41859-57-8Relevant academic research and scientific papers
Amide Bond Formation via the Rearrangement of Nitrile Imines Derived from N-2-Nitrophenyl Hydrazonyl Bromides
Boyle, Mhairi,Livingstone, Keith,Henry, Martyn C.,Elwood, Jessica M. L.,Lopez-Fernandez, J. Daniel,Jamieson, Craig
supporting information, p. 334 - 338 (2022/01/20)
We report how the rearrangement of highly reactive nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides can be harnessed for the facile construction of amide bonds. This amidation reaction was found to be widely applicable to the synthesis of primary, secondary, and tertiary amides and was used as the key step in the synthesis of the lipid-lowering agent bezafibrate. The orthogonality and functional group tolerance of this approach was exemplified by the N-acylation of unprotected amino acids.
Tungsten-Catalyzed Transamidation of Tertiary Alkyl Amides
Feng, Fang-Fang,Liu, Xuan-Yu,Cheung, Chi Wai,Ma, Jun-An
, p. 7070 - 7079 (2021/06/30)
Transamidation has recently emerged as a straightforward and convenient means to diversify amides. However, the kinetically and thermodynamically demanding transamidation of notoriously robust, fully alkyl-substituted tertiary amides still remains a longstanding challenge. Here, we describe a method for the activation of tertiary alkyl amides to streamline transamidation using simple tungsten(VI) chloride as a catalyst and chlorotrimethylsilane as an additive. The highly electrophilic and oxophilic tungsten catalyst enables the selective scission of a C-N bond of tertiary alkyl amides to effect transamidation of a myriad of structurally and electronically diverse tertiary alkyl amides and amines. Mechanistic study implies that the synergistic effect of the catalyst and the additive could pronouncedly induce the nucleophilic acyl substitution of tertiary alkyl amide with amine to realize transamidation.
Bezafibrate scaffold derived hydrazide-hydrazones: Synthesis and antioxidant activities
Pallapati, Ramya Krishna,Gugulothu, Sailaja,Vanga, Umamaheswara Rao,Bollikolla, Hari Babu
, p. 2473 - 2482 (2020/09/09)
A NEW series of Bezafibrate derived hydrazide-hydrazone analogues were generated by using some five membered, fused heterocyclic and aromatic aldehydes. All the hydrazones were obtained in good yields from methanol at 60-80°C for 5-8 hours stirring. Moreover, the compounds were also screened for their anti-oxidant activity potentiality at four different concentrations using DPPH method. Among these compounds, compound 6k analogue of bezafibrate was found to be the most active at all the tested concentrations (≈ 40% inhibition at 25 μg/mL ) followed by 6j (4-hydroxy, 3-methoxy 5-bromo analogue ≈ 35% at 25 μg/mL) compared to standard ascorbic acid (49.6% at 25 μg/mL).
Spirooxazoline Synthesis by an Oxidative Dearomatizing Cyclization
Tariq, M. Umair,Moran, Wesley J.
, p. 5153 - 5160 (2020/07/30)
Spirocyclic compounds are of increasing importance owing to their potential applications in the development of new pharmaceuticals. Herein, we describe a new, rapid access to rarely seen spirooxazolines utilizing an I(I)/I(III) reaction manifold. The scope of the cyclization using phenols and naphthols is described along with the stereoselective functionalization of the spirocycles. The application of this method to the formation of dihydrooxazines is also demonstrated.
Design and Scalable Synthesis of N-Alkylhydroxylamine Reagents for the Direct Iron-Catalyzed Installation of Medicinally Relevant Amines**
Delcaillau, Tristan,Falk, Eric,Gürtler, Laura,Makai, Szabolcs,Morandi, Bill
supporting information, p. 21064 - 21071 (2020/09/21)
Secondary and tertiary alkylamines are privileged substance classes that are often found in pharmaceuticals and other biologically active small molecules. Herein, we report their direct synthesis from alkenes through an aminative difunctionalization reaction enabled by iron catalysis. A family of ten novel hydroxylamine-derived aminating reagents were designed for the installation of several medicinally relevant amine groups, such as methylamine, morpholine and piperazine, through the aminochlorination of alkenes. The method has excellent functional group tolerance and a broad scope of alkenes was converted to the corresponding products, including several drug-like molecules. Besides aminochlorination, the installation of other functionalities through aminoazidation, aminohydroxylation and even intramolecular carboamination reactions, was demonstrated, further highlighting the broad potential of these new reagents for the discovery of novel amination reactions.
Preparation process of bezafibrate compound
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Paragraph 0060-0062, (2018/10/19)
The invention especially relates to preparation technology for a bezafibrate compound, belonging to the field of pharmaceutical synthesis. The invention provides a preparation process of the bezafibrate compound. The preparation process comprises the following steps: subjecting a compound with a structure as shown in a formula a or a' and a compound with a structure as shown in a formula b to an acylation reaction in an aqueous solution of inorganic base B so as to obtain a bezafibrate intermediate with a structure as shown in a formula c; and then subjecting the bezafibrate intermediate, R1COR2 and methyl halide to a condensation reaction in an aqueous solution of inorganic alkali A to obtain the bezafibrate compound with a structure as shown in a formula d, wherein process flow is as described in the specification, M is a water-soluble inorganic acid, X is a halogen or alkoxy group, and R1 and R2 are the same or different and are selected from a group consisting of H and C1-C3 alkylgroups.
Structure-activity relationships and cancer-cell selective toxicity of novel inhibitors of glioma-associated oncogene homologue 1 (Gli1) mediated transcription
Mahindroo, Neeraj,Connelly, Michele C.,Punchihewa, Chandanamali,Kimura, Hiromichi,Smeltzer, Matthew P.,Wu, Song,Fujii, Naoaki
experimental part, p. 4277 - 4287 (2010/03/01)
We report novel inhibitors of Gli1-mediated transcription as potential anticancer agents. Focused chemical libraries were designed and assessed for inhibition of functional cell-based Gli1-mediated transcription and selective toxicity toward cancer cells. The SAR was revealed, and the selectivity of the lead compounds' inhibition of Gli1-mediated transcription over that of Gli2 was determined. Compound 63 (NMDA298-1), which inhibited Gli1-mediated transcription in C3H10T1/2 cells with an IC50 of 6.9 μM, showed 3-fold selectivity for inhibiting transcription mediated by Gli1 over that by Gli2. Cell-viability assays were performed to evaluate the chemical library in a normal cell line and a panel of cancer cell lines with or without up-regulated expression of the Gli1 gene. These compounds decreased the viability of several cancer cell lines but were less active in the noncancerous BJ-hTERT cells. 2009 American Chemical Society.
