35700-40-4

Usage

Uses

Used in Organic Synthesis:
2,3-Dihydrobenzofuran-7-carboxylic acid is used as a building block in organic synthesis for its ability to form various chemical compounds through reactions. Its versatile structure allows for the creation of a wide range of molecules with potential applications in different fields.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2,3-dihydrobenzofuran-7-carboxylic acid is used as a key intermediate in the development of new drugs. Its unique structure and functional groups make it a promising candidate for the synthesis of bioactive molecules with potential therapeutic effects.
Used in Drug Development:
2,3-Dihydrobenzofuran-7-carboxylic acid is utilized in the development of new drugs due to its potential to interact with biological targets. Its carboxylic acid functional group can form hydrogen bonds and coordinate with metal ions, making it suitable for the design of molecules with specific binding properties.
Used in Material Science:
2,3-DIHYDROBENZOFURAN-7-CARBOXYLIC ACID's structure and properties also make it a valuable tool in the field of material science. It can be used to develop new materials with unique properties, such as improved stability, reactivity, or selectivity in various applications.
Used in Chemical Reaction Studies:
2,3-Dihydrobenzofuran-7-carboxylic acid is employed in the study of chemical reactions to understand its reactivity and the mechanisms involved. This knowledge can be applied to optimize reaction conditions and develop more efficient synthetic routes.
Used in Biological Process Research:
2,3-DIHYDROBENZOFURAN-7-CARBOXYLIC ACID's potential interactions with biological systems make it a valuable tool in the study of biological processes. It can be used to investigate the mechanisms of action, binding affinities, and potential applications in therapeutic interventions.

Upstream product

• 133844-95-8 2,3-dihydro-benzofuran-7-carboxylic acid methyl ester 
• 6282-42-4 methyl 2-allyloxybenzoate 
• 496-16-2 2.3-dihydrobenzofuran 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 124-38-9 carbon dioxide 
• 31456-98-1 methyl 3-allyl-salicylate 
• 75934-11-1 2-<2-Methoxy-3-(2-hydroxyethyl)phenyl>-4,4-dimethyl-2-oxazoline 
• 75934-03-1 2-<2-Methoxy-2-(formylmethyl)phenyl>-4,4-dimethyl-2-oxazoline 
• 75934-02-0 2-(3-allyl-2-methoxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole 
• 75934-00-8 2-Allyl-6-(carbomethoxy)anisole 
• 75934-01-9 2-Methoxy-3-allylbenzoic Acid 
• 119-36-8 methyl salicylate 
• 69-72-7 salicylic acid 
• 75855-24-2 2-Hydroxy-3-vinyl-benzoic acid methyl ester 

Downstream Products

• 13414-56-7 2,3-dihydrobenzo[b]furan-7-ylamine 
• 170730-06-0 1-(2,3-dihydrobenzofuran-7-yl)ethanone 
• 134401-97-1 2,3-dihydrobenzofuran-7-carboxamide 
• 1616110-67-8 methyl 5-amino-2,3-dihydrobenzofuran-7-carboxylate 
• 1037758-74-9 6-(2,5-difluorobenzyl)-N-(methylsulfonyl)-8-(2-oxo-1,2-dihydropyridin-3-yl)-3,6-dihydro-2H-furo[2,3-e]indole-7-carboxamide 
• 1037763-79-3 6-(2,5-difluorobenzyl)-8-(2-methoxypyridin-3-yl)-N-(methylsulfonyl)-3,6-dihydro-2H-furo[2,3-e]indole-7-carboxamide 
• 1037763-77-1 6-(2,5-difluorobenzyl)-8-(2-methoxypyridin-3-yl)-3,6-dihydro-2H-1-oxa-6-azaasindacene-7-carboxylic acid 
• 1037763-75-9 methyl 6-(2,5-difluorobenzyl)-8-(2-methoxypyridin-3-yl)-3,6-dihydro-2H-furo[2,3-e]indole-7-carboxylate 
• 361393-65-9 1-(2,3-dihydro-1-benzofuran-7-yl)methanamine 
• 123266-63-7 2,3-Dihydro-7-benzofurancarboxylic acid chloride 
• 133844-95-8 2,3-dihydro-benzofuran-7-carboxylic acid methyl ester 
• 108551-60-6 5-bromo-7-carboxy-2,3-dihydrobenzofuran chloride 
• 99517-45-0 methyl benzofuran-7-carboxylate 

Relevant academic research and scientific papers

Discovery and structure-activity relationship of novel 2,3- dihydrobenzofuran-7-carboxamide and 2,3-dihydrobenzofuran-3(2 h)-one-7-carboxamide derivatives as poly(ADP-ribose)polymerase-1 Inhibitors

Novel substituted 2,3-dihydrobenzofuran-7-carboxamide (DHBF-7-carboxamide) and 2,3-dihydrobenzofuran-3(2H)-one-7-carboxamide (DHBF-3-one-7-carboxamide) derivatives were synthesized and evaluated as inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1). A structure-based design strategy resulted in lead compound 3 (DHBF-7-carboxamide; IC50 = 9.45 μM). To facilitate synthetically feasible derivatives, an alternative core was designed, DHBF-3-one-7-carboxamide (36, IC50 = 16.2 μM). The electrophilic 2-position of this scaffold was accessible for extended modifications. Substituted benzylidene derivatives at the 2-position were found to be the most potent, with 3′,4′-dihydroxybenzylidene 58 (IC50 = 0.531 μM) showing a 30-fold improvement in potency. Various heterocycles attached at the 4′-hydroxyl/4′-amino of the benzylidene moiety resulted in significant improvement in inhibition of PARP-1 activity (e.g., compounds 66-68, 70, 72, and 73; IC50 values from 0.718 to 0.079 μM). Compound 66 showed selective cytotoxicity in BRCA2-deficient DT40 cells. Crystal structures of three inhibitors (compounds (-)-13c, 59, and 65) bound to a multidomain PARP-1 structure were obtained, providing insights into further development of these inhibitors.

Synthesis and SAR of highly potent dual 5-HT1A and 5-HT 1B antagonists as potential antidepressant drugs

Novel 5-HT1 autoreceptor ligands based on the N-4-aryl-piperazinyl-N′-ethyl-5,6,7,8-tetrahydropyrido[4′, 3′:4,5]thieno[2,3-d]pyrimidin-4(3H)-one core are described. Aiming at antidepressants with a novel mode of action our objective was to identify potent antagonists showing balanced affinities and high selectivity for the 5-HT 1A and 5-HT1B receptors. Strategies for the development of dual 5-HT1A and 5-HT1B antagonists based on 1 and 2 as leads and the corresponding results are discussed. Isoquinoline analogue 33 displayed high affinity and an antagonistic mode of action for the 5-HT 1A and the 5-HT1B receptors and was characterized further with respect to selectivity, electrically stimulated [3H]5-HT release and in vivo efficacy.

Quaternary ammonium compounds as tachykinin antagonists

The present invention provides a compound of formula (I) wherein R is phenyl, C3-C7cycloalkyl or heteroaryl, each of which being optionally benzo- or C3-C7cycloalkyl-fused and optionally substituted, including in the benzo- or C3-C7cycloalkyl-fused portion, by from 1 to 3 substituents each independently selected from C1-C4alkyl, fluoro(C1-C4)alkyl, C1-C4alkoxy, fluoro(C1-C4)alkoxy, phenoxy, C2-C4alkanoyl, halo, C1-C4alkoxycarbonyl, C3-C7cycloalkyl, —S(O)m(C1-C4alkyl), cyano, —NR2R3, —S(O)mNR2R3, —NR4(C1-C4alkanoyl) and —CONR2R3, or R is 2,3-dihydrobenzo[b]furanyl or chromanyl; R1is H or C1-C6alkyl; W is a direct link, methylene or ethylene; X is unbranched C2-C4alkylene; Y is phenyl, naphthyl, benzyl, pyridyl, thienyl or C3-C7cycloalkyl, each of which being optionally substituted by from 1 to 3 substituents each independently selected from C1-C4alkyl, fluoro(C1-C4)alkyl, C1-C4alkoxy, fluoro(C1-C4)alkoxy, halo and cyano; Ar is phenyl, naphthyl, benzyl, thienyl, benzo[b]thienyl or indolyl, each of which being optionally substituted by from 1 to 3 substituents each independently selected from C1-C4alkyl, fluoro(C1-C4)alkyl, C1-C4alkoxy, fluoro(C1-C4)alkoxy, halo and cyano, or Ar is 1,3-benzodioxolan-4 or 5-yl or 1,4-benzodioxan-5 or 6-yl; ZAis a pharmaceutically acceptable anion; with the proviso that when W is a direct link and R is optionally fused and optionally substituted heteroaryl, said heteroaryl is linked by a ring carbon atom to the carbonyl group. The compounds are tachykinin antagonists.

Synthesis and properties of Biagra [1]. A 5-(2,3-dihydro-7-benzofuryl) analog of Viagra

The synthesis and spectral properties (IR, MS, NMR) of a substituted 5-(2,3-dihydro-7-benzofuryl)pyrazolo[4,3-d]pyrimidin-7-one (2), an analog of Viagra (1), are described. The generally applicable route involves interaction of 2,3-dihydro-7-benzofuranoyl chloride (3) with 4-amino-1-methyl-3-propyl-5-pyrazolecarboxamide (4), and the resulting bis-amide (5) is cyclized to the corresponding substituted pyrazolo[4,3-d]pyrimidin-7-one (6). Chlorosulfonylation of 6, followed by treatment with 1-methylpiperazine, furnished the title compound 2 (named Biagra). Preliminary experiments "associated with the erectile process" on rats lend evidence of greater potency of Biagra (2) as compared to Viagra (1).

Inhibitors of farnesyl-protein transferase

The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras. The compounds of formula A are representative of the compounds of the present invention: STR1

Tetraisoquinoline compounds which have useful pharmaceutical utility

Tetrahydroisoquinoline compounds of formula I STR1 and pharmaceutically acceptable salts and lipophilic ester thereof have utility as analgesics and in the treatment of psychoses, Parinson''s disease, Lesch-Nyan syndrome, attention deficit disorder or cognitive impairment or in the relief of drug dependence or tardive dyskinesia.

Zatosetron, a Potent, Selective, and Long-Acting 5HT3 Receptor Antagonist: Synthesis and Structure-Activity Relationships

Antagonists of 5HT3 receptors are clinically effective in treating nausea and emesis associated with certain oncolytic drugs, including cisplatin.Moreover, these agents may be useful in pharmacological management of several central nervous system disorders, including anxiety, schizophrenia, dementia, and substance abuse.Our studies on aroyltropanamides led to the discovery that dihydrobenzofuranyl esters and amides are potent 5HT3 receptor antagonists.Simple benzoyl derivatives of tropine and 3α-aminotropane possessed weak 5HT3 receptor antagonist activity, as judged by blockade of bradycardia produced by iv injection of serotonin (5HT) to anesthetized rats.Within this series, use of benzofuran-7-carboxamide as the aroyl moiety led to a substantial increase of 5HT3 receptor affinity.The optimal 5HT3 receptor antagonist identified via extensive SAR studies was endo-5-chloro-2,3-dihydro-2,2-dimethyl-N-(8-methyl-8-azabicyclooct-3-yl)-7-benzofurancarboxamide (Z)-2-butenedioate (zatosetron maleate).The 7-carbamyl regiochemistry, dimethyl substitution, chloro substituent, and endo stereochemistry were all crucial elements of the SAR.Zatosetron maleate was a potent antagonist of 5HT-induced bradycardia in rats (ED50=0.86 μg/kg iv).Low oral doses of zatosetron (30 μg/kg) produced long-lasting antagonism of 5HT3 receptors, as evidenced by blockade of 5HT-induced bradycardia for longer than 6 h in rats.Moreover, this compound did not produce hemodynamic effects after iv administration to rats, nor did it block carbamylcholine-induced bradycardia in doses that markedly blocked 5HT3 receptors.Thus, zatosetron is a potent, selective, orally effective 5HT3 receptor antagonist with a long duration of action in rats.

DOPAMINE RECEPTOR LIGANDS AND IMAGING AGENTS

Novel CNS dopamine D-2 receptors, such as the compound 5-iodo-7-N-[(1-ethyl-2-pyrrolidinyl)methyl]carboxamide-2,3-dihydrobenzofura n, are disclosed. These compounds are useful as imaging agents for D-2 receptors in the human brain and exhibit good brain retention and in vivo stability.

Synthesis and characterization of iodobenzamide analogues: Potential D-2 dopamine receptor imaging agents

(S)-N-[(1-Ethyl-2-pyrrolidinyl)methyl]-2-hydroxy-3-iodo-6-methoxybenza mide ([123I]IBZM) is a central nervous system (CNS) D-2 dopamine receptor imaging agent. In order to investigate the versatility of this parent structure in specific dopamine receptor localization and the potential for developing new dopamine receptor imaging agents, a series of new iodinated benzamides with fused ring systems, naphthalene (INAP) and benzofuran (IBF), was synthesized and radiolabeled, and the in vivo and in vitro biological properties were characterized. The best analogue of IBZM is IBF (21). The specific binding of [125I]IBF (21) with rat striatal tissue preparation was found to be saturable and displayed a K(d) of 0.106 ± 0.015 nM. Competition data of various receptor ligands (for [125I]IBF (21) binding show the following rank order of potency: spiperone > IBF (21) > IBZM > (+)-butaclamol > (±)-ADTN,6,7 > ketanserin > SCH-23390 >> propranolol. The in vivo biodistribution results confirm that [125I]IBF (21) concentrated in the striatal area after iv injection into rats. The study demonstrates that [123I]IBF (21) is a potential agent for imaging CNS D-2 dopamine receptors.