5594-97-8

Usage

Uses

Used in Pharmaceutical Industry:
2-hydroxy-4H-benzo[h]chromen-4-one is used as a precursor in the synthesis of pharmaceuticals for its potential therapeutic applications in treating various diseases and conditions. Its antioxidant, anti-inflammatory, and anti-cancer properties make it a valuable compound in the development of new drugs.
Used in Agrochemical Industry:
2-hydroxy-4H-benzo[h]chromen-4-one is used as a precursor in the synthesis of agrochemicals, contributing to the development of effective and environmentally friendly products for agriculture.
Used in Organic Synthesis:
2-hydroxy-4H-benzo[h]chromen-4-one is used as a key intermediate in organic synthesis, allowing for the creation of a variety of biologically active molecules and complex organic compounds.
Used in Drug Development:
2-hydroxy-4H-benzo[h]chromen-4-one is used in the development of pharmaceutical drugs, leveraging its antioxidant, anti-inflammatory, and anti-cancer properties to create novel therapeutic agents for the treatment of various diseases and conditions.

Upstream product

• 141-82-2 malonic acid 
• 90-15-3 α-naphthol 
• 7446-70-0 aluminium trichloride 
• 711-79-5 1-hydroxy-2-acetonaphthone 
• 105-58-8 Diethyl carbonate 
• 574-19-6 1-(2-hydroxy-1-naphthyl)ethan-1-one 
• 60179-48-8 Malonsaeure-mono-α-naphthylester 
• 830-81-9 1-naphthyl acetate 
• 211449-32-0 Diethyl-carbamic acid 2-acetyl-naphthalen-1-yl ester 
• 876512-92-4 1-(1-ethoxycarbonyloxy-[2]naphthyl)-ethanone 
• 108-88-3 toluene 
• 211449-42-2 N,N-Diethyl-3-(1-hydroxy-naphthalen-2-yl)-3-oxo-propionamide 

Downstream Products

• 1594-37-2 3-[4-(3-methyl-4-phenyl-3H-thiazol-2-ylidene)-but-2-enylidene]-benzo[h]chromene-2,4-dione 
• 1661-70-7 3-[2-(3-methyl-4-phenyl-3H-thiazol-2-ylidene)-ethylidene]-benzo[h]chromene-2,4-dione 
• 1449795-53-2 C₂₇H₁₇NO₂ 
• 1537195-86-0 6-amino-5-((4-hydroxy-2-oxo-2H benzo[h]chromen 3-yl)(4-(trifluoromethyl)phenyl)methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 
• 1537195-85-9 6-amino-5-((3,4-dimethoxyphenyl)(4-hydroxy-2-oxo-2H-benzo[h]chromen-3-yl)methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 
• 1638691-53-8 3-amino-1-(2-nitrophenyl)-12-oxo-1,12-dihydrobenzo[h]pyrano[3,2-c]chromene-2-carbonitrile 
• 1638691-55-0 3-amino-1-(4-nitrophenyl)-12-oxo-1,12-dihydrobenzo[h]pyrano[3,2-c]chromene-2-carbonitrile 
• 1638691-57-2 3-amino-1-(2-methoxyphenyl)-12-oxo-1,12-dihydrobenzo[h]pyrano[3,2-c]chromene-2 carbonitrile 
• 1638691-59-4 3-amino-1-(4-methoxyphenyl)-12-oxo-1,12-dihydrobenzo[h]pyrano[3,2-c]chromene-2 carbonitrile 
• 1638691-61-8 3-amino-12-oxo-1-(3,4,5-trimethoxyphenyl)-1,12-dihydrobenzo[h]pyrano[3,2-c]chromene-2-carbonitrile 
• 1638691-63-0 3-amino-1-(2-chlorophenyl)-12-oxo-1,12-dihydrobenzo[h]pyrano[3,2-c]chromene-2-carbonitrile 
• 1579230-60-6 2-(naphtho[2,1-d]isoxazole-3-yl)-N-p-tolylacetamide 
• 1579230-62-8 2-(naphtho[2,1-d]isoxazole-3-yl)-N-phenylacetamide 
• 1579230-65-1 N-(4-bromophenyl)-2-(naphtho[2,1-d]isoxazole-3-yl)acetamide 

Relevant academic research and scientific papers

Synthesis, biological evaluation and molecular docking of 4-Amino-2H-benzo[h]chromen-2-one (ABO) analogs containing the piperazine moiety

Prostate cancer (PCa) is a major cause of cancer-related male death in worldwide. To develop of potential anti-prostate cancer agents, 22 kinds of 4-Amino-2H-benzo[h]chromen-2-one analogs were designed and synthesized as potent androgen receptor (AR) anta

Antitumor agents. 254. Synthesis and biological evaluation of novel neo-tanshinlactone analogues as potent anti-breast cancer agents

In our previous study, neo-tanshinlactone (1) showed potent and selective anti-breast cancer activity. To explore the SAR of 1, nine analogues (15-18, 24-28) were designed and synthesized. Together with 1 and tamoxifen (TAM), all newly synthesized compounds and some intermediates were evaluated for in vitro anticancer activity against several human tumor cell lines. Compounds without a ring D did not show promising activity, while compounds with a methylated furan ring D showed better activity than those with unsubstituted furan or hydroxy-dihydrofuran rings. Among all newly synthesized compounds, compound 15 with an ethyl group at the 4-position showed the best activity and selectivity with ED50 values of 0.45 and 0.18 μg/mL against MCF-7 and ZR-75-1 (ER+) and 13.5 and 10.0 μg/mL against MDA MB-231 and HS 587-1 (ER-), respectively. Furthermore, 15 also showed potent activity against SK-BR-3 (ER-, HER2+) with an ED50 value of 0.10 μg/mL. Our preliminary SAR studies showed that a methylated furan ring D and the C-4 substituent in ring A are critical for anti-breast cancer activity. Further development of 1 and 15 as anti-breast cancer drug candidates is warranted.

Molecular hybridization used to design and synthesize neo-tanshinlactone derivatives as PD-1/PD-L1 inhibitors

Four series of molecular hybrids (37 final products) of neo-tanshinlactone, a natural product extracted from Salvia miltiorrhiza Bunge, and known PD-1/PD-L1 interaction inhibitors were prepared as possible chemotherapeutic agents against triple negative breast cancer. Screening using a homogenous time-resolved fluorescence method resulted in three lead compounds (MZ52 IC50 74 ± 4 nM; MZ58 IC50 134 ± 17 nM; MZ61 IC50 225 ± 19 nM). With less T cell cytotoxicity and effects in activating CD8+ T cells in a T cell proliferation assay and a functionality experiment, MZ58 was selected as the best candidate for animal experiments. MZ58 exhibited antitumor effects in a subcutaneous transplantation tumor model as well as effects in reducing T cell exhaustion. In conclusion, after in vivo and in vitro experiments, we successfully acquired an effective candidate (MZ58) showing antitumor effects with low cytotoxicity toward T cells as well as the ability to activate CD8+ T cells and reduce T cell exhaustion.

Chromenone derivatives as a versatile scaffold with dual mode of inhibition of HIV-1 reverse transcriptase-associated Ribonuclease H function and integrase activity

A number of compounds targeting different processes of the Human Immunodeficiency Virus type 1 (HIV-1) life cycle have been developed in the continuing fight against AIDS. Coumarin-based molecules already proved to act as HIV-1 Protease (PR) or Integrase (IN) inhibitors and also to target HIV-1 reverse transcriptase (RT), blocking the DNA-dependent DNA-polymerase activity or the RNA-dependent DNA-polymerase activity working as common NNRTIs. In the present study, with the aim to exploit a coumarin-based scaffold to achieve the inhibition of multiple viral coded enzymatic functions, novel 4-hydroxy-2H, 5H-pyrano (3, 2-c) chromene–2, 5–dione derivatives were synthesized. The modeling studies calculated the theoretical binding affinity of the synthesized compounds on both HIV-1 IN and RT-associated Ribonuclease H (RNase H) active sites, which was confirmed by biological assays. Our results provide a basis for the identification of dual HIV-1 IN and RT RNase H inhibitors compounds.

Regioselective Synthesis of 4,5-Dihydro-6H-oxepino[3,2-c]chromene-2,6(3H)-diones through Palladium-Catalyzed Intramolecular Alkoxycarbonylation of 3-Allyl-4-hydroxycoumarins

Seven-membered ring lactones fused to coumarin scaffolds were obtained via a palladium-catalyzed regioselective intramolecular alkoxycarbonylation under a CO atmosphere. Cyclocarbonylation of 3-allyl-4-hydroxycoumarin derivatives was accessed in the absen

ATF3 INDUCTION COMPOUNDS

Provided are compounds for treating and/or preventing obesity and obesity-related disorders. Particularly, provided are chromanone derivatives used as ATF3 inducer and for treating and/or preventing obesity and obesity-related disorders such as heart disease, hypertension, hyperlipidemia and diabetes.

One-pot two-step synthesis of 3-iodo-4-aryloxy coumarins and their Pd/C-catalyzed annulation to coumestans

An efficient protocol for the synthesis of various coumestans from the intramolecular annulation of 3-iodo-4-aryloxy coumarins through C-H activation has been developed. When 3-iodo-4-aryloxy coumarins were treated with 10% Pd/C (0.3 mol% Pd) in the presence of sodium acetate, the corresponding coumestans were produced in good to excellent yield. Reusability of the palladium catalyst was investigated in up to three consecutive cycles and it was found that the yield of the reaction was almost unaltered. Sequential iodination and O-arylation of 4-hydroxy coumarins leading to the 3-iodo-4-aryloxy coumarins were also achieved in a one-pot two-step process starting from aryl iodides in high yield. Pivalic acid was revealed to be the most effective additive for the later method to produce 3-iodo-4-phenoxy coumarins. Different functional groups bearing electron-donating as well as withdrawing groups are also tolerant to the reaction conditions.

Benzocoumarin compound having anti-breast cancer activity and preparation method thereof

The invention discloses a benzocoumarin compound having an anti-breast cancer activity and a preparation method of the benzocoumarin compound, and belongs to the technical field of pharmaceutical chemistry. The key points of the technical scheme are as follows: the benzocoumarin compound having the anti-breast cancer activity is a 4-chlorine-[7,8]benzocoumarin-3-aldehyde, and the structural formula is shown in the description. The invention further specifically discloses the preparation method of the benzocoumarin compound having the anti-breast cancer activity. MTT experiments show that the synthesized compound has an excellent in-vitro anti-breast cancer cell proliferation activity, remarkably inhibits the growth of human breast cancer cells MCF-7, MDA-MB-231, and can be further developed as an antineoplastic drug or a lead compound.

Synthesis and cytotoxic activity of some novel dihyrobenzo[h]pyrano [3,2-c]chromene derivatives

Three-component reaction of 4-hydroxy-2H-benzo[h]chromen-2-one, aromatic aldehydes, and malononitrile in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) in ethanol at room temperature affords good yields of novel dihyrobenzo[h]pyrano[3,2-c]chromene

Synthesis of new naphthoisoxazole amide derivatives and study of their biological evaluations

A series of naphthoisoxazole amide derivatives 4a-h have been synthesized from naphthoisoxazole acetic acid 3. 2-Acetyl-1-naphthol-1 on reaction with pulverized sodium and diethyl carbonate gave 4-hydroxy naphthopyrone 2 which on Posner reaction gave naphthoisoxazole acetic acid 3. The cytotoxic activity study for inhibiting melanoma cell survival was evaluated on a series of melanoma cell lines. The anticonvulsant activity of these compounds has been evaluated in Wistar rats. A compound called 4h has been found to have anticonvulsant activity comparable to that of the standard drug phenytoin. Springer Science+Business Media 2014.