M.W=400-450 | Page 2 of 2 | Heterocyclic Building Blocks-piperazine

Hansen-Petrik, Melissa B.’s team published research in Cancer Letters (Shannon, Ireland) in 175 | CAS: 218136-59-5

Cancer Letters (Shannon, Ireland) published new progress about 218136-59-5. 218136-59-5 belongs to piperazines, auxiliary class Metabolic Enzyme,D6D, name is 2,2-Diphenyl-5-(4-((pyridin-3-ylmethylene)amino)piperazin-1-yl)pentanenitrile, and the molecular formula is C27H29N5, Computed Properties of 218136-59-5.

Hansen-Petrik, Melissa B. published the artcileSelective inhibition of Δ-6 desaturase impedes intestinal tumorigenesis, Computed Properties of 218136-59-5, the publication is Cancer Letters (Shannon, Ireland) (2002), 175(2), 157-163, database is CAplus and MEDLINE.

Arachidonic acid is an important polyunsaturated fatty acid involved in cell signaling. It is derived primarily from dietary linoleic acid, and the rate-limiting step in its biosynthesis is the initial desaturation of linoleic acid via Δ-6 desaturase. Evidence suggests that downstream metabolic products of arachidonic acid, e.g. prostaglandins, are involved in colorectal cancer, but involvement of the biosynthetic pathway of arachidonic acid has not been previously investigated. In the present study, the authors report the effects of a novel selective Δ-6 desaturase inhibitor, SC-26196, on tumorigenesis in two in vivo models of intestinal cancer. SC-26196 treatment resulted in 36-37% fewer tumors in Apc^Min/+ mice and 35% decrease in primary tumor size in nude mice bearing HT-29 human colon cancer cell xenografts. As expected, SC-26196 treatment resulted in significantly higher linoleic acid levels in tissue phospholipids and lower levels of arachidonic acid. The effects on both tissue fatty acid composition and tumorigenesis in Apc^Min/+ mice were abrogated by concomitant treatment with dietary arachidonic acid, indicating that the observed effects were due to interference with the biosynthetic pathway of arachidonic acid.

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics

Harmon, Shawn D.’s team published research in Lipids in 38 | CAS: 218136-59-5

Lipids published new progress about 218136-59-5. 218136-59-5 belongs to piperazines, auxiliary class Metabolic Enzyme,D6D, name is 2,2-Diphenyl-5-(4-((pyridin-3-ylmethylene)amino)piperazin-1-yl)pentanenitrile, and the molecular formula is C27H29N5, Related Products of piperazines.

Harmon, Shawn D. published the artcileEffect of the Δ⁶-desaturase inhibitor SC-26196 on PUFA metabolism in human cells, Related Products of piperazines, the publication is Lipids (2003), 38(4), 469-476, database is CAplus and MEDLINE.

The objective of this study was to determine the effect of 2,2-diphenyl-5-(4-{[(1E)-pyridin-3-yl-methylidene]-amino}piperazin-1-yl)pentanenitrile (SC-26196), a Δ⁶-desaturase inhibitor, on PUFA metabolism in human cells. SC-26196 inhibited the desaturation of 2 μM [1-¹⁴C]18:2n-6 by 87-95% in cultured human skin fibroblasts, coronary artery smooth muscle cells, and astrocytes. By contrast, SC-26196 did not affect the conversion of [1-¹⁴C]20:3n-6 to 20:4 in the fibroblasts, demonstrating that it is selective for Δ⁶-desaturase. The IC₅₀ values for inhibition of the desaturation of 2 μM [1-¹⁴C]18:3n-3 and [3-¹⁴C]24:5n-3 in the fibroblasts, 0.2-0.4 μM, were similar to those for the inhibition of [1-¹⁴C]18:2n-6 desaturation, and the rates of recovery of [1-¹⁴C]18:2n-6 and [3-¹⁴C]24:5n-3 desaturation after removal of SC-26196 from the culture medium also were similar. SC-26196 reduced the conversion of [3-¹⁴C]22:5n-3 and [3-¹⁴C]24:5n-3 to DHA by 75 and 84%, resp., but it had no effect on the retroconversion of [3-¹⁴C]24:6n-3 to DHA. These results demonstrate that SC-26196 effectively inhibits the desaturation of 18- and 24-carbon PUFA and, therefore, decreases the synthesis of arachidonic acid, EPA, and DHA in human cells. Furthermore, they provide addnl. evidence that the conversion of 22:5n-3 to DHA involves Δ⁶-desaturation

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics

Spencer, John’s team published research in ACS Combinatorial Science in 13 | CAS: 1012785-48-6

ACS Combinatorial Science published new progress about 1012785-48-6. 1012785-48-6 belongs to piperazines, auxiliary class Boronic acid and ester, name is tert-Butyl 4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperazine-1-carboxylate, and the molecular formula is C3H5F3O, Product Details of C22H35BN2O4.

Spencer, John published the artcileMicrowave-mediated synthesis of an arylboronate library, Product Details of C22H35BN2O4, the publication is ACS Combinatorial Science (2011), 13(1), 24-31, database is CAplus and MEDLINE.

A series of arylboronates has been synthesized from the reaction of 2-(2-, (3-, or (4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane resp. with a range of N-, S-, and O-nucleophiles, using microwave-mediated chem. For the synthesis of N- and S-substituted boronates, a supported base, PS-NMM, was employed, and many reactions were complete within 15 min. With O-nucleophiles, a mixture of tetrabutylammonium bromide, potassium carbonate, and sodium hydroxide was employed. The resulting aminomethyl, mercaptomethyl, or alkoxy-/phenoxymethyl-arylboronates were subjected to microwave-mediated Suzuki Miyaura coupling reactions to afford a range of biaryls in moderate to good yields. The x-ray structures of five boronates were determined

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics

Young, Reuben S. E.’s team published research in Cell Reports in 34 | CAS: 218136-59-5

Cell Reports published new progress about 218136-59-5. 218136-59-5 belongs to piperazines, auxiliary class Metabolic Enzyme,D6D, name is 2,2-Diphenyl-5-(4-((pyridin-3-ylmethylene)amino)piperazin-1-yl)pentanenitrile, and the molecular formula is C11H10N4, Name: 2,2-Diphenyl-5-(4-((pyridin-3-ylmethylene)amino)piperazin-1-yl)pentanenitrile.

Young, Reuben S. E. published the artcileApocryphal FADS2 activity promotes fatty acid diversification in cancer, Name: 2,2-Diphenyl-5-(4-((pyridin-3-ylmethylene)amino)piperazin-1-yl)pentanenitrile, the publication is Cell Reports (2021), 34(6), 108738, database is CAplus and MEDLINE.

Canonical fatty acid metabolism describes specific enzyme-substrate interactions that result in products with well-defined chain lengths, degree(s), and positions of unsaturation Deep profiling of lipids across a range of prostate cancer cell lines reveals a variety of fatty acids with unusual site(s) of unsaturation that are not described by canonical pathways. The structure and abundance of these unusual lipids correlate with changes in desaturase expression and are strong indicators of cellular phenotype. Gene silencing and stable isotope tracing demonstrate that direct Δ6 and Δ8 desaturation of 14:0 (myristic), 16:0 (palmitic), and 18:0 (stearic) acids by FADS2 generate new families of unsaturated fatty acids (including n-8, n-10, and n-12) that have rarely-if ever-been reported in human-derived cells. Isomer-resolved lipidomics reveals the selective incorporation of these unusual fatty acids into complex structural lipids and identifies their presence in cancer tissues, indicating functional roles in membrane structure and signaling.

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics