140401-72-5

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 502-42-1 cycloheptanone 
• 6275-32-7 (2E,6E)-2,6-bis(4-methoxybenzylidene)cyclohexanone 

Downstream Products

• 888724-09-2 2,7-bis-(4-methoxy-phenyl)-1,6-dioxa-dispiro[2.1.2.4]undecan-4-one 
• 1442980-38-2 C₂₉H₃₀N₂O₄S 
• 1442980-64-4 C₂₇H₂₈N₂O₂S 
• 1442980-80-4 C₃₀H₃₂N₂O₄S 
• 103381-48-2 2,7-Dibromo-2,7-bis-[bromo-(4-methoxy-phenyl)-methyl]-cycloheptanone 
• 888724-21-8 4a-hydroxy-9-[hydroxy-(4-methoxyphenyl)methyl]-5-(4-methoxyphenyl)-4,4a,5,6,7,8-hexahydro-1-thia-3a,10-diaza-cyclohepta[f]inden-3-one 
• 888724-15-0 4a-hydroxy-9-[hydroxy-(4-methoxy-phenyl)-methyl]-4-(4-methoxy-phenyl)-1,3,4,4a,5,6,7,8-octahydro-cycloheptapyrimidine-2-thione 
• 102560-25-8 2,7-bis-(4-methoxy-benzyl)-cycloheptatrienone 

Relevant academic research and scientific papers

Synthesis and antitumor activity of certain new thiazolo[2,3-b]quinazoline and thiazolo[3,2-a]pyrimidine analogs

A novel series of thiazolo[2,3-b]quinazoline (16-19, 25-28, and 34-37) and cyclohepta[d]thiazolo[3,2-a]pyrimidine (20-23, 29-32, and 38-41) analogs was designed and synthesized. Structure elucidation of the synthesized compounds was attained by the use of H1 NMR, C13 NMR, and mass spectrometry. The obtained compounds were evaluated for their in vitro antitumor activity using the National Cancer Institute's 60 cell lines' panel assay that included nine tumor subpanels, namely, leukemia, non-small cell lung, colon, CNS, melanoma, ovarian, renal, prostate, and breast cancer cells. Most of the investigated compounds showed a remarkable broad-spectrum antitumor activity. Compounds 19, 28, 32, and 34 proved to be 10-, 15-, 2-, and 7-fold more active than 5-FU, with GI50 MG-MID values of 2.4, 1.5, 11.2, and 3.1 μM, respectively.

Synthesis and biological evaluation of new curcumin derivatives as antioxidant and antitumor agents

Twenty-four new compounds were prepared, taking curcumin as a lead, in order to explore their antioxidant and antitumor properties. The capacities of these derivatives to scavenge the 2,2′-azinobis(3-ethylbenzothiazoline-6- sulfonic acid) radical cation (ABTS.+), and to protect human red blood cells (RBCs) from oxidative haemolysis were investigated. In addition, the percentage viability of different cell lines (Hep G2, WI38, VERO and MCF-7) was tested. The result of the antitumor testing was generally in accordance with those of the antioxidant assays. Compounds which bear o-methoxy substitution to the 4-hydroxy function in the phenyl ring (7g, 5g and 3g) exhibited significantly higher ABTS.+-scavenging, antihaemolysis, and antitumor activities than other derivatives. In addition, molecular modelling studies were carried out for biologically active and inactive compounds, to study the structure-activity relationship, with the aim to elucidate which portions of the molecules are critical for the antioxidant and antitumor activity.

A facile synthesis of α,α′-(EE)-bis(benzylidene)-cycloalkanones and their antitubercular evaluations

An economical and facile synthesis of α,α′-(EE)-bis(benzylidene)-cycloalkanones was achieved by the reaction of cycloalkanones with different aromatic aldehydes using ethanolic KOH in good yields. Few of the selected compounds were reduced with NaBH4 to the respective α,α′-(EE)-bis(benzylidene)-cycloalkanols. All these compounds and our earlier synthesized cyclohexyl phenyl methanols were evaluated for their antitubercular, antifungal and antibacterial activities. Several compounds displayed moderate antitubercular activity with MIC = 12.5-1.56 μg/mL. However, none of the compounds displayed any significant antifungal activity.

Synthesis of Curcumin Analogues as Potential Antioxidant, Cancer Chemopreventive Agents

New series of 3,5-bis(substituted benzylidene)-4-piperidones, 2,7-bis(substituted benzylidene)cycloheptanones, 1,5-bis(substituted phenyl)-1,4-pentadien-3-ones, 1,7-bis(substituted phenyl)-1,6-heptadien-3,5-diones, 1,1-bis(substituted cinnamoyl)-cyclopentanes, and 1,1-bis(substituted cinnamoyl)cyclohexanes have been synthesized and tested for their antioxidant activity. Among the tested compounds, compounds II 4, II9 II10, II11, V1, and V4 exhibited higher free radical scavenger activity with % inhibition values of 90.71, 91.24, 96.91, 94.26, 99.23, and 99.85%, respectively. Moreover, compound V1 is the safest member toward peripheral multinuclear neutrophils (PMNs) with a % viability value of 91%. Detailed synthesis, spectroscopic, and biological data are reported.

The synthesis and chlorosulfonation of some diarylidene and heteroarylidene ketones with varying alicyclic ring size

A series of diarylidene and heteroarylidene ketones (1-20) was prepared using alicyclic ketones ((CH2)nC=O where n=3 to 7).An improved synthesis of 2,4-dibenzylidenecyclobutanone (1) is described and the ease of preparation of the arylidene derivatives is considered in terms of the size of the alicyclic ring.Treatment of 2,5-dibenzylidenecyclopentanone (2) with chlorosulfonic acid (10 mole equivalents) afforded the 4,4'-bis-sulfonyl chloride (23), reducing the amount of chlorosulfonis acid (6 mole equivalents) produced the corresponding mono-sulfonyl chloride (24).Only the respective 4,4'-bis-sulfonyl chlorides (39, 45, 51) could be isolated from the diarylidene ketones derived from larger alicyclic rings.Attempted chlorosulfonation of 2,4-dibenzylidene cyclobutanone (1) gave a mixture of products which could not be clearly characterised.The sulfonyl chlorides were converted into stable sulfonamides (25-29, 35, 36, 38, 40-44, 46-48, 52, 54) by condensation with amines, and selected samples were screened for biological activity as potential insecticides, herbicides, and fungicides.The orientation of sulfonation is discussed in relation to stereoelectronic factors and the relevant spectral data.Key words: Arylidene and heteroarylidene ketones, chlorosulfonation, sulfonamides

Mesomorphic Behavior of 2,4-Bis-(4-alkoxybenzylidene)cyclopentanones and Related Compounds

The mesomorphic properties of homologous series of 2,5-bis(4-alkoxybenzylidene)cyclopentanones, 2,6-bis(4-alkoxybenzylidene)cyclohexanones, and 2,7-bis(4-alkoxybenzylidene)cycloheptanones have been compared with each other.The clearing point is markedly depressed by increasing the size of the cycloalkanone ring.The cyclopentanone derivatives carrying the methoxy to pentyloxy groups are purely nematogenic, the next member exhibits a smectic A phase as well as a nematic phase.Smectic A and C phases are observed for the heptyloxy and octyloxy homologues, and only a smectic C phase for the later members.In both the cyclohexanone and cycloheptanone derivatives, the methoxy to decyloxy homologues exhibit a nematic phase and the higher members exhibit a smectic C phase.In addition, a smectic A phase appears in the nonyloxy and decyloxy homologues of the cyclohexanone series. - Keywords: nematic, smectic C, cycloalkanones, nonlinear molecules

New Aziridines and Pyrazolines Derived from Diarylidenecycloalkanones

A number of diarylidenecycloalkanones (I and II) have been prepared by the condensation of cycloalkanones with different aromatic aldehydes.Treatment of I and II with bromine gives the corresponding tetrabromides (III and IV).Compounds III react with meth