Month: December 2022

Penthala, Narsimha R. published the artcileAntitumor properties of novel sesquiterpene lactone analogs as NFκB inhibitors that bind to the IKKβ ubiquitin-like domain (ULD), SDS of cas: 6850-57-3, the publication is European Journal of Medicinal Chemistry (2021), 113675, database is CAplus and MEDLINE.

Melampomagnolide B (MMB) is a parthenolide (PTL) based sesquiterpene lactone that has been used as a template for the synthesis of a plethora of lead anticancer agents owing to its reactive C-10 primary hydroxyl group. Such compounds have been shown to inhibit the IKKβ subunit, preventing phosphorylation of the cytoplasmic IκB inhibitory complex. The present study focuses on the synthesis and in vitro antitumor properties of novel benzyl and phenethyl carbamates of MMB. Screening of these MMB carbamates identified analogs with potent growth inhibition properties against a panel of 60 human cancer cell lines (71% of the mols. screened had GI₅₀ values < 2μM). Two analogs, the 4-methoxybenzyl carbamate (I) and the 4-bromophenethyl carbamate, were the most active compounds Lead compound I inhibited cell proliferation in M9 ENL AML cells, and in TMD-231, OV-MD-231 and SUM149 breast cancer cell lines. Interestingly, mechanistic studies showed that I did not inhibit p65 phosphorylation in M9 ENL AML and OV-MD-231 cells, but did inhibit phosphorylation of both p65 and IκBα in SUM149 cells. 4-Methoxybenzyl carbamate also reduced NFκB binding to DNA in both OV-MD-231 and SUM149 cells. Mol. docking studies indicated that I and the 4-bromophenethyl carbamate are both predicted to interact with the ubiquitin-like domain (ULD) of the IKKβ subunit. These data suggest that in SUM149 cells, I is likely acting as an allosteric inhibitor of IKKβ, whereas in M9 ENL AML and OV-MD-231 cells. 4-Methoxybenzyl carbamate is able to inhibit an event after IκB/p65/p50 phosphorylation by IKKβ that leads to inhibition of NFκB activation and reduction in NFκB-DNA binding. The 4-methoxybenzyl carbamate analog I was by far the most potent compound in either carbamate series, and was considered an important lead compound for further optimization and development as an anticancer agent.

European Journal of Medicinal Chemistry published new progress about 6850-57-3. 6850-57-3 belongs to ethers-buliding-blocks, auxiliary class Amine,Benzene,Ether, name is (2-Methoxyphenyl)methanamine, and the molecular formula is C8H11NO, SDS of cas: 6850-57-3.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Leitch, Leonard C. published the artcileSynthesis of sulfanilylthiourea and related compounds, Safety of Formamidine disulfide dihydrochloride, the publication is Canadian Journal of Research, Section B: Chemical Sciences (1945), 139-57, database is CAplus.

Sulfanilylthiourea (I) was prepared for investigation of its chemotherapeutic properties (1) by reaction of acetylsulfanilylcyanamide (II) with H₂S or (NH₄)₂S (III) followed by deacetylation, and (2) from III and sulfanilylcyanamide (IV). A review of previous preparations of I is given. To a solution of Ca cyanamide (V) (220 g.) in H₂O (1300 mL.), stirred 3 h. at room temperature, was added p-AcNHC₆H₄SO₂Cl (VI) (200 g.) in portions for over 50 min. at 25-30°. After stirring 2 h. longer, the solution was brought to a boil, filtered, and CaCl₂.2H₂O (220 g.) dissolved in the filtrate. On cooling and standing 79% (176 g.) of Ca acetylsulfanilylcyanamide (VII) was obtained. Deacetylation of VII gave 90% of IV, m. 292-5° (decomposition). VII heated to 100° with 6 N HCl, cooled, and neutralized with NH₄OH gave sulfanilylurea (VIII) as a gum which on purification gave VIII hydrate (IX), m. 121-4°; VIII, obtained by heating IX at 100°, m. 143-7°. VII (13 g.) heated 15 h. at 95-100° with 20% III solution (33 mL.) gave 70.5% crude acetylsulfanilylthiourea (X) which after purification m. 197.5-8° (decomposition). At 160° III and VII gave acetylsulfanilamide. X (0.1 mol) added to NaOH (0.1 mol) in H₂O (200 mL.), warmed until solution was complete, decolorized, and treated with NaCl (30 g.), gave Na acetylsulfanilylthiourea (XI), m. 234.5-5°. XI (0.1 mol), 1,2-dichloroethyl acetate (0.1 mol), NaOAc.3H₂O (0.12 mol), and H₂O (100 mL.) heated to 90° for 1 h. and cooled gave 79% of acetylsulfathiazole (XII), m. 258-60°. Deacetylation of XII with NaOH gave 74.5% of sulfathiazole, m. 198-200°. IV (0.101 mol) and 20% III solution (50 mL.) heated 1 h. at 160°, cooled, and adjusted to pH 3.5 gave 89.5% of I, m. 171.5-2° (decomposition). Deacetylation of X to I was effected with 10% NaOH or 7% HCl. VII reacted with aniline gave 1-(N⁴-acetylsulfanilyl)-3-phenylguanidine, m. 221-4° (from HOAc), which on deacetylation gave 1-sulfanilyl-3-phenylguanidine; m. 206-7° (from 75% EtOH). VII with p-nitroaniline gave 1-(N⁴-acetylsulfanilyl)-3-(4-nitrophenyl)guanidine (XIII), m. 254-5°, which on deacetylation gave 1-sulfanilyl-3-(4-nitrophenyl)guanidine, m. 235-6°. XIII reduced with Fe powder and dilute HOAc and deacetylated gave 1-sulfanilyl-3-(4-aminophenyl)guanidine, m. 200-1°. Anthranilic acid and VII gave 1-(N⁴-acetylsulfanilyl)-3-(2-carboxyphenyl)guanidine (XIV), m. 286-8°, which on deacetylation gave 1-sulfanilyl-3-(2-carboxyphenyl)guanidine, m. 265-6°. XIV Na salt m. above 300°. VII, reacted with NH₄Cl at 154° for 4 h., gave acetylsulfaguanidine (XV), m. 260-2°. XV and sulfaguanidine (XVI) (from the deacetylation of XV) form a crystalline product, probably a mol. complex, m. 98-150°. XVI, m. 187°, was also prepared from IV and concentrated NH₄OH at 165°. To thiourea (0.125 mol) in Me₂CO (200 mL.) was added VI (0.124 mol) after which the mixture was stirred under reflux for 1 h. Filtration gave solid dithiodiformamidine-2HCl, m. 173-5°, while from the filtrate p-acetamidophenyl p-acetamidobenzenethiosulfonate (AcNHC₆H₄SO₂SC₆H₄NHAc) (XVII), m. 225-7° (decomposition), crystallized Deacetylation of XVII with 20% EtOH-HCl gave p-aminophenyl p-aminobenzenethiosulfonate-HCl, m. 176-9° (decomposition). 2-Methyl-2-thiopseudourea coupled with VI gave 76% of 3-(N⁴-acetylsulfanilyl)-2-methyl-2-thiopseudourea (XVIII), m. 234-5°. XVIII heated with dilute HCl, was deacetylated to 3-sulfanilyl-2-methyl-2-thiopseudourea, m. 182-4°. 2-Benzyl-2-thiopseudourea-HCl, reacted with VI gave 96.5% of 3-(N⁴-acetylsulfanilyl)-2-benzyl-2-thiopseudourea, m. 168-9°, which was deacetylated with EtOH-HCl to 3-sulfanilyl-2-benzyl-2-thiopseudourea, m. 144.5-5.5°. Thiourea (0.25 mol) refluxed 30 min. in ethanol (150 mL.) with ethylene bromide (0.25 mol) gave 72.3% of 1,2-bis(2-thiopseudourea hydrobromide) ethane (XIX), m. 238-40°, instead of the expected 2-(2-bromoethyl)-2-thiopseudourea hydrobromide. XIX reacted with VI gave 3-(N⁴-acetylsulfanilyl)-2-(2-hydroxyethyl)-2-thiopseudourea, m. 236-8°, which was deacetylated with EtOH-HCl to 3-sulfanilyl-2-(2-hydroxyethyl)-2-thiopseudourea, m. 171-3°. Acyl pseudothioureas coupled with VI gave only XVII.

Canadian Journal of Research, Section B: Chemical Sciences published new progress about 14807-75-1. 14807-75-1 belongs to ethers-buliding-blocks, auxiliary class Salt,Thiourea,Amine,Aliphatic hydrocarbon chain, name is Formamidine disulfide dihydrochloride, and the molecular formula is C2H8Cl2N4S2, Safety of Formamidine disulfide dihydrochloride.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Annunziatini, Claudia published the artcileAryl substituted N-hydroxyphthalimides as mediators in the laccase-catalyzed oxidation of lignin model compounds and delignification of wood pulp, Product Details of C16H18O4, the publication is Journal of Molecular Catalysis B: Enzymatic (2005), 32(3), 89-96, database is CAplus.

Aryl substituted N-hydroxyphthalimides (NHPIs) have been tested as mediators in the laccase-promoted oxidation of non-phenolic monomeric and dimeric lignin model compounds and in the delignification of kraft pulp samples. In the oxidation of the model compounds a significant increase in the product yields was observed upon increasing the electron donating properties of the NHPI ring substituent. Product yields also increased, but to a smaller extent, by increasing the electron donating properties of the aromatic substituent in the lignin models. These results suggest the contribution to the overall reactivity of both the oxidation of the aryl substituted NHPI to the N-oxyl radical (X-PINO) by laccase and the hydrogen atom transfer step from the substrate to the X-PINO, with a major contribution of the former process. When applied to the delignification of kraft pulps again the mediation efficiency increased by increasing the electron donating properties of the NHPI aryl substituent, the best mediators being 4-Me-NHPI and 4-MeO-NHPI. Thus, the use of non-phenolic lignin model compounds in the oxidation promoted by the laccase/X-NHPI system is well suited to mimic the behavior of the lignin polymer.

Journal of Molecular Catalysis B: Enzymatic published new progress about 183303-74-4. 183303-74-4 belongs to ethers-buliding-blocks, auxiliary class Benzene,Alcohol,Ether, name is 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol, and the molecular formula is C16H18O4, Product Details of C16H18O4.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Micewicz, Ewa D. published the artcileSmall lipidated anti-obesity compounds derived from neuromedin U, Application of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is European Journal of Medicinal Chemistry (2015), 616-626, database is CAplus and MEDLINE.

A small library of truncated/lipid-conjugated neuromedin U (NmU) analogs was synthesized and tested in vitro using an intracellular calcium signaling assay. The selected, most active analogs were then tested in vivo, and showed potent anorexigenic effects in a diet-induced obese (DIO) mouse model. The most promising compound, NM4-C₁₆ was effective in a once-weekly-dose regimen. Collectively, the authors’ findings suggest that short, lipidated analogs of NmU are suitable leads for the development of novel anti-obesity therapeutics.

European Journal of Medicinal Chemistry published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, Application of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Anderson, Nichole published the artcileProcedure for the rapid synthesis of the monomer 1,4-bis(chloromethyl)-2-(2-ethylhexyloxy)-5-methoxybenzene, Category: ethers-buliding-blocks, the publication is Synthetic Communications (2008), 38(22), 3903-3908, database is CAplus.

The alkylation of 4-methoxyphenol with 2-ethylhexyl bromide was accelerated by using potassium tert-butoxide in DMF. Subsequent chloromethylation occurred quickly using acetic acid as a cosolvent to give the monomer (for MEH-PPV) in 61% overall yield on a 2-mol scale.

Synthetic Communications published new progress about 146370-51-6. 146370-51-6 belongs to ethers-buliding-blocks, auxiliary class Benzene,Ether, name is 1-((2-Ethylhexyl)oxy)-4-methoxybenzene, and the molecular formula is C15H24O2, Category: ethers-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Vincent, Andrea published the artcileIdentification of candidate drugs for the treatment of ALS, Related Products of ethers-buliding-blocks, the publication is Amyotrophic Lateral Sclerosis and Other Motor Neuron Disorders (2005), 6(1), 29-36, database is CAplus and MEDLINE.

A consortium of investigators interested in neurodegenerative diseases collaborated to screen 1040 drugs in multiple neurodegenerative disease assays. One model of amyotrophic lateral sclerosis (ALS) pathogenesis in particular incorporated glutamate exposure in enriched primary rat motor neuron cultures. In this model 78 compounds decreased motor neuron death caused by 100 μM glutamate. Almost all these pharmacol. agents act at one or more of the following cellular targets: (1) protein synthesis inhibition; (2) Cox inhibition; (3) regulation of anion flux; (4) modulation of GABA receptors; (5) antioxidant, and (6) cell cycle inhibition. The most prevalent mode of action was the regulation of intracellular calcium. These data extend the understanding of motor neuron degeneration and identify a number of cellular targets for the improvement of combined therapies for neurodegenerative disease.

Amyotrophic Lateral Sclerosis and Other Motor Neuron Disorders published new progress about 637-58-1. 637-58-1 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride, and the molecular formula is C42H63O3P, Related Products of ethers-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Lemarchand, Aude published the artcileSynthesis of chiral ansa-bridged macrocyclic lactams ([16]metacyclophanes) related to geldanamycin, Computed Properties of 99438-28-5, the publication is Synthesis (2005), 1977-1990, database is CAplus.

Two chiral ansa-bridged lactams ([16]metacyclophanes) I (X = CH₂, O) were synthesized starting from 2-methoxyhydroquinone diisopropyl ether in 14 (I, X = CH₂, 3.9% overall) and 16 synthetic steps (I X = O, 0.6% overall). Both compounds contain typical features of geldanamycin in the C-1 to C-9 part of the ansa chain, i.e. the α,β,γ,δ-unsaturated anilide (C-1 to C-5), the carbamate at the stereogenic carbon atom C-7 and the E-double bond between C-8 and C-9. While the rest of the ansa chain (C-10 to C-15) was an alkyl chain in compound I (X = CH₂), a more polar CH₂OCH₂CH₂OCH₂ chain was installed in compound I (X = O). Key step of the sequence was a ring-closing metathesis in which the ansa compounds were formed as a mixture of isomers. Deprotection and oxidation to the quinone failed for diisopropyl ether I (X = O) but was successfully conducted with precursor I (X = CH₂).

Synthesis published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Computed Properties of 99438-28-5.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Hanessian, Stephen published the artcileAlternative and Expedient Asymmetric Syntheses of L-(+)-Noviose, Synthetic Route of 99438-28-5, the publication is Organic Letters (2008), 10(2), 261-264, database is CAplus and MEDLINE.

L-(+)-Noviose I, the sugar component of the antibiotic novobiocin, was synthesized from either 2,2-dimethyl-1,3-cyclopentadione or benzyl glyoxylate relying on stoichiometric and asym. processes by two independent methods, comprising six and nine steps, in 27 and 20% overall yields, resp. An unsaturated lactone II was prepared via stereoselective boron-catalyzed reduction, scandium-catalyzed Baeyer-Villiger oxidation and Saegusa oxidation from 2,2-dimethyl-1,3-cyclopentadione. II could also be prepared via stereoselective Brown allylation, ruthenium-catalyzed isomerization and ring-closing metathesis, and allylic oxidation from benzyl glyoxylate. II was then transformed to I via stereoselective reduction and dihydroxylation.

Organic Letters published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Synthetic Route of 99438-28-5.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Organ, Michael G. published the artcilePd-PEPPSI-IHept^Cl: A General Purpose, Highly Reactive Catalyst for the Selective Coupling of Secondary Alkyl Organozincs, Synthetic Route of 2944-47-0, the publication is Chemistry – A European Journal (2016), 22(41), 14531-14534, database is CAplus and MEDLINE.

Pd-PEPPSI-IHept^Cl, a new, very bulky yet flexible Pd-NHC complex was evaluated in the Negishi coupling of secondary alkylzinc reactants with a wide variety of oxidative addition partners in high yields and excellent selectivity. The desired, direct reductive elimination branched products I [Ar = 2-pyridyl, 5-indolyl, 3-benzo[b]thiophenyl, etc.], II and e.g., III, were obtained with no sign of migratory insertion across electron-rich and electron poor aromatics and all forms of heteroaromatics (5- and 6-membered). Impressively, there was no impact of substituents at the site of reductive elimination (i.e., ortho or even di-ortho), which was not yet been demonstrated by another catalyst system to date.

Chemistry – A European Journal published new progress about 2944-47-0. 2944-47-0 belongs to ethers-buliding-blocks, auxiliary class Benzene,Ether, name is 2-Isopropylanisole, and the molecular formula is C10H14O, Synthetic Route of 2944-47-0.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Geduk, Aysun Sener published the artcileLC-MS/MS phenolic composition of peach (Prunus persica L. Batsch) extracts and an evaluation of their antidiabetic, antioxidant, and antibacterial activities, Related Products of ethers-buliding-blocks, the publication is South African Journal of Botany (2022), 636-645, database is CAplus.

Peaches contain high amounts of polyphenol compounds The consumption of peaches gives protection against various conditions such as obesity, diabetes, cardiovascular and bacterial diseases, and inflammation. The present study aimed to examine the phytochem. compounds and the antioxidant, antibacterial, anti-α-glucosidase, and anti-α-amylase activities of the different extracts (methanol, ethanol, and hexane) of fresh red peach collected from the Mersin province in Turkey. In this study, chem. compositions of methanol and ethanol extracts prepared from peach pulp were studied by using liquid chromatog.-mass spectrometry (LC-MS/MS). Thirteen metabolites: quinic acid, fumaric acid, aconitic acid, protocatechuic acid, salicylic acid, chlorogenic acid, rutin, isoquercitrin, hesperidin, astragalin, nicotiflorin, quercetin, and amentoflavone, were identified in ethanol extracts and also these phenolic compounds, excluding salicylic acid, were identified in the methanol extract The ethanol extract showed the most activity in all enzyme inhibition and in antibacterial and antioxidative activity assays, which is mainly due to its rich phenolic content. The most dominant compounds determined in ethanol extract were quinic acid, chlorogenic acid, fumaric acid, and isoquercitrin resp. According to the results of this study, ethanol extract in particular is a potential ingredient to be used in food-derived antidiabetic and antibacterial formulations.

South African Journal of Botany published new progress about 134-96-3. 134-96-3 belongs to ethers-buliding-blocks, auxiliary class Immunology/Inflammation,COX,Natural product, name is 4-Hydroxy-3,5-dimethoxybenzaldehyde, and the molecular formula is C9H10O4, Related Products of ethers-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem