Month: December 2022

Kadu, Vikas D. published the artcileRapid One-Pot Aerobic Oxidative N-α-C(sp³)-H Functionalization of Arylmethylamines to Access Tetrasubstituted Imidazoles, Recommanded Product: (2-Methoxyphenyl)methanamine, the publication is Asian Journal of Organic Chemistry (2022), 11(8), e202200162, database is CAplus.

A simple copper catalyzed “one-pot” process has been developed for synthesis of polysubstituted imidazoles via direct oxidative N-α-C(sp³)-H functionalization of arylmethylamines. The readily available arylmethylamines as substrates have afforded tetrasubstituted imidazoles products up to 94% yields under mild and environmentally benign conditions. The explored substrates scope with 1,2-diketones and α-hydroxyketones have shown great utility for synthesis of tetrasubstituted imidazoles.

Asian Journal of Organic 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, Recommanded Product: (2-Methoxyphenyl)methanamine.

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

Jacobs, Emily published the artcileExperimental and Computational Studies towards Chemoselective C-F over C-Cl Functionalisation: Reversible Oxidative Addition is the Key, COA of Formula: C11H10O, the publication is ChemCatChem (2021), 13(2), 637-645, database is CAplus.

Catalytic cross-coupling is a valuable tool for forming new carbon-carbon and carbon-heteroatom bonds, allowing access to a variety of structurally diverse compounds However, for this methodol. to reach its full potential, precise control over all competing cross-coupling sites in poly-functionalized building blocks is required. Carbon-fluorine bonds are one of the most stable bonds in organic chem., with oxidative addition at C-F being much more difficult than at other C-halide bonds. As such, the development of methods to chemoselectively functionalize the C-F position in poly-halogenated arenes would be very challenging if selectivity was to be induced at the oxidative addition step. However, metal-halide complexes exhibit different trends in reactivity to the parent haloarenes, with metal-fluoride complexes known to be very reactive towards transmetalation. In this current work, we sought to exploit the divergent reactivity of Ni-Cl and Ni-F intermediates to develop a chemoselective C-F functionalization protocol, where selectivity is controlled by the transmetalation step. Our exptl. studies highlight that such an approach is feasible, with a number of nickel catalysts shown to facilitate Hiyama cross-coupling of 1-fluoronaphthalene under base-free conditions, while no cross-coupling with 1-chloronaphthalene occurred. Computational and exptl. studies revealed the importance of reversible C-Cl oxidative addition for the development of selective C-F functionalization, with ligand effects on the potential for reversibility also presented.

ChemCatChem published new progress about 93-04-9. 93-04-9 belongs to ethers-buliding-blocks, auxiliary class Naphthalene,Ether, name is 2-Methoxynaphthalene, and the molecular formula is C11H10O, COA of Formula: C11H10O.

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

Kaneda, Masato published the artcileStructure-Activity Relationship Study on Odoamide: Insights into the Bioactivities of Aurilide-Family Hybrid Peptide-Polyketides, Application of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is ACS Medicinal Chemistry Letters (2018), 9(4), 365-369, database is CAplus and MEDLINE.

Odoamide is a cytotoxic peptide-polyketide hybrid mol. isolated from the Okinawan marine cyanobacterium Okeania sp. For an efficient structure-activity relationship study of the peptide part of odoamide, a facile synthetic protocol was established using a solid-phase peptide synthesis. Among a series of peptides, the D-MeAla6 isomer exhibited a more potent cytotoxicity than natural odoamide. It was also demonstrated that the 26-membered macrocyclic natural odoamide I and the 24-membered isomer with comparable cytotoxicities were slowly interconvertible, and both isomers contributed to the potent cytotoxicity of odoamide. Examination of the physicochem. properties revealed that the in vitro cytotoxicity was affected by the serum protein binding of odoamide derivatives, while the differences in the macrocyclic structures had no significant effect on the membrane permeability.

ACS Medicinal Chemistry Letters 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

Hattori, Hiromu published the artcileTotal Synthesis of Tiacumicin A. Total Synthesis, Relay Synthesis, and Degradation Studies of Fidaxomicin (Tiacumicin B, Lipiarmycin A3), Related Products of ethers-buliding-blocks, the publication is Journal of Organic Chemistry (2018), 83(13), 7180-7205, database is CAplus and MEDLINE.

The com. macrolide antibiotic fidaxomicin was synthesized in a highly convergent manner. Salient features of this synthesis include a β-selective noviosylation, a β-selective rhamnosylation, a ring closing metathesis, a Suzuki coupling and a vinylogous Mukaiyama aldol reaction. Careful choice of protecting groups and fine tuning of the glycosylation reactions led to the first total synthesis of fidaxomicin. In addition, a relay synthesis of fidaxomicin was established, which gives access to a conveniently protected intermediate from the natural material for derivatization. The first total synthesis of a related congener, tiacumicin A, is presented.

Journal of Organic Chemistry 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, Related Products of ethers-buliding-blocks.

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

Thoma, K. published the artcileColloid association and bioavailability of local anesthetics. Part 7. Partition behavior, Safety of 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride, the publication is Pharmaceutica Acta Helvetiae (1988), 63(6), 155-9, database is CAplus and MEDLINE.

The partition coefficient was determined for 20 local anesthetics and was found to be considerably influenced by the chem. structure and the substituents present in the compounds In the system n-octanol/buffer (pH 5.7) partition coefficients between 0.05 (brufacaine-HCl) and 199.0 (chinisocaine-HCl) were found. In the system n-octanol/water they ranged between 0.003 (procaine-HCl and lidocaine-HCl) and 4.2 (oxetacaine-HCl). Raising the pH-value from 4 to 6 resulted in an increase of the partition coefficient of stadacain-HCl from 8.9 to 56.5. Raising the ionic strength from 0.2 to 1.0 of a pH 5.7 buffer increased the partition coefficient of stadacain-HCl from 30.4 to 95.3%. The addition of 5.0% NaCl to an aqueous, unbuffered solution of stadacain-HCl increased the partition coefficient from 0.36 to 27.2.

Pharmaceutica Acta Helvetiae 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 C5H5BrN2, Safety of 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride.

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

Thoma, K. published the artcileColloid association and bioavailability of local anesthetics. Part 6. Mixed micelle formation with polysorbates, Product Details of C17H28ClNO3, the publication is Pharmaceutica Acta Helvetiae (1988), 63(4-5), 102-10, database is CAplus and MEDLINE.

For 19 surface-active local anesthetics, the binding to polyethylene glycol sorbitan fatty acid esters (I) by formation of mixed micelles was determined All surface-active local anesthetics investigated, except procaine-HCl and lidocaine-HCl, form mixed micelles with I. In the presence of 5% I in water, this binding fluctuates between 5.3% for butacaine sulfate and 75% for cyclomethycaine-sulfate. For all local anesthetics the quotient of the total concentration and the free moiety is proportional to the surfactant concentration The surfactant bound moiety of the local anesthetic is constant when it is below its critical micellar concentration (CMC). Above the CMC, deviations from this rule are observed The binding of tetracaine-HCl to I by mixed micelles formation demonstrates that the binding to these surfactants increases with the shortened fatty acid chain (that means an increasing HLB-value). When the pH-value or ionic strength increases, stadacain-HCl exhibits a distinct increase of the binding by a change of the dissociation-rate or a salting-out effect. Changing the solvent of stadacain-HCl from water to saline, for example, increases the binding to 5% I from 38.1 to 68%.

Pharmaceutica Acta Helvetiae 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 C19H14N2, Product Details of C17H28ClNO3.

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

Hirose, Tomoyasu published the artcileSolution-phase total synthesis of the hydrophilic natural product argifin using 3,4,5-tris(octadecyloxy)benzyl tag, Product Details of C25H23NO4, the publication is Tetrahedron (2011), 67(35), 6633-6643, database is CAplus.

A solution-phase total synthesis of argifin using 3,4,5-tris(octadecyloxy)benzyl tag as a hydrophobic protective group of carboxylic acid was developed to produce 44% overall yield for 16 linear steps. Argifin, a novel class of natural product chitinase inhibitor, is a highly water-soluble cyclic pentapeptide, so hitherto, only solid-phase synthesis techniques have been used to conveniently prepare the compound and its derivatives 3,4,5-Tris(octadecyloxy)benzyl alc. (HO-TAGa) and its esters are highly crystalline materials and highly capable of dissolving in less-polar solvents such as dichloromethane, benzene, THF, etc., but insoluble in polar solvents such as methanol and DMSO. The combination of HO-TAGa and Fmoc-based peptide synthesis, together with simple purification by recrystallization from MeOH solution, furnished an efficient and practical route of argifin production in the liquid-phase.

Tetrahedron 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, Product Details of C25H23NO4.

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

Aleyasin, Hossein published the artcileAntihelminthic Benzimidazoles Are Novel HIF Activators That Prevent Oxidative Neuronal Death via Binding to Tubulin, Safety of 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride, the publication is Antioxidants & Redox Signaling (2015), 22(2), 121-134, database is CAplus and MEDLINE.

Aims: Pharmacol. activation of the adaptive response to hypoxia is a therapeutic strategy of growing interest for neurol. conditions, including stroke, Huntington’s disease, and Parkinson’s disease. We screened a drug library with known safety in humans using a hippocampal neuroblast line expressing a reporter of hypoxia-inducible factor (HIF)-dependent transcription. Results: Our screen identified more than 40 compounds with the ability to induce hypoxia response element-driven luciferase activity as well or better than deferoxamine, a canonical activator of hypoxic adaptation. Among the chem. entities identified, the antihelminthic benzimidazoles represented one pharmacophore that appeared multiple times in our screen. Secondary assays confirmed that antihelminthics stabilized the transcriptional activator HIF-1α and induced expression of a known HIF target gene, p21^cip1/waf1, in post-mitotic cortical neurons. The on-target effect of these agents in stimulating hypoxic signaling was binding to free tubulin. Moreover, antihelminthic benzimidazoles also abrogated oxidative stress-induced death in vitro, and this on-target effect also involves binding to free tubulin. Innovation and Conclusions: These studies demonstrate that tubulin-binding drugs can activate a component of the hypoxic adaptive response, specifically the stabilization of HIF-1α and its downstream targets. Tubulin-binding drugs, including antihelminthic benzimidazoles, also abrogate oxidative neuronal death in primary neurons. Given their safety in humans and known ability to penetrate into the central nervous system, antihelminthic benzimidazoles may be considered viable candidates for treating diseases associated with oxidative neuronal death, including stroke. Antioxid. Redox Signal. 22, 121-134.

Antioxidants & Redox Signaling 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 C17H28ClNO3, Safety of 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride.

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

Karimi Askarani, Hajar published the artcileOne-pot synthesis of polyhydroquinoline derivatives using nano-Fe₃O₄@dextrin/BF₃ as a magnetic biodegradable catalyst, Formula: C9H10O4, the publication is Journal of the Iranian Chemical Society (2022), 19(7), 3189-3203, database is CAplus.

In this study, the magnetized nano-dextrin-supported boron trifluoride (nano-Fe₃O₄@dextrin/BF₃) as a green biopolymer-based catalyst is synthesized in two steps. In the first step, nano-dextrin is magnetized (nano-Fe₃O₄@dextrin), and in the second step, the BF₃ is supported to the obtained nano-Fe₃O₄@dextrin. The structure of nano-Fe₃O₄@dextrin/BF₃ is characterized by different techniques, including Fourier transform IR (FT-IR) spectroscopy, X-ray diffraction (XRD) pattern, energy dispersive X-ray (EDX) anal., SEM (SEM) imaging, mapping, vibrating sample magnetometer (VSM), and thermogravimetric anal. (TGA/DTG). The catalytic efficiency was also investigated in the synthesis of biol. active polyhydroquinoline derivatives via Hantzsch condensation reaction of aromatic aldehydes, dimedone, Et acetoacetate, and ammonium acetate under solvent-free conditions. The structure of products was confirmed by their m.ps. (MP), FT-IR, and ¹H and ¹³C NMR (NMR) spectroscopy. This procedure enjoys advantages such as short reaction time, clean and fast work-up, and easy separation of the catalyst by an external magnet.

Journal of the Iranian Chemical Society 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, Formula: C9H10O4.

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

Yigit, Murat published the artcileRuthenium(II)-NHC-catalyzed (NHC = perhydrobenzimidazol-2-ylidene) alkylation of amines using the hydrogen borrowing methodology under solvent-free conditions, Formula: C13H14N2O, the publication is Transition Metal Chemistry (Dordrecht, Netherlands) (2019), 44(6), 565-573, database is CAplus.

New ruthenium(II) complexes with N-heterocyclic carbene ligand were synthesized by transmetalation reactions between silver(I) N-heterocyclic carbene complexes and [RuCl₂(p-cymene)]₂. The complexes were characterized by physicochem. and spectroscopic methods. These ruthenium complexes were applied to the N-monoalkylation of aromatic amines with a wide range of primary alcs. under solvent-free conditions using the hydrogen borrowing strategy. The catalytic reactions using all ruthenium complexes resulted in N-monoalkylated products with high selectivities using furfuryl alc. as the alkylating agent.

Transition Metal Chemistry (Dordrecht, Netherlands) published new progress about 52818-63-0. 52818-63-0 belongs to ethers-buliding-blocks, auxiliary class Pyridine,Amine,Benzene,Ether, name is N-(4-Methoxybenzyl)pyridin-2-amine, and the molecular formula is C40H35N7O8, Formula: C13H14N2O.

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