61854-89-5

Usage

Chemical Properties

Colorless Viscous Oil

Uses

Protected 3,4-Dihydroxybenzaldehyde (D451000).

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 139-85-5 3,4-dihydroxybenzaldehyde 

Downstream Products

• 130600-77-0 4',3,4-tris(tetrahydropyran-2-yloxy)chalcone 
• 100668-20-0 1-<3,4-bis(tetrahydro-2H-pyran-2-yloxy)phenyl>-1-hexene 
• 121501-50-6 1-<3,4-bis(tetrahydro-2H-pyran-2-yloxy)phenyl>-1-octene 
• 121501-48-2 1-<3,4-bis(tetrahydro-2H-pyran-2-yloxy)phenyl>-1-butene 

Relevant academic research and scientific papers

Synthesis, structure, and antioxidant activity of methoxy- and hydroxyl-substituted 2'-aminochalcones

Abstract: Three 2'-aminochalcone derivatives (E)-1-(2-aminophenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one, (E)-1-(2-aminophenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one, and (E)-1-(2-amino-4,5-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one, have been synthesized, characterized, and tested in vitro in order to assess their antioxidant activity. All compounds were characterized on the basis of 1H NMR, 13C NMR, ESI-mass spectrometry, FT-IR, UV/Vis, and elemental analysis. The X-ray crystal structures of (E)-1-(2-aminophenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one and (E)-1-(2-amino-4,5-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one were successfully determined showing a planar molecule geometry. Studies on the biological properties including test of free radical scavenging ability (DPPH test)?and superoxide dismutase mimetic activity were performed. The results indicate that the aminochalcone carrying two hydroxyl functionalities in adjacent meta and para position exhibits a stronger antioxidant activity than the other derivatives. Graphical abstract: [Figure not available: see fulltext.]

Inhibitory effects of N-(acryloyl)benzamide derivatives on tyrosinase and melanogenesis

Targeting of tyrosinase has proven to be the best means of identifying safe, efficacious, and potent tyrosinase inhibitors for whitening skin. We designed and synthesized ten NAB (N-(acryloyl)benzamide) derivatives (1a–1j) using the Horner-Wadsworth-Emmon

Hydroxy-substituted trans-cinnamoyl derivatives as multifunctional tools in the context of Alzheimer's disease

Alzheimer's disease (AD) is a multifactorial pathology that requires multifaceted agents able to address its peculiar nature. In recent years, a plethora of proteins and biochemical pathways has been proposed as possible targets to counteract neurotoxicity. Although the complex scenario is not completely elucidated, close relationships are emerging among some of these actors. In particular, increasing evidence has shown that aggregation of amyloid beta (Aβ), glycogen synthase kinase 3β (GSK-3β) and oxidative stress are strictly interconnected and their concomitant modulation may have a positive and synergic effect in contrasting AD-related impairments. We designed compound 3 which demonstrated the ability to inhibit both GSK-3β (IC50 = 24.36 ± 0.01 μM) and Aβ42 self-aggregation (IC50 = 9.0 ± 1.4 μM), to chelate copper (II) and to act as exceptionally strong radical scavenger (kinh = 6.8 ± 0.5 · 105 M?1s?1) even in phosphate buffer at pH 7.4 (kinh = 3.2 ± 0.5 · 105 M?1s?1). Importantly, compound 3 showed high-predicted blood-brain barrier permeability, did not exert any significant cytotoxic effects in immature cortical neurons up to 50 μM and showed neuroprotective properties at micromolar concentration against toxic insult induced by glutamate.

Synthesis, characterization, and antioxidant activity of Zn2+ and Cu2+ coordinated polyhydroxychalcone complexes

Four new metal complexes [Cu(ISO)2], [Cu(BUT)2] and [Zn(ISO)2], [Zn(BUT)2] of the polyhydroxychalcones (isoliquiritigenin and butein) are synthesized, structurally characterized and their antioxidant activity is investigated. The formation of the complexes [Cu(ISO)2] and [Zn(ISO)2] is followed by Job’s plot using NMR titration. The resulting compounds are characterized by mass spectrometry, IR spectroscopy, and elemental analysis. Studies on the radical scavenging activity are performed using DPPH as substrate. The results showed that the antioxidant activities of isoliquiritigenin and butein are enhanced after binding to copper or zinc. Graphical abstract: [Figure not available: see fulltext.]

Inhibition of prostaglandin E2 production by synthetic minor prenylated chalcones and flavonoids: Synthesis, biological activity, crystal structure, and in silico evaluation

The discovery of potent inhibitors of prostaglandin E2 (PGE 2) synthesis in recent years has been proven to be an important game changer in pharmaceutical industry. It is known that excessive production of PGE2 triggers a

NOVEL STILBENE ANALOGS

The present invention relates to Stilbene derivatives of the general formula I or a pharmaceutically acceptable salt thereof have properties such as high water solubility, bioavailability and effective as carcinostatics.

Novel Compounds

A compound for use in the treatment of proliferative disorders, such as cancer, having the following formula: wherein: R1, R2 and R3 are independently H or lower alkyl; R4, R5, R6, R7 and R8 are independently H, halo, lower alkyl or —O-lower alkyl, provided that at least one is —O-lower alkyl; or at least one pair of R4 to R8, the members of which pair are adjacent to one another on the ring, are conjoined to form —O—(CR14R15)n—O—, where n is 1 or 2 and R14 and R15 are independently H or lower alkyl, and the remainder of R4 to R8 are independently H, halo, lower alkyl or —O-lower alkyl; and R9, R10, R11, R12 and R13 are independently H, halo, lower alkyl or —O— lower alkyl, provided that at least one is —O-lower alkyl; or at least one pair of R9 to R13, the members of which pair are adjacent to one another on the ring, are conjoined to form —O—(CR16R17)m—O—, where m is 1 or 2 and R16 and R17 are independently H or lower alkyl, and the remainder of R9 to R13 are independently H, halo, lower alkyl or —O-lower alkyl.

4, 6-DIPHENYLPYRID-2-0NES AGAINST CANCER

A compound for use in the treatment of proliferative disorders, such as cancer, having the following formula:z wherein: R1, R2 and R3 are independently H or lower alkyl; R4, R5, R6, R7 and R8 are independently H, halo, lower alkyl or -O-lower alkyl, provided that at least one is -O-lower alkyl; or at least one pair of R4 to R8, the members of which pair are adjacent to one another on the ring, are conjoined to form-0-(CR14R15)n-O-, where n is 1 or 2 and R14 and R15 are independently H or lower alkyl, and the remainder of R4 to R8 are independently H, halo, lower alkyl or -O-lower alkyl; and R9, R10, R11, R12 and R13 are independently H, halo, lower alkyl or -O-lower alkyl, provided that at least one is -O-lower alkyl; or at least one pair of R9 to R13, the members of which pair are adjacent to one another on the ring, are conjoined to form-O-(CR16R17)m-O-, where m is 1 or 2 and R16 and R17 are independently H or lower alkyl, and the remainder of R9 to R13 are independently H, halo, lower alkyl or -O-lower alkyl.

Synthesis and aromatase inhibitory activity of flavanones

Purpose. Aromatase inhibitors are known to prevent the conversion of androgens to estrogens and play a significant role in the treatment of estrogen dependent diseases such as breast cancer. Some flavonoids have been reported as potent aromatase inhibitors; therefore, in an effort to develop novel anti breast cancer agents, B ring substituted flavanones with a 7-methoxy group on A ring were synthesized and tested to assess their ability to inhibit aromatase activity and to determine the optimal B ring substitution pattern. Methods. A series of flavanones was prepared by cyclisation of 2′hydroxychalcones previously obtained by Claisen-Schmidt condensation and the aromatase inhibitory activity of these compounds was investigated using human placental microsomes and radiolabeled [1,2,6,7-3H]-androstenedione as substrate. Results. Almost all flavanones exhibited inhibitory effect on the aromatase activity but their potency was dependent on their B ring substitution pattern. Hydroxylation at position 3′ and/or 4′ enhanced the anti-aromatase activity; thus, 3′,4′-dihydroxy-7-methoxyflavanone was found to be twice more potent than aminoglutethimide, the first aromatase inhibitor clinically used. Conclusions. These results indicated that these flavanones could be considered as potential anti breast cancer agents through the inhibition of aromatase activity and allowed us to select some of these compounds as skeleton for the development of flavonoid structurally-related aromatase inhibitors.

Synthesis and anti-inflammatory effect of chalcones

The process of degranulation of mast cells and neutrophils contributes to inflammatory disorders. Activation of microglial cells and macrophages is believed to be involved in inflammatory, infectious and degenerative diseases of the CNS. Combining the pot