94386-22-8

Basic information

• Product Name: 2,6-bis(1H-pyrrol-2-ylmethylene)cyclohexan-1-one
• Synonyms: 2,6-bis(1H-pyrrol-2-ylmethylene)cyclohexan-1-one;2,6-Bis(1H-pyrrol-2-ylmethylene)cyclohexanone
• CAS NO: 94386-22-8
• Molecular Formula: C16H16N2O
• Molecular Weight: 252.31104
• EINECS: 305-244-4
• Mol File: 94386-22-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 555.7°Cat760mmHg
• Flash Point: 281.1°C
• Appearance: /
• Density: 1.292g/cm³
• Vapor Pressure: 2.19E-12mmHg at 25°C
• Refractive Index: 1.73
• CAS DataBase Reference: 2,6-bis(1H-pyrrol-2-ylmethylene)cyclohexan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-bis(1H-pyrrol-2-ylmethylene)cyclohexan-1-one(94386-22-8)
• EPA Substance Registry System: 2,6-bis(1H-pyrrol-2-ylmethylene)cyclohexan-1-one(94386-22-8)

Safety Data

• Hazardous Substances Data: 94386-22-8(Hazardous Substances Data)

Usage

General Description

2,6-bis(1H-pyrrol-2-ylmethylene)cyclohexan-1-one is a chemical compound with the molecular formula C22H18N2O. It is a derivative of cyclohexanone, with two 1H-pyrrole-2-carbaldehyde groups attached to the cyclohexane ring. 2,6-bis(1H-pyrrol-2-ylmethylene)cyclohexan-1-one has potential uses in organic synthesis and material science due to the presence of the pyrrole moiety, which imparts unique properties and reactivity. It may also have applications in medicinal chemistry as a building block for the synthesis of biologically active compounds. The exact properties and potential uses of 2,6-bis(1H-pyrrol-2-ylmethylene)cyclohexan-1-one are still being investigated by researchers in various fields of chemistry.

InChI:InChI=1/C16H16N2O/c19-16-12(10-14-6-2-8-17-14)4-1-5-13(16)11-15-7-3-9-18-15/h2-3,6-11,17-18H,1,4-5H2/b12-10+,13-11+

Upstream product

• 1003-29-8 2-pyrrole aldehyde 
• 108-94-1 cyclohexanone 

Relevant articles and documents

Molecular Structure and Photoinduced Intramolecular Hydrogen Bonding in 2-Pyrrolylmethylidene Cycloalkanones

The structures of pyrrolylmethylidene derivatives of 2,3-dihydro-1H-inden-1-one (3), 3,4-dihydro-naphthalen-1(2H)-one (4), and cycloalkanones (5-7) were studied for the first time in the solid state and solution by NMR, IR, and UV spectroscopies supported

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.