30343-70-5

Usage

Uses

Used in Pharmaceutical Industry:
Dihydroxythiobinupharidine is used as a bioactive compound for its potential therapeutic applications. Its multiple activities suggest that it could be a promising candidate for the development of new drugs targeting various health conditions.
Used in Cancer Research:
Dihydroxythiobinupharidine is used as a potential anticancer agent due to its bioactive properties. It may be investigated for its ability to modulate oncological signaling pathways, inhibit tumor growth, and enhance the efficacy of conventional chemotherapeutic drugs.
Used in Drug Delivery Systems:
To improve the delivery, bioavailability, and therapeutic outcomes of Dihydroxythiobinupharidine, it can be incorporated into novel drug delivery systems. Various organic and metallic nanoparticles can be employed as carriers for its delivery, aiming to enhance its overall effectiveness in treating specific health conditions.

Biochem/physiol Actions

6,6′-Dihydroxythiobinupharidine inhibits NFκB activation, leading to an induction of apoptosis via cleavage of procaspase-9 and poly (ADP-ribose) polymerase (PARP). It was also found to act synergistically with cytotoxic drugs such as cisplatin and etoposide, enabling their cytotoxic effect at lower concentrations. 6,6′-Dihydroxythiobinupharidine was found to have cytotoxic activity at a concentration of ~10 μM on human leukemia cells (U937), mouse melanoma cells (B16F10), and human fibroblasts (HT1080).In addition, Nuphar lutea extract was effective against both Leishmania promastigote and amastigote forms (IC50?=?2?±?0.12?μg/mL; ID50?=?0.65?±?0.023?μg/mL; LD50?=?2.1?±?0.096?μg/mL, STI?=?3.23). A synergistic antileishmanial activity was demonstrated with the antileishmanial drug, paromomycin.Recently 6,6′-dihydroxythiobinupharidine was found to be active against MRSA and VRE strains with an MIC of 1-4?μg/mL. Inhibition of DNA topoisomerase?IV but not DNA gyrase in S.?aureus was suggested as the mechanism of action. 6,6′-Dihydroxythiobinupharidine was also shown to promote neutrophil effector bactericidal functions.

Upstream product

• 1418134-80-1 C₁₅H₂₀NO⁽¹⁺⁾*C₂F₃O₂^(1-) 
• 60161-30-0 4-(furan-3-yl)-1-methyl-7-methyleneoctahydro-2H-quinolizine 

Downstream Products

• 30343-72-7 thiobinupharidine 

Relevant academic research and scientific papers

Total Syntheses and Biological Evaluation of Both Enantiomers of Several Hydroxylated Dimeric Nuphar Alkaloids

Herein, we describe the first total syntheses of five members of the dimeric nuphar alkaloids: (+)-6,6′-dihydroxythiobinupharidine (+)-1a, (+)-6-hydroxythiobinupharidine (+)-1-b, (-)-6,6′-dihydroxythionuphlutine (-)-2-a, (-)-6,6′-dihydroxyneothiobinupharidine (-)-3a, and (+)-6,6′-dihydroxyneothionuphlutine (+)-4-a. The latter two have not been found in nature. We have also made each of their enantiomers (-)-1a-b, (+)-2a, (+)-3a, and (-)-4a. The key step in these syntheses was the dimerization of an α-aminonitrile (a hydrolytically stable surrogate for its corresponding hemiaminal) with chiral Lewis acid complexes. We have also reassigned the literature structures of (+)-1-a-1b - for those instances in which the NMR spectra were obtained in CD3OD - to their corresponding CD3O-adducts. Our efforts provide for the first time apoptosis data for (-)-3a, (+)-4a, and all five non-natural enantiomers prepared. The data indicate high apoptotic activity regardless of the enantiomer or relative stereochemical configuration at C7 and C7′. Nuphars are speedy killers: For the first time several of the hydroxylated dimeric nuphar alkaloids and their unnatural enantiomers have been synthesized. First-ever apoptosis data for many of these compounds is provided.

Crude drugs from aquatic plants. VI. On the alkaloid constituents of Chinese Nupharis Rhizoma, the dried rhizoma of Nuphar pumilum (TIMM.) DC. (Nymphaceae) : Structures and rearrangement reaction of thiohemiaminal type nuphar alkaloids

From Chinese Nupharis Rhizoma, the dried rhizoma of Nuphar pumilum (TIMM.) DC. (Nymphaceae), four thiohemiaminal type nuphar alkaloids with potent immuno-suppressive activity, 6-hydroxythiobinupharidine, 6,6′-dihydroxythiobinupharidine, 6-hydroxythionuphlutine B, 6′-hydroxythionuphlutine B, have been isolated together with nine inactive nuphar alkaloids. The configurations of the 6- and 6′-hydroxyl groups in those thiohemiaminal type nuphar alkaloids were confirmed on the basis of their 2D-NMR analysis. During the course of chemical elucidation of those thiaspirane type dimeric sesquiterpene alkaloids, new rearrangement reaction of the thiaspirane ring in thiohemiaminal type alkaloids with 6-hydroxyl group was found and the reaction pathway was discussed. By using this rearrangement reaction, 6-hydroxythionuphlutine B was chemically related with 6-hydroxythiobinupharidine, so that the absolute stereostructures of thionuphlutine B and its related compounds such as 6-hydroxythionuphlutine B, 6′-hydroxythionuphlutine B, and thionuphlutine B β-sulfoxide, were characterized.