335254-77-8

Usage

Uses

Used in Pharmaceutical Industry:
N-(3-Nitro[1,1'-biphenyl]-4-yl)carbamic Acid tert-Butyl Ester is used as a reactant for the optimization and preparation of selective HDAC1/HDAC2 inhibitors. These inhibitors play a crucial role in the development of targeted therapies for various diseases, including cancer, by modulating the activity of histone deacetylases (HDACs), which are enzymes involved in the regulation of gene expression.

Upstream product

• 335254-69-8 1-(tert-butoxycarbonyl)amino-4-iodo-2-nitrobenzene 
• 98-80-6 phenylboronic acid 
• 327046-79-7 tert-butyl (4-bromo-2-nitrophenyl)carbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 875-51-4 4-Bromo-2-nitroaniline 

Downstream Products

• 958007-07-3 ethyl (1'-{5-[({4-[(t-butoxycarbonyl)amino]biphenyl-3-yl}amino)carbonyl]pyridin-2-yl}-2,3-dihydro-1'H-spiro[indene-1,4'-piperidin]-3-yl)carbamate 
• 1003316-12-8 tert-butyl (3-(4-(aminomethyl)benzamido)-[1,1'-biphenyl]-4-yl)carbamate 
• 937728-81-9 t-butyl {3-[(6-chloropyridine-3-carbonyl)amino][1,1'-biphenyl]-4-yl}carbamate 
• 335255-33-9 tert-butyl (3-amino-4-biphenylyl)carbamate 

Relevant academic research and scientific papers

Balancing Histone Deacetylase (HDAC) Inhibition and Drug-likeness: Biological and Physicochemical Evaluation of Class?I Selective HDAC Inhibitors

Herein we report the structure-activity and structure-physicochemical property relationships of a series of class I selective ortho-aminoanilides targeting the “foot-pocket” in HDAC1&2. To balance the structural benefits and the physicochemical disadvantages of these substances, we started with a set of HDACi related to tacedinaline (CI-994) and evaluated their solubility, lipophilicity (log D7.4) and inhibition of selected HDAC isoforms. Subsequently, we selected the most promising “capless” HDACi and transferred its ZBG to our previously published scaffold featuring a peptoid-based cap group. The resulting hit compound 10 c (LSH-A54) showed favorable physicochemical properties and is a potent, selective HDAC1/2 inhibitor. The following evaluation of its slow binding properties revealed that LSH-A54 binds tightly to HDAC1 in an induced-fit mechanism. The potent HDAC1/2 inhibitory properties were reflected by attenuated cell migration in a modified wound healing assay and reduced cell viability in a clonogenic survival assay in selected breast cancer cell lines.

Design and Synthesis of Novel N-(2-aminophenyl)benzamide Derivatives as Histone Deacetylase Inhibitors and Their Antitumor Activity Study

Histone deacetylases (HDACs) are promising therapeutic targets for cancer therapy because inhibition of HDACs triggers growth arrest or apoptosis of tumor cells. In the present study, a new series of fluorinated N-(2-aminophenyl)benzamide derivatives were synthesized to investigate potential inhibition of HDACs and associated anticancer activity. Among the synthesized derivatives, compound 24a showed potent inhibitory activity of HDACs and higher antitumor efficacy in human cancer cell lines (HCT-116, MCF-7, and A549) compared with SAHA. Moreover, animal studies demonstrated that compound 24a showed potent in vivo antitumor efficacy in an HCT-116 colon cancer xenograft mouse model.

URSODEOXYCHOLIC ACID DERIVATIVES FOR THE TREATMENT OF POLYCYSTIC DISEASES

The present invention relates to compounds derived from ursodeoxycholic acid of formula (I), to methods for obtaining same, as well as the use thereof in the treatment of polycystic diseases, particularly autosomal dominant polycystic liver disease, autos

Selective HDAC inhibitors with potent oral activity against leukemia and colorectal cancer: Design, structure-activity relationship and anti-tumor activity study

Previously, we reported the discovery of a series of N-hydroxycinnamamide-based HDAC inhibitors, among which compound 11y exhibited high HDAC1/3 selectivity. In this current study, structural derivatization of 11y led to a new series of benzamide based HDAC inhibitors. Most of the compounds exhibited high HDACs inhibitory potency. Compound 11a (with 4-methoxybenzoyl as N-substituent in the cap and 4-(aminomethyl) benzoyl as the linker group) exhibited selectivity against HDAC1 to some extent, and showed potent antiproliferative activity against several tumor cell lines. In?vivo studies revealed that compound 11a displayed potent oral antitumor activity in both hematological tumor cell U937 xenograft model and solid tumor cell HCT116 xenograft model with no obvious toxicity. Further modification of benzamide 3, 11a and 19 afforded new thienyl and phenyl compounds (50a, 50b, 63a, 63b and 63c) with dramatic HDAC1 and HDAC2 dual selectivity, and the fluorine containing compound 56, with moderate HDAC3 selectivity.

Design, synthesis and anti-tumor activity study of novel histone deacetylase inhibitors containing isatin-based caps and o-phenylenediamine-based zinc binding groups

As a hot topic of epigenetic studies, histone deacetylases (HDACs) are related to lots of diseases, especially cancer. Further researches indicated that different HDAC isoforms played various roles in a wide range of tumor types. Herein a novel series of HDAC inhibitors with isatin-based caps and o-phenylenediamine-based zinc binding groups have been designed and synthesized through scaffold hopping strategy. Among these compounds, the most potent compound 9n exhibited similar if not better HDAC inhibition and antiproliferative activities against multiple tumor cell lines compared with the positive control entinostat (MS-275). Additionally, compared with MS-275 (IC50 values for HDAC1, 2 and 3 were 0.163, 0.396 and 0.605?μM, respectively), compound 9n with IC50 values of 0.032, 0.256 and 0.311?μM for HDAC1, 2 and 3 respectively, showed a moderate HDAC1 selectivity.

Kinetic and structural insights into the binding of histone deacetylase 1 and 2 (HDAC1, 2) inhibitors

The structure–activity and structure–kinetic relationships of a series of novel and selective ortho-aminoanilide inhibitors of histone deacetylases (HDACs) 1 and 2 are described. Different kinetic and thermodynamic selectivity profiles were obtained by va

PHOTOSWITCHABLE HDAC INHIBITORS

This invention relates to photoswitchable inhibitors of histone deacetylases and methods of using the same. Provided herein are inhibitors of HDAC having photoswitchable modulators of protein function with short thermal relaxation kinetics. The compounds

Delayed and prolonged histone hyperacetylation with a selective HDAC1/HDAC2 inhibitor

The identification and in vitro and in vivo characterization of a potent SHI-1:2 are described. Kinetic analysis indicated that biaryl inhibitors exhibit slow binding kinetics in isolated HDAC1 and HDAC2 preparations. Delayed histone hyperacetylation and

SUBSTITUTED NICOTINAMIDE COMPOUNDS

The present invention relates to a novel class of substituted nicotinamides. These compounds can inhibit histone deacetylase and are suitable for use in selectively inducing terminal differentiation, and arresting cell growth and/or apoptosis of neoplasti

Fluorescent compounds that bind to histone deacetylase

The present invention relates to a novel class of fluorescent compounds that bind to histone deacetylases. The fluorescent compounds can be used to determine binding association and dissociation rates of histone deacetylase inhibitors via fluorescence polarization.