362670-06-2

Basic information

• Product Name: tert-Butyl 5-fluoro-2-nitrophenylcarbamate
• Synonyms: tert-Butyl 5-fluoro-2-nitrophenylcarbamate;tert-butyl N-(5-fluoro-2-nitrophenyl)carbamate;(5-Fluoro-2-nitro-phenyl)-carbamic acid tert-butyl ester
• CAS NO: 362670-06-2
• Molecular Formula: C₁₁H₁₃FN₂O₄
• Molecular Weight: 256.2303232
• Mol File: 362670-06-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: tert-Butyl 5-fluoro-2-nitrophenylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl 5-fluoro-2-nitrophenylcarbamate(362670-06-2)
• EPA Substance Registry System: tert-Butyl 5-fluoro-2-nitrophenylcarbamate(362670-06-2)

Safety Data

• Hazardous Substances Data: 362670-06-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H13FN2O4/c1-11(2,3)18-10(15)13-8-6-7(12)4-5-9(8)14(16)17/h4-6H,1-3H3,(H,13,15)

Upstream product

• 320-98-9 5-fluoro-2-nitrobenzoic acid 
• 75-65-0 tert-butyl alcohol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 2369-11-1 5-fluoro-2-nitroaniline 

Downstream Products

• 362670-07-3 (2-amino-5-fluorophenyl)carbamic acid tert-butyl ester 
• 348133-45-9 6-fluoro-1-methyl-1,3-dihydro-2H-benzimidazol-2-one 
• 849236-19-7 tert-butyl 2-nitro-5-(thiophen-2-ylthio)phenylcarbamate 

Relevant articles and documents

HDAC DEGRADER

The disclosure provides compounds of formula (I). The compounds may be used to degrade the Histone Deacetylase (HDAC) family of enzymes, particularly HDAC1, 2 and 3 that exist in corepressor complexes. Accordingly, the compounds may

Phthalazine derivative, preparation method and applications thereof

The invention discloses a phthalazine derivative, a preparation method and applications thereof, and belongs to the field of medicinal chemistry, wherein the phthalazine derivative prepared by the invention is a good PARP and HDAC double-target inhibitor.

Design, synthesis and anticancer activities of novel dual poly(ADP-ribose) polymerase-1/histone deacetylase-1 inhibitors

Currently, synergistic inhibition of poly(ADP-ribose) polymerase-1 (PARP-1) and histone deacetylases (HDACs) has been a potential effective strategy for cancer treatment. Herein, by combining critical pharmacophores in approved drugs olaparib and chidamid

Design, synthesis and biological evaluation of novel human monoamine oxidase B inhibitors based on a fragment in an X-ray crystal structure

Herein we report our efforts of developing reversible selective hMAO-B inhibitors based on isatin, a fragment in an X-ray crystal structure. Five different scaffolds were designed and many compounds were synthesized. Among them, compound A3 demonstrated very high potency and isoform selectivity against hMAO-B, 11 and 13 times more potent (IC50 = 3 nM) and 23.64 and 6.8 times more selective than the marked drugs, selegiline and safinamide. However, the endeavors to modify the polar 3-one group of isatin, that is in a hydrophobic environment in the binding site of hMAO-B, to small nonpolar hydrophobic groups did not bring about improved hMAO-B inhibitors, which may challenge our understanding of molecular interactions and molecular recognition in biological systems.

1,3-dioxo-isoindoline benzamide compound and application thereof

The invention belongs to the technical field of diabetes treatment medicines and in particular relates to an N-(2-aminophenyl)-3-(1,3-dioxo-isoindoline-2-yl) benzamide compound, and a preparation andapplication thereof in preparing diabetes treatment medicines. The compound has a formula (1) shown in the description, in the formula, R is selected from hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl and tert-butyl, and X is selected from hydrogen or fluorine. The N-(2-aminophenyl)-3-(1,3-dioxo-isoindoline-2-yl) benzamide compound has a remarkable function of protecting pancreatic beta cells, and can be adopted to prepare novel diabetes treatment medicines.

HDAC3-SELECTIVE INHIBITORS

Disclosed herein are selective HDAC inhibitors. In some embodiments, the compounds are selective HDAC3 inhibitors. The compounds are useful to treat a variety of conditions, including cancers, i.e., breast cancer, cachexia, and liver steatosis.

HISTONE DEACETYLASE INHIBITORS

Provided herein are compounds and methods for inhibiting histone deacetylase ("HDAC") enzymes (e.g., HDAC1, HDAC2, and HDAC3).

Design, synthesis and biological screening of 2-aminobenzamides as selective HDAC3 inhibitors with promising anticancer effects

Histone deacetylases (HDACs) have been found as a potential target for anticancer therapy. A number of HDAC inhibitors have been used pre-clinically and clinically as anticancer agents. In the current study, we have designed and synthesized compound 12a by combining the scaffolds of CI-994 and BG45. Moreover, the structure of compound 12a was optimized and a series of 2-aminobenzamide derivatives were synthesized further. These compounds were tested for their HDAC inhibitory activity and found to be efficient HDAC inhibitors. Compound 26c showed 11.68-fold HDAC3 selectivity over pan HDACs, better than the prototype HDAC3 inhibitor BG45. Most of these compounds exhibited antiproliferative activity in both B16F10 and HeLa cell lines. Particularly, compound 26c exhibited better antitumor efficacy in the cell lines compared to the prototype inhibitors CI-994 and BG45. It was also found to promote apoptosis as well as induced significant cell growth arrest in the G2/M phase of cell cycle in B16F10 melanoma cells. This work may provide significant insight regarding structural information to design newer small molecule HDAC3 inhibitors to fight against the target specific malignancies in future.

Targeting breast cancer stem cells by novel HDAC3-selective inhibitors

Although histone deacetylase (HDAC) inhibitors have been known to suppress the cancer stem cell (CSC) population in multiple types of cancer cells, it remains unclear which HDAC isoforms and corresponding mechanisms contribute to this anti-CSC activity. Pursuant to our previous finding that HDAC8 regulates CSCs in triple-negative breast cancer (TNBC) cells by targeting Notch1 stability, we investigated related pathways and found HDAC3 to be mechanistically linked to CSC homeostasis by increasing β-catenin expression through the Akt/GSK3β pathway. Accordingly, we used a pan-HDAC inhibitor, AR-42 (1), as a scaffold to develop HDAC3-selective inhibitors, obtaining the proof-of-concept with 18 and 28. These two derivatives exhibited high potency and isoform selectivity in HDAC3 inhibition. Equally important, they showed in vitro and/or in vivo efficacy in suppressing the CSC subpopulation of TNBC cells via the downregulation of β-catenin.

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.