109529-99-9

Upstream product

• 1794-46-3 ((1E,3E)-5-chloropenta-1,3-dien-1-yl)benzene 
• 122-52-1 triethyl phosphite 
• 109529-98-8 ((1E,3E)-5-bromopenta-1,3-dien-1-yl)benzene 
• 1067-87-4 Diethyl allylphosphonate 
• 102-92-1 cinnamoyl chloride 
• 38447-05-1 (2E,4E)-methyl 5-phenylpenta-2,4-dienoate 
• 13466-40-5 (2E, 4E)-5-phenylpenta-2,4-dienal 
• 14371-10-9 (E)-3-phenylpropenal 
• 1357009-95-0 diethyl {2-[(1-phenyl-1H-tetrazol-5-yl)sulfonyl]ethyl}phosphonate 
• 5324-30-1 diethyl 2-bromoethylphosphonate 
• 58506-33-5 5-phenyl-trans,trans-2,4-pentadien-1-ol 
• 28010-12-0 5-phenylpenta-2,4-dienoic acid 

Downstream Products

• 128368-81-0 21-[4-((1E,3E,5E)-6-Phenyl-hexa-1,3,5-trienyl)-phenyl]-henicosanoic acid methyl ester 
• 134171-71-4 Dimethyl-{22-[4-((1E,3E,5E)-6-phenyl-hexa-1,3,5-trienyl)-phenyl]-docosyl}-amine 
• 128368-79-6 21-[4-((1E,3E,5E)-6-Phenyl-hexa-1,3,5-trienyl)-phenyl]-henicosanoic acid 
• 128368-78-5 1-palmitoyl-2-(21-diphenylhexatrienyl-henicosanoyl)-sn-glycero-3-phosphocholine 
• 134171-65-6 Trimethyl-{22-[4-((1E,3E,5E)-6-phenyl-hexa-1,3,5-trienyl)-phenyl]-docosyl}-ammonium; iodide 
• 1261552-49-1 C₃₀H₄₂OSi 
• 1261552-48-0 C₂₈H₃₈OSi 

Relevant academic research and scientific papers

Developing glutathione-activated catechol-type diphenylpolyenes as small molecule-based and mitochondria-targeted prooxidative anticancer theranostic prodrugs

Developing concise theranostic prodrugs is highly desirable for personalized and precision cancer therapy. Herein we used the glutathione (GSH)-mediated conversion of 2,4-dinitrobenzenesulfonates to phenols to protect a catechol moiety and developed stable pro-catechol-type diphenylpolyenes as small molecule-based prooxidative anticancer theranostic prodrugs. These molecules were synthesized via a modular route allowing creation of various pro-catechol-type diphenylpolyenes. As a typical representative, PDHH demonstrated three unique advantages: (1) capable of exploiting increased levels of GSH in cancer cells to in situ release a catechol moiety followed by its in situ oxidation to o-quinone, leading to preferential redox imbalance (including generation of H2O2 and depletion of GSH) and final selective killing of cancer cells over normal cells, and is also superior to 5-fluorouracil and doxorubicin, the widely used chemotherapy drugs, in terms of its ability to kill preferentially human colon cancer SW620 cells (IC50 = 4.3 μM) over human normal liver L02 cells (IC50 = 42.3 μM) with a favourable in vitro selectivity index of 9.8; (2) permitting a turn-on fluorescent monitoring for its release, targeting mitochondria and therapeutic efficacy without the need of introducing additional fluorophores after its activation by GSH in cancer cells; (3) efficiently targeting mitochondria without the need of introducing additional mitochondria-directed groups.

Synthesis of conjugated polyenes via sequential condensation of sulfonylphosphonates and aldehydes

Selective metalation of sulfonylphosphonates results in sufficiently stable carbanions that undergo chemoselective Julia-Kocienski condensation with various aldehydes to provide (E)-allylic phosphonates in good yields and selectivities. The subsequent Horner-Wadsworth-Emmons condensation with aldehydes is used to synthesize various unsymmetrical trans-dienes, trienes, and tetraenes. This methodology is utilized for the concise synthesis of a naturally occurring fluorescent probe for membrane properties, β-parinaric acid.

PALLADIUM-CATALYZED ARYLATION OF DIETHYL ALLYLPHOSPHONATE

A method was developed for palladium-catalyzed arylation of diethyl allylphosphonate by aryl iodides and aromatic and hetrocyclic carboxylic acid chlorides in tertiary amines.The possibility of arylation in aqueous organic media was also demonstrated.The optimum conditions were found for the production of both γ-arrylallyl or γ-heterylallylphosphonates and (arylmethyl)vinylphosphonates in the individual state.

SYNTHESIS OF FLUORESCENT PROBES FOR LOCALIZED MEMBRANE FLUIDITY MEASUREMENTS

The synthesis of two long-chain homologues of the fluorescent membrane probes TMA-DPH and DPHpPC is described.The long-chain phosphatidylcholine could be synthesized from palmitoyl-lysophosphatidylcholine and 21-(diphenylhexatrienyl)henicosanoic acid only when the promoting agent was 1,1'-thionyldiimidazole.

1,1'-Thionyldi-imidazole in the synthesis of a long-chain phospholipidic membrane probe

A long-chain fluorescent membrane probe could be synthesized from palmitoyl-lysophosphatidylcholine and 21-(diphenylhexatrienyl)henicosanoic acid only when the promoting agent was 1,1'-thionyldi-imidazole.