7,8,9,9-Tetradehydroisolariciresinol

Higher Expression of Toll-like Receptors 3, 7, 8, and 9 in Pityriasis Rosea.[Pubmed:28192646]

J Pathol Transl Med. 2017 Mar;51(2):148-151.

BACKGROUND: Pityriasis rosea (PR) is a common papulosquamous skin disease in which an infective agent may be implicated. Toll-like receptors (TLRs) play an important role in immune responses and in the pathophysiology of inflammatory skin diseases. Our aim was to determine the possible roles of TLRs 3, 7, 8, and 9 in the pathogenesis of PR. METHODS: Twenty-four PR patients and 24 healthy individuals (as controls) were included in this case control study. All recruits were subjected to routine laboratory investigations. Biopsies were obtained from one active PR lesion and from healthy skin of controls for the detection of TLR 3, 7, 8, and 9 gene expression using real-time polymerase chain reaction. RESULTS: This study included 24 patients (8 females and 16 males) with active PR lesions, with a mean age of 28.62 years. Twenty four healthy age- and sex-matched individuals were included as controls (8 females and 16 males, with a mean age of 30.83 years). The results of the routine laboratory tests revealed no significant differences between both groups. Significantly elevated expression of all studied TLRs were detected in PR patients relative to healthy controls (p < .001). CONCLUSIONS: TLRs 3, 7, 8, and 9 might be involved in the pathogenesis of PR.

A Unified Approach to the Isomeric alpha-, beta-, gamma-, and delta-Carbolines via their 6,7,8,9-Tetrahydro Counterparts.[Pubmed:28304164]

J Org Chem. 2017 Apr 21;82(8):4328-4335.

A cross-coupling/reductive cyclization protocol has been employed in a unified approach to all four carbolines. So, for example, the 2-nitropyridine 8, which is readily prepared through an efficient palladium-catalyzed Ullmann cross-coupling reaction, is reductively cyclized under conventional conditions to give 6,7,8,9-tetrahydro-alpha-carboline that is itself readily aromatized to give alpha-carboline (1).

Pharmacological evaluation of 9,10-dihydrochromeno[8,7-e][1,3]oxazin-2(8H)-one derivatives as potent anti-inflammatory agent.[Pubmed:28273501]

Pharmacol Rep. 2017 Jun;69(3):419-425.

BACKGROUND: Non-steroidal anti-inflammatory drugs (NSAIDs) are the most widely administered drugs for the treatment of inflammation. However, they usually cause some unexpected side effects. Coumarins and their derivatives exhibit broad-spectrum biological activities. In order to develop new anti-inflammatory drugs with high anti-inflammatory activity and less side effects, a series of 9-substituted-9,10-dihydrochromeno[8,7-e][1,3]oxazin-2(8H)-one derivatives were designed, synthesized, and screened for their anti-inflammatory activities. METHODS: We investigated the effect of compound 9-(2-chlorophenyl)-9,10-dihydrochromeno[8,7-e][1,3]oxazin-2(8H)-one (B3) on lipopolysaccharide (LPS)-induced cytokine levels in RAW 264.7 cells at concentrations between 6.25mug/ml and 25mug/ml. Concentrations of tumor necrosis factor-alpha (TNF-alpha) and interleukin-6 (IL-6) were measured by enzyme-linked immunosorbent assay (ELISA). Moreover, mitogen-activated protein kinase (MAPK) and nuclear factor-kappaB (NF-kappaB) activation was investigated by western blot assay. RESULTS: Compound B3 could inhibit inflammatory responses via suppression of the NF-kappaB and MAPK signaling pathways. Docking study of the prepared compounds was performed for the study of interaction of molecules with the active site of TNF-alpha. CONCLUSION: 9,10-Dihydrochromeno[8,7-e][1,3]oxazin-2(8H)-one derivatives showed anti-inflammatory activity. Compound B3 was the most potent. The results of this study are encouraging further investigations to develop compound B3 as a novel therapeutic agent for inflammatory disorders.

Crystal structure of 9,20-dimethyl-1,8,12,19-tetra-aza-tetra-cyclo-[17.3.1.0(2,7).0(13,18)]tricosane dihydrate from synchrotron X-ray data.[Pubmed:28316816]

Acta Crystallogr E Crystallogr Commun. 2017 Feb 17;73(Pt 3):387-389.

The structure of the title compound, C21H40N4.2H2O, has been determined from synchrotron X-ray radiation data. The asymmetric unit comprises one 12-membered macropolycycle and two lattice water mol-ecules. The macropolycycle contains two cyclo-hexane rings and one 1,3-di-aza-cyclo-hexane ring, all in chair conformations. The C-N and C-C bond lengths are in the ranges 1.4526 (16)-1.4786 (17) and 1.517 (2)-1.5414 (17) A, respectively. One intra-molecular N-Hcdots, three dots, centeredN hydrogen bond helps to stabilize the mol-ecular conformation while medium-strength inter-molecular N-Hcdots, three dots, centeredO, O-Hcdots, three dots, centeredN and O-Hcdots, three dots, centeredO hydrogen bonds involving the lattice water mol-ecules connect the components into a three-dimensional network.