37682-31-8

Upstream product

• 64-17-5 ethanol 
• 1878-87-1 2-nitrophenoxyacetic acid 
• 20142-87-4 2-(2-nitrophenoxy)acetyl chloride 
• 824-39-5 sodium o-nitrophenate 
• 105-39-5 chloroacetic acid ethyl ester 
• 105-36-2 ethyl bromoacetate 
• 88-75-5 2-hydroxynitrobenzene 
• 5735-53-5 1,4-benzoxazine 
• 824-38-4 potassium 2-nitrophenoxide 

Downstream Products

• 27320-99-6 3,4-dihydro-7-chloro-3-oxo-2H-1,4-benzoxazine 
• 1878-87-1 2-nitrophenoxyacetic acid 
• 116977-28-7 2-(2-nitrophenoxy)acetohydroxamic acid 
• 16365-25-6 2-(2-hydroxyethoxy)nitrobenzene 
• 5466-88-6 3,4-dihydro-3-oxo-2H-1,4-benzoxazine 
• 5023-12-1 6-methoxy-2H-benzo[b][1,4]oxazin-3(4H)-one 
• 67193-97-9 7-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one 
• 7652-29-1 6-chloro-2H-1,4-benzoxazin-3(4H)-one 
• 53412-38-7 6-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-3-one 
• 1263183-83-0 C₁₃H₁₀N₄O₄S 
• 1263183-97-6 C₉H₁₀N₄O₄S 
• 77729-22-7 (2-nitro-phenoxy)-acetic acid hydrazide 
• 1342235-17-9 6-(1-(3,5-dichlorophenyl)-4-phenyl-1H-pyrazol-3-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one 
• 1086390-21-7 6-(2-(3-methylphenyl)acetyl)-2H-benzo[b][1,4]oxazin-3(4H)-one 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of oxime lacking Psammaplin inspired chemical libraries as anti-cancer agents

In this study, we attempted the chemical simplification of Psammaplin (PsA), while retaining its activity in vitro. Inspired by the previous Structure Activity Relationship (SAR) studies on various PsA analogues and relying on the fact that oxime is metabolically unstable, we initially designed and synthesized a diverse library of PsA analogues and evaluated for cytotoxic activity. Among 32 compounds of Psammaplin analogues synthesized, the compound 10b was almost equally active as parent Psammaplin in vitro.

Synthesis and antimicrobial activity of some benzoxazinoids derivatives of 2-nitrophenol and 3-hydroxy-2-nitropyridine

Benzoxazinoids (BXs), alkaloids frequently found in Gramineae species, are natural defensives that can potentially be exploited to the development of novel antimicrobial agents. Here, BXs analogs were synthesized from 2-nitrophenol (benzoxazinone series)

Deconstructive di-functionalization of unstrained, benzo cyclic amines by C-N bond cleavage using a recyclable tungsten catalyst

With H2WO4 as the catalyst and H2O2 as the oxidant, we herein report a deconstructive difunctionalization of the C-N bond in unstrained, benzo cyclic amines to generate an ester group and nitro group simultaneously. The preliminary mechanistic studies suggested that the corresponding hydroxamic acid is the key intermediate for this transformation. Importantly, with the utilization of this transformation, we achieved an interesting approach for the ring contraction of quinoline to indole, an example of scaffold hopping in a hetero-aromatic system.

Aryne Trifunctionalization Enabled by 3-Silylaryne as a 1,2-Benzdiyne Equivalent

An unprecedented aryne 1,2,3-trifunctionalization protocol from 2,6-bis(silyl)aryl triflates was developed under transition-metal-free conditions. The reaction of generated 3-silylaryne with both pyridine N-oxide and N-hydroxylamide afforded o-silyl triflate/tosylate in a one-pot transformation, allowing the formation of 2,3-aryne precursors with various vicinal pyridinyl/amido substituents. These pyridinyl-substituted 2,3-aryne intermediates exhibit a broad scope of reactivity with diverse arynophiles in good yields and high selectivity.

The synthesis and evaluation of phenoxyacylhydroxamic acids as potential agents for Helicobacter pylori infections

Two series of ω-phenoxy contained acylhydroxamic acids as novel urease inhibitors were designed and synthesized. Biological activity evaluations revealed that ω-phenoxypropinoylhydroxamic acids were more active than phenoxyacetohydroxamic acids. Out of these compounds, 3-(3,4-dichlorophenoxy)propionylhydroxamic acid c24 showed significant potency against urease in both cell free extract (IC50 = 0.061 ± 0.003 μM) and intact cell (IC50 = 0.89 ± 0.05 μM), being over 450- and 120-fold more potent than the clinically prescribed urease inhibitor AHA, repectively. Non-linear fitting of experimental data (V-[S]) suggested a mixed-type inhibition mechanism and a dual site binding mode of these compounds.

Heterocyclic substituted styrene compound and use thereof

The invention relates to a heterocyclic substituted styrene compound and its use. The invention discloses a heterocyclic radical, alkoxy and halogen modified styrene compound. Results of inhibition activity of the compound against Syk (spleen tyrosine kinase) show that the compound has inhibition activity against the Syk (spleen tyrosine kinase), and part of the compound has stronger inhibition activity against the Syk, and a structure foundation for further design and development of new Syk inhibitor-class rheumatoid arthritis (RA) therapy drugs is laid.

Identification of the novel N-phenylbenzenesulfonamide derivatives as potent HIV inhibitors

Searching for more safe and effective agents for HIV treatments is still an urgent topic worldwide. Based on our continuous modifications on the benzophenone derivatives as HIV-1 reverse transcriptase (RT) inhibitors, a new template bearing N-phenylbenzenesulfonamide (PBSA) structure was designed to enhance the interactions with HIV-1 RT. In this manuscript, a series of PBSA derivatives were synthesized and evaluated for their anti-HIV-1 activity. The preliminary test showed that these compounds were potent to inhibit wild-type HIV-1 with EC50 values ranging of 0.105-14.531 μmol/L. In particular, compound 13f not only has high anti-HIV-1 activity (0.108 μmol/L), but also possesses low toxicity with a TI value of 1816.6. Furthermore, the major interactions of the inhibitor 13f with HIV-1 RT were also investigated using the molecular modelling. Our discovered structure-activity relationships (SARs) of these analogues may serve as an important clue for further optimizations.

H3PO4/(CF3CO)2O mediated acylation followed by hurd-mori reaction: Synthesis of novel 1,2,3-thiadiazol derivatives

The synthesis of novel 1,2,3-thiadiazol derivatives containing 2H-benzo[b][1,4]oxazin-3(4H)-one moiety as one of the substituents has been reported. A combined application of H3PO4/(CF 3CO)2O mediated acylation followed by Hurd-Mori reaction has been explored to synthesize these compounds. The scope and limitation of this strategy along with the reaction mechanism of the key step is discussed.

Synthesis and pharmacological evaluations of novel 2H-benzo[b][1,4]oxazin- 3(4H)-one derivatives as a new class of anti-cancer agents

The synthesis of novel 2H-benzo[b][1,4]oxazin-3(4H)-one derivatives has been carried out using trifluoroacetic anhydride/phosphoric acid mediated C-C bond forming reaction as a key step. This method does not require the use of environmentally harmful AlCl3 or moisture sensitive acid chloride. A number of compounds containing the benzooxazinone moiety attached to a five-membered central heterocyclic ring was synthesized and tested for their anti-cancer properties in vitro against three cell lines e.g. A549 (lung), DLD-1 (colorectal adenocarcinoma) and MV4-11 (acute myeloid leukemia). Some of them showed anti-cancer activities along with a number of reference compounds tested. Few of them showed promising anti-leukemic properties. A brief Structure-Activity-Relationship study within the series is presented. An imidazole derivative 9c containing benzene ring with a para-CF3 group at C-2 position was identified as a potent anti-leukemic agent.

Synthesis and xanthine oxidase inhibitory activity of 7-methyl-2- (phenoxymethyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one derivatives

An elevated level of blood uric acid (hyperuricemia) is the underlying cause of gout. Xanthine oxidase is the key enzyme that catalyzes the oxidation of hypoxanthine to xanthine and then to uric acid. Allopurinol, a widely used xanthine oxidase inhibitor is the most commonly used drug to treat gout. However, a small but significant portion of the population suffers from adverse effects of allopurinol that includes gastrointestinal upset, skin rashes and hypersensitivity reactions. Moreover, an elevated level of uric acid is considered as an independent risk factor for cardiovascular diseases. Therefore use of allopurinol-like drugs with minimum side effects is the ideal drug of choice against gout. In this study, we report the synthesis of a series of pyrimidin-5-one analogues as effective and a new class of xanthine oxidase inhibitors. All the synthesized pyrimidin-5-one analogues are characterized by spectroscopic techniques and elemental analysis. Four (6a, 6b, 6d and 6f) out of 20 synthesized molecules in this class showed good inhibition against three different sources of xanthine oxidase, which were more potent than allopurinol based on their respective IC50 values. Molecular modeling and docking studies revealed that the molecule 6a has very good interactions with the Molybdenum-Oxygen-Sulfur (MOS) complex a key component in xanthine oxidase. These results highlight the identification of a new class of xanthine oxidase inhibitors that have potential to be more efficacious, than allopurinol, to treat gout and possibly against cardiovascular diseases.