3663-81-8

Usage

Uses

Used in Pharmaceutical Industry:
2,3-DIHYDRO-1,4-BENZODIOXINE-2-CARBONYL CHLORIDE is used as a key intermediate for the synthesis of various pharmaceutical compounds. Its ability to introduce carbonyl groups into organic molecules is essential in the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 2,3-DIHYDRO-1,4-BENZODIOXINE-2-CARBONYL CHLORIDE is utilized as a reagent in the production of agrochemicals. Its role in creating carbonyl-containing molecules aids in the development of effective pesticides and other agricultural chemicals.
Used in Fine Chemicals Industry:
2,3-DIHYDRO-1,4-BENZODIOXINE-2-CARBONYL CHLORIDE is employed as a building block in the synthesis of fine chemicals. Its versatility in organic synthesis allows for the creation of a wide range of specialty chemicals used in various applications, including fragrances, dyes, and other high-value products.
Used in Organic Synthesis Research:
As a reagent in organic synthesis, 2,3-DIHYDRO-1,4-BENZODIOXINE-2-CARBONYL CHLORIDE is used in research settings to explore new chemical reactions and pathways. Its capacity to introduce carbonyl groups is valuable for understanding and advancing the field of organic chemistry.

InChI:InChI=1/C9H7ClO3/c10-9(11)8-5-12-6-3-1-2-4-7(6)13-8/h1-4,8H,5H2

Upstream product

• 4739-94-0 ethyl 2,3-dihydro-1,4-benzodioxin-2-carboxylate 
• 3663-79-4 methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate 
• 3663-80-7 1,4-benzodioxane-2-carboxylic acid 

Downstream Products

• 617677-53-9 1,4-bis-(2,3-dihydro-benzo[1,4]dioxin-2-carbonyl)-piperazine 
• 84541-68-4 N-[(4-hydroxy-2-isopropyl-5-methyl)-phenoxyethyl]-N-methyl-[2-(1,4-benzodioxane)]methylamine 
• 21398-80-1 N-methyl-2,3-dihydrobenzo[b][1,4]dioxine-2-carboxamide 

Relevant academic research and scientific papers

Synthesis of a new doxazosin-related compound

A simple procedure for the synthesis of 1-[4-(2,3-dihydro-1, 4-benzodioxin-2-yl) amide-6, 7-dimethoxy-2-quazolinyl]-4-(1,4-bensodioxan-2-yl- carbonyl) piperazine is described. Copyright Taylor & Francis Group, LLC.

Computer-aided discovery of phenylpyrazole based amides as potent S6K1 inhibitors

Ribosomal protein S6 kinase beta-1 (S6K1) is an attractive therapeutic target. In this study, computational analysis of five thiophene urea-based S6K1 inhibitors was performed. Molecular docking showed that the five compounds formed hydrogen bonds with residues Glu173 and Leu175 of S6K1 and hydrophobic interactions with residues Val105, Leu97 and Met225, and these interactions were key elements for the inhibitory potency of the compounds. Binding free energy (?Gbind) decomposition analysis showed that Leu97, Glu173, Val 105, Leu175, Leu97 and Met225 contribute the most to ?Gbind. Based on the computer results, phenylpyrazole based amides (D1-D3) were designed and synthesized. Biological evaluation revealed thatD2exhibited 15.9 nM S6K1 inhibition, medium microsomal stability and desirable bioavailability.

Selective α-Oxyamination and Hydroxylation of Aliphatic Amides

Compared to the α-functionalization of aldehydes, ketones, even esters, the direct α-modification of amides is still a challenge because of the low acidity of α-CH groups. The α-functionalization of N?H (primary and secondary) amides, containing both an unactived α-C?H bond and a competitively active N?H bond, remains elusive. Shown herein is the general and efficient oxidative α-oxyamination and hydroxylation of aliphatic amides including secondary N?H amides. This transition-metal-free chemistry with high chemoselectivity provides an efficient approach to α-hydroxy amides. This oxidative protocol significantly enables the selective functionalization of inert α-C?H bonds with the complete preservation of active N?H bond.

Regio- and stereoselective Pd-catalyzed direct arylation of unactivated sp3 C(3)-H bonds of tetrahydrofuran and 1,4-benzodioxane systems

An auxiliary-enabled Pd-catalyzed highly regio- and stereoselective sp3 C-H activation and the direct arylation of the C3-position of oxygen heterocycles, such as tetrahydrofuran and 1,4-benzodioxane systems, are reported. An efficient stereoselective construction of cis 2,3-disubstituted tetrahydrofuran derivatives (analogues of norlignans) and cis 2,3-disubstituted 1,4-benzodioxane derivatives (analogues of neolignans) is described. The direct C(sp3)-H arylation of the C3-position of (R)- or (S)- tetrahydrofuran-2-carboxamides furnished the corresponding (2R,3R) and (2S,3S) C3-arylated THF scaffolds as major compounds with very high regio- and diastereoselectivities. The stereochemistry of the products obtained in this work were unambiguously assigned on the basis of the X-ray structure analyses of representative compounds 3b, 3e, 4p, and 7.

Synthesis and biological evaluation of a series of benzoxazole/ benzothiazole-containing 2,3-dihydrobenzo[b][1,4]dioxine derivatives as potential antidepressants

A series of benzoxazole/benzothiazole-2,3-dihydrobenzo[b][1,4]dioxine derivatives (5a-5d and 8a-8j) was synthesized. Compounds were evaluated for binding affinities at the 5-HT1A and 5-HT2A receptors. Antidepressant activities of the compounds were screened using the forced swimming test (FST) and the tail suspension test (TST). The results indicated that the compounds exhibited high affinities for the 5-HT1A and 5-HT2A receptors and showed a marked antidepressant-like activity. Compound 8g exhibited high affinities for the 5-HT1A (Ki = 17 nM) and 5-HT2A (Ki = 0.71 nM) receptors; it also produced a decrease of the immobility time and exhibited potent antidepressant-like effects in the FST and TST in mice.

NITROGEN-CONTAINING FUSED RING COMPOUNDS FOR USE AS CRTH2 ANTAGONISTS

The present application relates to nitrogen-containing fused ring compounds shown by general formula (I), a pharmaceutically acceptable salt thereof and a stereoisomer thereof as CRTH2 antagonist, wherein X1, X2, X3, X4, X5, W, X, Y, L1, L2, L3, A, B are as defined in the description; the present application further relates to a method for preparing the compounds, a pharmaceutical formulation and a pharmaceutical composition comprising the compounds, a use of the compounds for the manufacture of a medicament for the treatment and/or prevention of diseases related to activity of CRTH2.

NITROGEN-CONTAINING FUSED RING COMPOUNDS AS CRTH2 ANTAGONISTS

The present application relates to nitrogen-containing fused ring compounds shown by general formula (I), a pharmaceutically acceptable salt thereof and a stereoisomer thereof as CRTH2 antagonist, wherein X1, X2, X3, X4, X5, W, X, Y, L1, L2, L3, A, B are as defined in the description; the present application further relates to a method for preparing the compounds, a pharmaceutical formulation and a pharmaceutical composition comprising the compounds, a use of the compounds for the manufacture of a medicament for the treatment and/or prevention of diseases related to activity of CRTH2.

Synthesis of diamides from 1,4-Benzodioxane-2-and isochroman-1-carboxylic acids

1,4-Benzodioxane-2-carboxylic acid and isochroman-1-carboxylic acid were treated with thionyl chloride, and the resulting acid chlorides reacted with p-aminobenzoic acid in dioxane in the presence of pyridine to produce the corresponding amido acids. The

Discovery of 6-substituted 4-anilinoquinazolines with dioxygenated rings as novel EGFR tyrosine kinase inhibitors

It had been reported that some dioxygenated rings fusing with the quinazoline scaffold could lead to new EGFR inhibitors. Based on this, several kinds of oxygenated alkane quinazoline derivatives were synthetized and evaluated as EGFR inhibitors. Their antiproliferative activities were tested against four cancer cell lines: A431, MCF-7, A549, and B16-F10. Most derivatives could counteract EGF-induced EGFR phosphorylation, and their potency was comparable to the reference compound Erlotinib. The size of the fused dioxygenated ring was crucial for the biological activity and the heptatomic ring derivative 19 showed potent in vitro inhibitory activity in the enzymatic assay as well as in the cellular assay.

QUINAZOLINE DERIVATIVES AS KINASE INHIBITORS

The invention is directed to quinazoline compounds that can inhibit the bioactivity of one or more kinase enzymes, including a Rho kinase, an AKT kinase, a p70S6K kinase, a LIM kinase, an IKK kinase, a Fit kinase, an Aurora kinase, or a Src kinase, or any combination thereof; to methods of use of those compounds; and to methods of preparation of those compounds. The inventive compounds can be used in the treatment of malconditions including cardiovascular disease, neurogenic pain, hypertension, atherosclerosis, angina, stroke, arterial obstruction, peripheral arterial disease, erectile dysfunction, acute and chronic pain, dementia, Alzheimer's disease, Parkinson's disease, neuronal degeneration, asthma, amyotrophic lateral sclerosis, spinal cord injury, rheumatoid arthritis, osteoarthritis, osteoporosis, psoriasis, cerebral vasospasm, open angle glaucoma, multiple sclerosis, pulmonary hypertension, acute respiratory distress syndrome, inflammation, diabetes, urinary organ diseases and benign prostatic hypertrophy (BPH), metastasis, cancer, glaucoma, ocular hypertension, retinopathy, autoimmune disease, viral infection, or myocardial pathology.