Anti-Inflammatory Effect of 3-Methylcarbazoles on RAW 264.7 Cells Stimulated with LPS, Polyinosinic-Polycytidylic Acid and Pam3CSK

ABSTRACT In the present study, 3-methylcarbazole and 1-methoxy-3-methylcarbazole were isolated from the culture of Streptomyces sp. LJK109, endophyte of Alpinia galanga Swartz. 3-methylcarbazole, a carbazole derivative, has been found to be highly potent as anti-inflammatory agent. The immunomodulatory activity of these agents in toll like receptor (TLR)-activated RAW 264.7 macrophages induced by lipopolysaccharide (LPS), Poly(I:C), and pam3CSK was investigated by assessing nitric oxide (NO) and pro-inflammatory cytokines. The 3-methylcarbazoles dose-dependently suppressed the release of NO, PGE 2 , TNF-α, IL-1β, IL-6 and IL-10 in LPS-and pam3CSK-activated macrophages but not in Poly(I:C)-activated macrophages. Our results suggest that 3-methylcarbazoles can be further developed as a promising anti-inflammatory remedy

Synthesis of 3-indolylacetamide derivatives and evaluation of their plant growth regulator activity

Some 3-indolyl acetamide derivatives were synthesised via the coupling of indole-3-acetic acid (IAA) with aminobenzene derivatives and were screened for their plant growth regulator activities on rice seedling. The results show that some of the compounds synthesised possess considerable growth promoting activities in the concentration range of 1.7-0.17 ppm compared to IAA

Synthesis of spirocyclopente-dione anthracene adduct, precursor of the cyclopentenone prostagladins via ring-closing metathesis reaction

A synthesis of the spirocyclopente-dione anthracene adduct, a precursor of the cyclopentenone prostaglandins has been reported. The synthesis involved a Diels-Alder reaction of anthracene and dimethyl fumarate to afford 3 followed by reduction, oxidation and esterification reactions to provide methyl ester anthracene adduct 8, which further converted to the the allylic alcohol (12). Then, Ring-Closing Metathesis (RCM) reaction afforded the cyclopentenol anthracene adduct, which after oxidation provided the spirocyclopente-dione anthracene adduct in good yields

Stereoselective synthesis of α-methylenecyclopentenones via a Diels-Alder/retro-Diels-Alder protocol

A new procedure for the stereoselective synthesis of cross-conjugated dienones is reported. This method makes use of the Diels–Alder adduct of anthracene and dimethyl fumarate, a precursor to a spirocyclopent-2-enone anthracene adduct as the key intermediate. The addition of propyllithium or octyllithium to the key intermediate followed by a retro-Diels–Alder reaction furnished α-methylenecyclopentenones bearing a γ-propyl or γ-octyl side chain, respectively, in moderate yields and as single geometric isomers

Studies of stereo-selective cyclo-additions and transformations of substituted 2-cyclopenten-1-one with chiral anthracene templates

The chiral (S)-9-(1-methoxyethyl), (R)-9-(1,2-dimethoxyethyl) and 9-(1R, 2R)-(1,2-dimethoxypropyl) anthracenes were synthesised and used for the thermal Diels-Alder reaction with cyclopentene-3,5-dione. Unlike the maleic anhydride and N-substituted malemides, the cyclo-adducts were obtained with high regio-selectivity as a single diastereomer. The X-ray structure of the cyclo-adduct showed an enol form but the 13C NMR showed resonances for two cyclopentanone carbonyl groups suggesting the solution structure is in the diketone form. Stereo-controlled studies using organomagnesium additions to the carbonyl groups resulted in hydrolytic cleavage of the enol ether and elimination of water to give β-alkylketone anthracene adducts. These were unsuccessful in preparing chiral cyclopentenone core structures

Stereoselective synthesis of α-methylenecyclopentenones via a Diels-Alder/retro-Diels-Alder protocol

A new procedure for the stereoselective synthesis of cross-conjugated dienones is reported. This method makes use of the Diels-Alder adduct of anthracene and dimethyl fumarate, a precursor to a spirocyclopent-2-enone anthracene adduct as the key intermed

2,5-Diketopiperazine Derivatives as Potential Anti-Influenza (H5N2) Agents: Synthesis, Biological Evaluation, and Molecular Docking Study

2,5-Diketopiperazine derivatives, consisting of benzylidene and alkylidene substituents at 3 and 6 positions, have been considered as a core structure for their antiviral activities. Herein, the novel N-substituted 2,5-Diketopiperazine derivatives were successfully prepared and their antiviral activities against influenza virus were evaluated by monitoring viral propagation in embryonated chicken eggs. It was found that (3Z,6Z)-3-benzylidene-6-(2-methyl propylidene)-4-substituted-2,5-Diketopiperazines (13b–d), (3Z,6E)-3-benzylidene-6-(2-methylpropyli dene)-1-(1-ethyl pyrrolidine)-2,5-Diketopiperazine (14c), and Lansai-C exhibited negative results in influenza virus propagation at a concentration of 25 µg/mL. Additionally, molecular docking study revealed that 13b–d and 14c bound in 430-cavity of neuraminidase from H5N2 avian influenza virus and the synthesized derivatives also strongly interacted with the key amino acid residues, including Arg371, Pro326, Ile427, and Thr439