101109-88-0

Basic information

• Product Name: α,α'-bis(thiophen-3-ylmethylene)cyclohexanone
• Synonyms: α,α'-bis(thiophen-3-ylmethylene)cyclohexanone
• CAS NO: 101109-88-0
• Molecular Weight: 286.419
• Mol File: 101109-88-0.mol

Chemical Properties

• CAS DataBase Reference: α,α'-bis(thiophen-3-ylmethylene)cyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: α,α'-bis(thiophen-3-ylmethylene)cyclohexanone(101109-88-0)
• EPA Substance Registry System: α,α'-bis(thiophen-3-ylmethylene)cyclohexanone(101109-88-0)

Safety Data

• Hazardous Substances Data: 101109-88-0(Hazardous Substances Data)

Upstream product

• 498-62-4 3-thiophene carboxaldehyde 
• 108-94-1 cyclohexanone 

Relevant articles and documents

Synthesis of diarylidenecyclohexanone derivatives as potential anti-inflammatory leads against COX-2/mPGES1 and 5-LOX

Inflammation is a pathophysiological condition which progresses through the prostaglandin (PG) and leukotriene (LT) pathways channelized by the enzymes COX/mPGES1 and 5-LOX respectively. Diarylidenecyclohexanone (DAC) derivatives (Ia-j, IIa-c, IIIa and IVa) were synthesized, characterized and screened for their in vitro anti-inflammatory activity via inhibition of 5-LOX and COX-2/mPGES1 enzymes. Compound Ic inhibited PGE2 production exhibiting an IC50 of 6.7 ± 0.19 μM, comparable to the standard inhibitor, licofelone (IC50 of 5.4 ± 0.02 μM). Compounds Ie and Ig showed maximum in vitro inhibitory activity against 5-LOX, exhibiting an IC50 of 1.4 ± 0.1 μM and 1.5 ± 0.13 μM, respectively, and these are comparable to that of the standard drug, zileuton (IC50 = 1.2 ± 0.11 μM). Ie and Ig do not possess radical scavenging properties and may not be disrupting the redox cycle of the enzyme. Hence they may be inhibiting the enzyme by a competitive mode. One of the compounds in the DAC series (IIc) containing a heterocyclic thienyl ring inhibited all the three enzymes. It inhibited 5-LOX and COX-2/mPGES1 with an IC50 of 1.8 ± 0.12 μM and 7.5 ± 0.4 μM respectively. An RT-PCR based mRNA expression study highlighted that Ic predominantly inhibited the expression of COX-2 rather than mPGES1. No toxicity towards the HeLa cell line indicated that the DACs could serve as structural templates towards lead optimization of compounds for discovery of novel, potent, safe and affordable drugs as anti-inflammatory agents.

The products of the reaction between 6-amine-1,3-dimethyl uracil and bis-chalcones induce cytotoxicity with massive vacuolation in HeLa cervical cancer cell line

As a part of our research in the chemistry of chalcones we have prepared four pyrimidine monoadducts of bis-chalcones through the reaction with 6-amino-1,3-dimethyl uracil. These compounds displayed cytotoxicity with a massive vacuolation in different human cell lines in vitro. Compound 6 was the most cytotoxic inducer of vacuoles, this compound induced G1 phase cell cycle arrest, and their cytotoxicity went without morphological and biochemical evidence of apoptotic cell death in HeLa cells. In addition, our results showed that this vacuole formation does not require de novo protein synthesis and the content vacuolar is acidic. Compound 6 induce necrotic cell death with excessive vacuolation, similar to a process of autophagy. Spautin-1 an inhibitor of autophagy, decreased the transformation of microtubule-associated protein 1 light chain 3 (LC3B-I) to LC3B-II and the vacuolation induced by compound 6 in HeLa cells, both autophagy processes. These compounds could be of pivotal importance in the study of non-apoptotic cell death with vacuole formation and could be useful in research into new autophagy inhibitors agents.

Synthesis, mechanistic and synergy studies of diarylidenecyclohexanone derivatives as new antiplasmodial pharmacophores

Diarylidenecyclohexanone (DAC) derivatives (Ia-i, IIa-c and IIIa-b) were synthesized, characterized and screened for their invitro antiplasmodial activities against erythrocytic stages of chloroquine (CQ) sensitive and resistant strains of P. falciparum by using SYBR green I fluorescence assay. SAR studies of DAC derivatives showed antiplasmodial activity in the order of 3-NO2 (Ib, IC50 0.95 μM) > 3-chloro (Id, IC50 3 μM) > 4-chloro (Ie, IC50 8.5 μM) > 2-chloro (Ic, IC50 13 μM). Further Ib and Id exhibited nearly equal potencies against CQ-resistant strains P. falciparum Dd2, {IC50 1 μM (Ib) and 2.7 μM (Id)} and PfINDO {IC50 1.1 μM (Ib) and 2.5 μM (Id)}. Drug exposure followed by drug withdrawal-based stage-specific kill kinetic studies showed that Ib is shizonticidal within 3 h while the earliest killing actions against Trophozoites and Rings were seen at >3 h and >6 h, respectively. Combination studies of the most potent leads viz. Ib and Id showed strong to moderate synergistic effects with Artemisinin (?FIC50: 0.34 to 0.63) whereas no interaction (?FIC50: 0.65 to 2.36) was observed with Chloroquine. The DACs showed significant insilico binding affinity with β-haematin and P. falciparum lactate dehydrogenase (PfLDH) suggesting these to be the targets of their antiplasmodial action. High compliance with Lipinski rule of 5 and high selectivity index of Ib (105.3) and Id (8.3) against HeLa cell line indicated that Diarylidenecyclohexanones could serve as structural templates towards lead optimization of compounds for discovery of novel, potent, safe and affordable drugs against malaria.

Chemoselective Claisen-Schmidt bis-substitutional condensation catalyzed by an alkoxy-bridged dinuclear Ti(IV) cluster

The highly efficient and chemoselective α,α′-bis-substitution of alkanones is important in organic synthesis. Herein, a dimeric titanium cluster, Ti2Cl2(OPri)6·2HOPri (Ti2), is used in the Claisen-Schmidt condensation reaction, for the selectively activation of symmetrical ketones containing α,α′-methylene groups and production of α,α′-bis-substituted alkanones in high efficiency and chemoselectivity. The high efficiency and chemoselectivity can be extended to a variety of typical alkanones and aromatic aldehydes. Both of the oxo-bridged dimeric motif of Ti2 and the ionic Ti-Cl bond are responsible for the high efficiency and chemoselectivity.