81378-06-5

Upstream product

• 108-31-6 maleic anhydride 
• 142-45-0 Acetylenedicarboxylic acid 

Downstream Products

• 1340541-41-4 1,4-bis-(3,5-dibezylidene-4-oxo-piperidin-1-yl)-but-2-yne-1,4-dione 
• 881653-06-1 cyclohexa-1,4-diene-1,2-dicarbonyl dichloride 

Relevant academic research and scientific papers

Dimeric 3,5-bis(benzylidene)-4-piperidones: A novel cluster of tumour-selective cytotoxins possessing multidrug-resistant properties

A series of bis[3,5-bis(benzylidene)-4-oxo-1-piperidinyl]amides 1 display potent cytotoxic properties towards a wide range of tumours. A number of the CC50 and IC50 values are in the range of 10-8 M. Specifically, these compounds have the following important properties. First, greater toxicity was demonstrated towards certain tumours than various non-malignant cells. Second, various compounds in series 1 are toxic to a number of human colon cancer and leukaemic cells. Third, these compounds reverse P-gp mediated multidrug resistance. Various prototypic molecules such as 1a,b and 1i were identified as lead molecules for further studies. A representative lead molecule 1b induces apoptosis via internucleosomal DNA fragmentation and PARP cleavage in HSC-2 and HL-60 cells while flow cytometry revealed that this compound blocked the G2/M and S-phases in the cell cycle of human colon cancer HCT-116 cells.

Bis[3,5-bis(benzylidene)-4-oxo-1-piperidinyl]amides: A Novel Class of Potent Cytotoxins

The principal objective of this study was the examination of the theory of cytotoxic synergism. In this exploratory study, we tested the hypothesis that doubling the number of sites available for thiol alkylation in a series of candidate cytotoxins increases potency more than two-fold. This concept was verified in one-third of our comparisons using human Molt 4/C8 and CEM T-lymphocytes and murine L1210 cells. In addition, the significant potencies of various members of our compound series justified further studies. Molecular modeling revealed that relative locations of the amidic groups correlate with cytotoxicity. A potent cytotoxic compound, 1,2-bis(3,5-dibenzylidene-4-oxo-piperidin-1-yl)ethane-1,2-dione (1a) inhibited the growth of a large number of human tumor cell lines and displayed greater toxicity toward certain non-adherent cells than toward adherent neoplasms or fibroblasts. The mode of action of 1a includes induction of apoptosis and necrosis.

Diastereoselection in the formation of spirocyclic oxindoles by the intramolecular heck reaction

Diastereoselective double Heck cyclizations of cyclohexene diamides 1 and 3 form contiguous quaternary stereocenters, with diastereoselection being controlled by the trans-diol protecting group. In this, the first in a series of two papers, the origin of

Polynuclear nonfused bis(1,3,4-oxadiazole)-containing systems

Nonfused bis-1,3,4-oxadiazoles were synthesized by reaction of 5-substituted mono- and bis-tetrazoles with mono- and dicarboxylic acid chlorides. The results of kinetic studies showed that the transformation of tetrazoles into 1,3,4-oxadiazoles is accelerated by 1 to 2 orders of magnitude on addition of a catalytic amount of dimethylformamide, triethylamine, or pyridine. Pleiades Publishing, Inc., 2006.

Preparation and photolysis of diaryl esters of acetylenedicarboxylic acid

Two diaryl acetylenedicarboxylates 1 a,b have been prepared in moderate yields by direct reaction of acetylenedicarboxylic acid with the corresponding phenols catalyzed by sulfuric or p-toluenesulfonic acids and also through acetylenedicarbonyl chloride. The accompanying by-products have been characterized. Attempted esterification using N,N'-dicyclohexylcarbodiimide as condensing agent gives an asymmetric ester amide 11a and a substituted uracil 12a. Photolysis of the aryl ester 1 a,b in benzene solution affords the benzocoumaran-3-ones 14 a,b. In the case of 1b, minor amounts of a polycyclic condensed 4-chromanone 17b have also been observed. These results show that the nature of the substituent attached at the β-position of the C ≡ C triple bond plays an important role in the cyclization of o-hydroxyaryl ethynyl ketones.

Acetylenedicarbonyl Dichloride

In situ prepared carbonyl chloride 2 can be used as activated acetylenedicarboxylic acid in Diels-Alder syntheses.