76240-26-1

Upstream product

• 61080-20-4 2-(chloromercurio)-4,5-(methylenedioxy)phenol 
• 76240-25-0 7-benzyloxy-2H-1-benzopyran 
• 70371-58-3 1-(benzyloxy)-3-(prop-2-yn-1-yloxy)benzene 
• 108-46-3 recorcinol 
• 76240-24-9 7-benzyloxy-3,4-dihydro-2H-1-benzopyran-4-ol 
• 6941-70-4 2-bromo-4,5-methylenedioxyphenol 
• 533-31-3 Sesamol 
• 76240-23-8 3-(3-Hydroxyphenoxy)propanenitrile 
• 76240-27-2 7-hydroxy-2,3-dihydro-4H-chromen-4-one 
• 31042-20-3 7-(benzyloxy)chroman-4-one 
• 144852-07-3 3-(3-benzyloxyphenoxy)propionaldehyde dimethyl acetal 
• 3769-41-3 3-Benzyloxyphenol 

Downstream Products

• 19839-21-5 3-Benzyloxy-5,8,10,12-tetraoxa-benzo[a]cyclopenta[h]fluoren-6-one 
• 65418-33-9 (+/-)-neorautenane 
• 1983-72-8 medicagol 
• 84297-59-6 rac-cabenegrin A-I 
• 245678-56-2 (-)-3[1-S-N(1-methyl)benzylcarbamoyl]-6aR,11aR-maackiain 
• 245678-49-3 (+)-3[1-S-N(1-methyl)benzyl-carbamoyl]-6aS,11aS-maackiain 
• 2035-15-6 (+/-)-3-hydroxy-8,9-methylenedioxyprerocarpan 

Relevant academic research and scientific papers

Maackiain is a novel antiallergic compound that suppresses transcriptional upregulation of the histamine H1 receptor and interleukin-4 genes

Kujin contains antiallergic compounds that inhibit upregulation of histamine H1 receptor (H1R) and interleukin (IL)-4 gene expression. However, the underlying mechanism remains unknown. We sought to identify a Kujin-derived antiallergic compound and investigate its mechanism of action. The H1R and IL-4 mRNA levels were determined by real-time quantitative RT-PCR. To investigate the effects of maackiain in?vivo, toluene-2,4-diisocyanate (TDI)-sensitized rats were used as a nasal hypersensitivity animal model. We identified (?)-maackiain as the responsible component. Synthetic maackiain showed stereoselectivity for the suppression of IL-4 gene expression but not for H1R gene expression, suggesting distinct target proteins for transcriptional signaling. (?)-Maackiain inhibited of PKCδ translocation to the Golgi and phosphorylation of Tyr311 on PKCδ, which led to the suppression of H1R gene transcription. However, (?)-maackiain did not show any antioxidant activity or inhibition of PKCδ enzymatic activity per se. Pretreatment with maackiain alleviated nasal symptoms and suppressed TDI-induced upregulations of H1R and IL-4 gene expressions in TDI-sensitized rats. These data suggest that (?)-maackiain is a novel antiallergic compound that alleviates nasal symptoms in TDI-sensitized allergy model rats through the inhibition of H1R and IL-4 gene expression. The molecular mechanism underlying its suppressive effect for H1R gene expression is mediated by the inhibition of PKCδ activation.

Heck-oxyarylation of 2-phenyl-2H-chromenes and 1,2-dihydronaphthalenes

The Heck-oxyarylation of racemic 2-phenyl-2H-chromene [(±)-4b] and 1 2-dihydronaphthalenes (14a,b) has been studied with 2-chloromercuriphenols (5a-d) in the presence of Li2[PdCl4] catalyst The reactions resulted in the diastereoselective formation of rac

(±)-3,4-Dihydroxy-8,9-methylenedioxypterocarpan and derivatives: Cytotoxic effect on human leukemia cell lines

Naturally occurring pterocarpans 1a,b, pterocarpan 1c, isoflavane 2 and ortho-quinone 3 were synthesized in the racemic form and their cytotoxic effect was evaluated on the human leukemia cell lines K562 (resistant to oxidative stress), Lucena-1 (MDR phenotype) and HL-60. Ortho-quinone 3 (IC50 = 1.5 μM, 1.8 μM and 0.2 μM, respectively) and catechol pterocarpan 1a (IC50 = 3.0 μM, 3.7 μM and 2.1 μM, respectively) were the most active compounds on these cells and were also evaluated on other human leukemia cell lines (Jurkat and Daudi). Ortho-quinone 3 was 2 to 10 times more potent than pterocarpan 1a, depending on the cell line considered, however, showed a greater toxicity for lymphocytes activated by PHA.

Synthesis and preliminary pharmacological evaluation of coumestans with different patterns of oxygenation

Five coumestans with different patterns of oxygenation in rings A and D were synthesized from resorcinol and aromatic aldehydes, and screened for their antimyotoxic activity. The most potent compound (2b, IC50 = 1 μM) was selected for study of

Absolute configuration and total synthesis of (-)-cabenegrin A-I

The total synthesis of (-)-cabenegrin A-I [(-)-1] in five steps was achieved from (-)-6aR, 11aR-maackiain [(-)-5], which in turn was prepared by the optical resolution of racemic (±)-5 using S-(-)α-methylbenzyl isocyanate as the the chiral auxiliary. The homochirality of(-)-maackiain [(- )-5] and (-)cabenegrin A-I [(-)-1] was proved by CD measurements. Synthesis of (±)maackiain [(±)-5] is also presented, starting from the readily available phenol derivatives resorcinol and sesamol, which demonstrates the synthetic utility of the Heck-type oxyarylation process for obtaining pterocarpane derivatives on a multigram scale. A new ring-opening reaction of pterocarpanes (7 → 28) is described.

SYNTHESIS OF (+/-)-CABENEGRINS A-I AND A-II

(+/-)-Cabenegrins A-I and A-II, the potent antidotes against snake venoms, have been synthesized from maakiain (9) and 2-carbomethoxy-3-benzyl maakiain (20).

Structure and Synthesis of Isoflavonoid Analogues from Neorautanenia amboensis Schinz

The isolation and structural elucidation of six pterocarpans: neorautenane, neorautanol, edulenane, edulenanol, ambonane, and neorautenanol, as well as two new isoflavanones: ambonone and neoraunone, are reported.The structures of neorautenane and neoraut