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Usage

Uses

Used in Pharmaceutical Industry:
2-METHYLFURAN-3-CARBONYL CHLORIDE is used as an intermediate in the synthesis of pharmaceuticals for its ability to undergo various chemical reactions, including acylation and nucleophilic substitution. Its reactivity allows for the creation of new compounds with potential therapeutic properties.
Used in Agrochemical Industry:
2-METHYLFURAN-3-CARBONYL CHLORIDE is also used as an intermediate in the synthesis of agrochemicals, where its reactive nature enables the development of new compounds for agricultural applications, such as pesticides and herbicides, to improve crop protection and yield.

InChI:InChI=1/C6H5ClO2/c1-4-5(6(7)8)2-3-9-4/h2-3H,1H3

Upstream product

• 6947-94-0 2-methyl-3-furancarboxylic acid 
• 97-97-2 chloroacetaldehyde dimethyl acetal 
• 141-97-9 ethyl acetoacetate 
• 3416-93-1 2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline 
• 79-37-8 oxalyl dichloride 
• 6141-58-8 methyl 2-methyl-3-furancarboxylate 
• 28921-35-9 2-methyl-3-ethoxycarbonyl-furan 

Downstream Products

• 881309-37-1 methyl (Z)-{4,4-difluoro-1-[4-(5-methyloxazole-4-carbonylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepin-5-ylidene}acetate 
• 1570135-57-7 N-(2-(4,5-dihydrooxazol-2-yl)phenyl)-2-methylfuran-3-carboxamide 
• 1369525-63-2 N-(2-hydroxybenzoyl)-2-methylfuran-3-carboxamide 
• 75596-44-0 2-methylfuran-3-carboxylic acid benzylamide 
• 1330033-95-8 2-methyl-5-pyridin-3-ylfuran-3-carboxylic acid benzylamide 

Relevant academic research and scientific papers

Design, synthesis and antifungal activity of novel fenfuram-diarylamine hybrids

Ten novel fenfuram-diarylamine hybrids were designed and synthesized. And their antifungal activities against four phytopathogenic fungi have been evaluated in vitro and most of the compounds demonstrated a significant antifungal activities against Rhizoctonia solani and Sclerotinia sclerotiorum. Compound 5e exhibited the most potent antifungal activity against R. solani with an EC50value of 0.037 mg/L, far superior to the commercially available fungicide boscalid (EC50= 1.71 mg/L) and lead fungicide fenfuram (EC50= 6.18 mg/L). Furthermore, scanning electron microscopy images showed that the mycelia on treated media grew abnormally with tenuous, wizened and overlapping colonies compared to the negative control. Molecular docking studies revealed that compound 5e featured a higher affinity for succinate dehydrogenase (SDH) than fenfuram. Furthermore, it was shown that the 3-chlorophenyl group in compound 5e formed a CH-π interaction with B/Trp-206 and a Cl-π interaction with D/Tyr-128, rendering compound 5e more active than fenfuram against SDH.

Discovery of potent inhibitors of Schistosoma mansoni NAD+ catabolizing enzyme

The blood fluke Schistosoma mansoni is the causative agent of the intestinal form of schistosomiasis (or bilharzia). Emergence of Schistosoma mansoni with reduced sensitivity to praziquantel, the drug currently used to treat this neglected disease, has underlined the need for development of new strategies to control schistosomiasis. Our ability to screen drug libraries for antischistosomal compounds has been hampered by the lack of validated S. mansoni targets. In the present work, we describe a virtual screening approach to identify inhibitors of S. mansoni NAD+ catabolizing enzyme (SmNACE), a receptor enzyme suspected to be involved in immune evasion by the parasite at the adult stage. Docking of commercial libraries into a homology model of the enzyme has led to the discovery of two in vitro micromolar inhibitors. Further structure-activity relationship studies have allowed a 3-log gain in potency, accompanied by a largely enhanced selectivity for the parasitic enzyme over the human homologue CD38.

Cu(II)-mediated C-H amidation and amination of arenes: Exceptional compatibility with heterocycles

A Cu(OAc)2-mediated C-H amidation and amination of arenes and heteroarenes has been developed using a readily removable directing group. A wide range of sulfonamides, amides, and anilines function as amine donors in this reaction. Heterocycles present in both reactants are tolerated, making this a broadly applicable method for the synthesis of a family of inhibitors including 2-benzamidobenzoic acids and N-phenylaminobenzoates.

Complementary regioselectivity in Rh(III)-catalyzed insertions of potassium vinyltrifluoroborate via C-H activation: Preparation and use of 4-trifluoroboratotetrahydroisoquinolones

Potassium vinyltrifluoroborate was found to be an efficient partner with benzamide derivatives for Rh(III)-catalyzed annulations. 4- Trifluoroboratotetrahydroisoquinolones were generated under mild conditions, affording a regioisomerically complementary substitution pattern to other alkenes in related reactions. These new boron-containing building blocks were derivatized by N-arylations, retaining the boron substituent for further elaboration.

Pyrazolo[3,4-b]pyridine compounds, and their use as a PDE4 inhibitors

The invention provides a compound of formula (I) or a salt thereof: wherein R2 is H, C1-3alkyl, n-butyl, C1-2fluoroalkyl, cyclopropyl, cyclobutyl, (cyclopropyl)methyl-, —CN, or —CH2OH; R3 is inter alia optionally substituted C4-7cycloalkyl or an optionally substituted heterocyclic group (aa), (bb) or (cc); Ra is H, methyl or ethyl; Rb is H or methyl; R4 is H, methyl, ethyl, n-propyl, —C(O)-Me, or —C(O)—C1fluoroalkyl; and R5 is: —C(O)—(CH2)n—Ar, —C(O)-Het, —C(O)—C1-6alkyl, —C(O)—C1 fluoroalkyl, —C(O)—(CH2)2—C(O)—NR15bNR15b, —C(O)—CH2—C(O)—NR15bNR15b, —C(O)—NR15b—(CH2)m1—Ar, —C(O)—NR15b—Het, —C(O)—NR15b—C1-6alkyl, —C(O)—NR5aR5b, —S(O)2—(CH2)m2—Ar, —S(O)2-Het, —S(O)2—C1-6alkyl, or —CH2—Ar; or R4 and R5 taken together are —(CH2)p1—, —(CH2)2—X5—(CH2)2—, —C(O)—(CH2)p2—, —C(O)—N(R15)—(CH2)p3—; or NR4R5 is of sub-formula (y), (y1), (y2) or (y3). The invention provides the use of the compounds as inhibitors of phosphodiesterase type IV (PDE4) and/or for the treatment and/or prophylaxis of inflammatory and/or allergic diseases such as COPD and the like.

PYRAZOLO[3,4-B]PYRIDINE COMPOUNDS, AND THEIR USE AS PDE4 INHIBITORS

The invention provides a compound of formula (I) or a salt thereof: wherein R2 is H, C1-3alkyl, n butyl, C1-2fluoroalkyl, cyclopropyl, cyclobutyl, (cyclopropyl)methyl , CN, or CH2OH; R3 is inter alia optionally substituted C4-7cycloalkyl or an optionally substituted heterocyclic group (aa), (bb) or (cc); Ra is H, methyl or ethyl; Rb is H or methyl; R4 is H, methyl, ethyl, n propyl, C(O) Me, or C(O) C1fluoroalkyl; and R5 is: C(O) (CH2)n Ar, C(O) Het, C(O) C1 6alkyl, C(O) C1fluoroalkyl, C(O) (CH2)2 C(O) NR15bNR15b, C(O) CH2 C(O) NR15bNR15b, C(O) NR15b (CH2)m1 Ar, C(O) NR15b Het, C(O) NR15b C1-6 alkyl, C(O) NR5aR5b, S(O)2 (CH2)m2-Ar, S(O)2 Het, S(O)2-C1-6alkyl, or CH2 Ar; or R4 and R5 taken together are-(CH2)p1-, (CH2)2 X5 (CH2)2 , C(O) (CH2)p2 ,-C(O)-N(R15) (CH2)p3 ; or NR4R5 is of sub-formula (y), (y1), (y2) or (y3). The invention also provides the use of the compounds as inhibitors of phosphodiesterase type IV (PDE4) and/or for the treatment and/or prophylaxis of inflammatory and/or allergic diseases such as chronic obstructive pulmonary disease (COPD), asthma, rheumatoid arthritis, allergic rhinitis, psoriasis or atopic dermatitis.

Synthesis and biological activity of novel 4,4-difluorobenzazepine derivatives as non-peptide antagonists of the arginine vasopressin V 1A receptor

To find potent and selective antagonists of the arginine vasopressin (AVP) V1A receptor, optimization studies of compounds structurally related to (Z)-N-{4′-[(4,4-difluoro-5-carbamoylmethylidene-2,3,4,5-tetrahydro-1H- 1-benzazepin-1-yl)carbonyl

USE OF THIOCARBOXANILIDE DERIVATIVES FOR THE PREPARATION OF A MEDICAMENT FOR PREVENTING THE TRANSMISSION OF HIV TO UNINFECTED CELLS AND CONTRACEPTIVE COMPOSITIONS COMPRISING THE SAID DERIVATIVES

Method for preventing or inhibiting the transmission of HIV to susceptible uninfected cells by administering to the HIV, to cells infected with HIV, and/or to the uninfected cells, an effective amount of a compound of formula (I), wherein X is O or S, prior to the HIV or the cells infected with HIV, contacting the uninfected cells.