480-97-7

Basic information

• Product Name: Karanjol
• Synonyms: 4-Hydroxybenzofuran;Karanjol;Benzofuran-4-ol;1-Benzofuran-4-ol;4-Benzofuranol
• CAS NO: 480-97-7
• Molecular Formula: C₈H₆O₂
• Molecular Weight: 134.13204
• Mol File: 480-97-7.mol

Chemical Properties

• Melting Point: 56-58℃
• Boiling Point: 108℃
• Flash Point: 19℃
• Appearance: /
• Density: 1.280
• PKA: 9.04±0.40(Predicted)
• CAS DataBase Reference: Karanjol(CAS DataBase Reference)
• NIST Chemistry Reference: Karanjol(480-97-7)
• EPA Substance Registry System: Karanjol(480-97-7)

Safety Data

• Hazardous Substances Data: 480-97-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Karanjol is used as a pharmaceutical compound for its anti-inflammatory, antifungal, and insecticidal properties. It has been found to be effective in treating various skin conditions and fungal infections, as well as in controlling pests in agriculture.
Used in Cosmetic Industry:
In the cosmetic industry, Karanjol is used as an ingredient in skincare products for its anti-inflammatory and antimicrobial properties. It helps in reducing skin inflammation and promoting a healthy skin barrier.
Used in Agrochemical Industry:
Karanjol is used as an active ingredient in agrochemicals for its insecticidal properties. It is employed in the development of biopesticides to control pests in agriculture, providing an eco-friendly alternative to synthetic chemicals.
Used in Research and Development:
Karanjol is used as a research chemical for the synthesis of various derivatives, such as 4and 5-hydroxybenzofurans and their amino derivatives. These compounds have potential applications in the development of new drugs and pharmaceuticals.

Upstream product

• 98-01-1 furfural 
• 108-24-7 acetic anhydride 
• 150-90-3 sodium succinate 
• 487-56-9 karanjic acid 
• 860540-64-3 (2-formyl-3-hydroxy-phenoxy)-acetic acid 
• 127-09-3 sodium acetate 
• 16806-93-2 4-oxo-4,5,6,7-tetrahydrobenzofuran 
• 112678-09-8 3-carboxy-4-hydroxybenzo-(b)-furan 
• 19278-81-0 4-hydroxy-1-benzofuran-3(2H)-one 
• 113511-42-5 4-hydroxybenzofuran-2-carboxylic acid 
• 699-83-2 2,6-dihydroxylacetophenone 

Downstream Products

• 18014-96-5 4-methoxybenzofuran 
• 144822-82-2 4-hydroxy-2,3-dihydrobenzofuran 
• 59292-71-6 4-hydroxybenzofuran-5-carboxaldehyde 
• 688781-79-5 4-(2-fluoro-4-nitrophenoxy)-1-benzofuran 
• 475481-76-6 4-benzyloxy-benzofuran 
• 1033810-77-3 4-(2-chloro-4-nitrophenoxy)-1-benzofuran 
• 1361944-51-5 4-phenyl-2H-furo[2,3-h]-1-benzopyran-2-one 
• 6457-92-7 4-methyl-2H-furo[2,3-h]-1-benzopyran-2-one 
• 1361944-41-3 4-benzofuranyl phenylpropiolate 
• 64663-60-1 4-hydroxy-2-phenylbenzofuran 
• 177734-79-1 benzofuran-4-yl trifluoromethanesulfonate 
• 95333-15-6 4-acetylbenzofuran 
• 412336-07-3 4-aminobenzofuran 
• 475481-77-7 4-benzyloxy-benzofuran-7-carbaldehyde 

Relevant articles and documents

COMPOUNDS AND METHODS FOR TREATING HIV INFECTIONS

The present invention is directed to novel nanomolar and picomolar inhibitors of HIV reverse transcriptase, pharmaceutical compositions therefrom and methods for inhibiting reverse transcriptase and treating HIV infections, especially included drug resistant strains of HIV-1 and HIV-2 and/or secondary disease states and/or conditions which occur as a consequence of HIV infection.

NOVEL TRICYCLIC CALCIUM SENSING RECEPTOR ANTAGONISTS

Novel tricyclic compounds of Formula (I) and pharmaceutically acceptable salts thereof are disclosed as useful for treating or preventing osteoporosis and similar conditions. The compounds are effective as calcium sensing receptor antagonists. Pharmaceutical compositions and methods of treatment are also included.

NOVEL TRICYCLIC CALCIUM SENSING RECEPTOR ANTAGONISTS FOR THE TREATMENT OF OSTEOPOROSIS

Novel tricyclic compounds of the formula (I): and pharmaceutically acceptable salts thereof are disclosed as useful for treating or preventing osteoporosis and similar conditions. The compounds are effective as calcium sensing receptor antagonists. Pharmaceutical compositions and methods of treatment are also included.

Synthetic models related to methoxalen and menthofuran-cytochrome P450 (CYP) 2A6 interactions. Benzofuran and coumarin derivatives as potent and selective inhibitors of CYP2A6

Human microsomal cytochrome P450 (CYP) 2A6 contributes extensively to nicotine detoxication but also activates tobacco-specific procarcinogens to mutagenic products. We prepared a series of benzofuran and coumarin derivatives that have inhibitory effects on the activity of human CYP2A6. The reported compounds methoxalen and menthofuran had potent inhibitory effects on the activity of CYP2A6 with IC50 values of 0.47 μM and 1.27 μM, respectively. Synthetic benzofuran (4-methoxybenzofuran: IC50=2.20 μM) and coumarin (5-methoxycoumarin: IC50=0.13 μM and 6-methoxycoumarin: IC50=0.64 μM) derivatives, which have more selective effects than those of methoxalen and menthofuran, exhibited comparable activities against CYP2A6. These compounds can be used as a lead compounds in the design of CYP2A6 inhibitor drugs to reduce smoking and tobacco-related cancers.

Picomolar inhibitors of HIV reverse transcriptase featuring bicyclic replacement of a cyanovinylphenyl group

Members of the catechol diether class are highly potent non-nucleoside inhibitors of HIV-1 reverse transcriptase (NNRTIs). The most active compounds yield EC50 values below 0.5 nM in assays using human T-cells infected by wild-type HIV-1. However, these compounds such as rilpivirine, the most recently FDA-approved NNRTI, bear a cyanovinylphenyl (CVP) group. This is an uncommon substructure in drugs that gives reactivity concerns. In the present work, computer simulations were used to design bicyclic replacements for the CVP group. The predicted viability of a 2-cyanoindolizinyl alternative was confirmed experimentally and provided compounds with 0.4 nM activity against the wild-type virus. The compounds also performed well with EC50 values of 10 nM against the challenging HIV-1 variant that contains the Lys103Asn/Tyr181Cys double mutation in the RT enzyme. Indolyl and benzofuranyl analogues were also investigated; the most potent compounds in these cases have EC50 values toward wild-type HIV-1 near 10 nM and high-nanomolar activities toward the double-variant. The structural expectations from the modeling were much enhanced by obtaining an X-ray crystal structure at 2.88 A resolution for the complex of the parent 2-cyanoindolizine 10b and HIV-1 RT. The aqueous solubilities of the most potent indolizine analogues were also measured to be ～40 μg/mL, which is similar to that for the approved drug efavirenz and ～1000-fold greater than for rilpivirine.

Palladium-catalyzed intramolecular hydroarylation of 4-benzofuranyl alkynoates. Approach to angelicin derivatives

Intramolecular hydroarylation of 4-benzofuranyl alkynoates using Pd(OAc)2 as catalyst took place selectively and efficiently, giving angular furocoumarin derivatives in high yields. The parent angelicin was obtained in 80% yield by this method.

4-Phenoxybutoxy-substituted heterocycles - A structure-activity relationship study of blockers of the lymphocyte potassium channel Kv1.3

The voltage-gated potassium channel Kv1.3 constitutes an attractive pharmacological target for the treatment of effector memory T cell-mediated autoimmune diseases such as multiple sclerosis and psoriasis. Using 5-methoxypsoralen (5-MOP, 1), a compound isolated from Ruta graveolens, as a template we previously synthesized 5-(4-phenoxybutoxy)psoralen (PAP-1, 2) which inhibits Kv1.3 with an IC50 of 2 nM. Since PAP-1 is more than 1000-fold more potent than 5-MOP, we here investigated whether attaching a 4-phenoxybutoxy side chain to other heterocyclic systems would also produce potent Kv1.3 blockers. While 4-phenoxybutoxy-substituted quinolines, quinazolines and phenanthrenes were inactive, 4-phenoxybutoxy-substituted quinolinones, furoquinolines, coumarins or furochromones inhibited Kv1.3 with IC50s of 150 nM to 10 μM in whole-cell patch-clamp experiments. Our most potent new compound is 4-(4-phenoxybutoxy)-7H-furo[3,2-g]chromene-7-thione (73, IC50 17 nM), in which the carbonyl oxygen of PAP-1 is replaced by sulfur. Taken together, our results demonstrate that the psoralen system is a crucial part of the pharmacophore of phenoxyalkoxypsoralen-type Kv1.3 blockers.

Anti-cancer agents and uses thereof

The present invention is in the area of novel compounds and salts thereof, their syntheses, and their use as anti-cancer agents. The compounds include compounds of Formula I: and solvates, hydrates and pharmaceutically-acceptable salts thereof, wherein A1 is N or CR1; A3 is N or CR3; A5 is N or CR5; R1, R3-R6 and L are defined in the specification; n is 0 or 1; and X is an optionally-substituted aryl group having 6-10 carbons in the ring portion, an optionally-substituted 6-membered heteroaryl group having 1-3 nitrogen atoms in the ring portion, an optionally-substituted 5-membered heteroaryl group having 0-4 nitrogen atoms in the ring portion and optionally having 1 sulfur atom or 1 oxygen atom in the ring portion, or an optionally-substituted heteroaryl group in which a 6-membered ring is fused either to a 5-membered ring or to a 6-membered ring, wherein in each case 1, 2, 3 or 4 ring atoms are heteroatoms independently selected from nitrogen, oxygen and sulfur. They are effective against a broad range of cancers, especially leukemia, prostate, non-small cell lung and colon. They are additionally useful in the treatment of proliferative retinopathies such as diabetic neuropathy and macular degeneration.

9-AZABICYCLO [3 . 3 . 1] NONANE DERIVATIVES AS MONOAMINE REUPTAKE INHIBITORS

The present invention relates to a 9-azabicyclo[3.3.1]nonane derivative of formula (I), wherein R1 is H or C1-5alkyl; X is O or NR2, wherein R2 is H, C1-5alkyl or C2-5acyl and Ar is C6-10aryl or a 5-10 membered heteroaryl ring system, both being optionally substituted with one to three of R3-R5 independently selected from halogen, C1-5alkyl, C1-5alkoxy, C3-6cycloalkyl, C2-5alkenyl, C2-5alkynyl, CN, NO2, hydroxy, phenyl, phenoxy and phenylC1-2alkoxy, wherein said C1-5alkyl and C1-5alkoxy are optionally substituted with one to three halogens and wherein said phenyl, phenoxy and phenylC1-2alkoxy are optionally substituted with one to three substituents independently selected from halogen and methyl or two of R3-R5 at adjacent positions together form a methylenedioxy or propylene unit, with the proviso that the compounds exo-9-methyl-3-phenoxy-9-azabicyclo[3.3.1]nonane and N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-1H indazole-5-amine are excluded, or a pharmaceutically acceptable salt or solvate thereof. The invention also relates to pharmaceutical compositions comprising said 9-azabicyclo[3.3.1]nonane derivatives and to their use in therapy.

Facile entry to 4- and 5-hydroxybenzofuran and to their amino derivatives

An innovative one-step procedure for the synthesis of 4-hydroxybenzofuran and an improved synthesis of 5-hydroxybenzofuran is reported. Such compounds were also transformed into their amino derivatives via Smiles rearrangement with good to high overall yields. Copyright Taylor & Francis Group, LLC.