
Synthesis of benzothiazoles via ipso substitution of ortho- methoxythiobenzamides
Downer, Nadale K.,Jackson, Yvette A.
, p. 3039 - 3043 (2007/10/03)
An efficient route to the synthesis of benzothiazoles from orthoo-methoxythiobenzamides via the ipso substitution of an aromatic methoxy group is presented, and the mechanism of the Jacobson synthesis of benzothiazoles is further investigated.
Quinone Imine Route to Benzimidazol-2-ylcarbamates. Part 1. Synthesis of Open-chain and Cyclic 5-Acylamino Derivatives.
Rajappa, Srinivasachari,Sreenivasan, Ramaswami,Khalwadekar, Asha
, p. 1657 - 1675 (2007/10/02)
The synthesis of the N',N''-bismethoxycarbonyl-N-(4-acylaminophenyl)guanidines (4) and (7) is described.Oxidation of these with LTA has led to the benzimidazol-2-ylcarbamates. (8), (9) and (10) through a regiospecific cyclisation of quinone imine intermediates.If the acylamino group is part of a ring, the yield of benzimidazoles (15) increases with the size of the lactam ring.The direction of ring closure may be controlled by electronic and steric factors.
