Month: December 2022

Guo, Zufeng published the artcileRapamycin-inspired macrocycles with new target specificity, Recommanded Product: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is Nature Chemistry (2019), 11(3), 254-263, database is CAplus and MEDLINE.

Rapamycin and FK506 are macrocyclic natural products with an extraordinary mode of action, in which they form binary complexes with FK506-binding protein (FKBP) through a shared FKBP-binding domain before forming ternary complexes with their resp. targets, mechanistic target of rapamycin (mTOR) and calcineurin, resp. Inspired by this, we sought to build a rapamycin-like macromol. library to target new cellular proteins by replacing the effector domain of rapamycin with a combinatorial library of oligopeptides. We developed a robust macrocyclization method using ring-closing metathesis and synthesized a 45,000-compound library of hybrid macrocycles (named rapafucins) using optimized FKBP-binding domains. Screening of the rapafucin library in human cells led to the discovery of rapadocin, an inhibitor of nucleoside uptake. Rapadocin is a potent, isoform-specific and FKBP-dependent inhibitor of the equilibrative nucleoside transporter 1 and is efficacious in an animal model of kidney ischemia reperfusion injury. Together, these results demonstrate that rapafucins are a new class of chem. probes and drug leads that can expand the repertoire of protein targets well beyond mTOR and calcineurin.

Nature 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, Recommanded Product: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid.

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

White, James D. published the artcileA concise synthesis of the cytotoxic depsipeptide arenastatin A, Name: (+)-B-Methoxydiisopinocampheylborane, the publication is Tetrahedron Letters (1998), 39(48), 8779-8782, database is CAplus.

Arenastatin A (I) (cryptophycin 24) was synthesized by convergence of hydroxy ester II with amino acid derivative III. Two independent and highly efficient routes to II are disclosed.

Tetrahedron 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 C4Br2N2O4S, Name: (+)-B-Methoxydiisopinocampheylborane.

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

Yoshida, Tatsuki published the artcileN-Methylphenothiazine S-Oxide Enabled Oxidative C(sp²)-C(sp²) Coupling of Boronic Acids with Organolithiums via Phenothiaziniums, Category: ethers-buliding-blocks, the publication is Organic Letters (2021), 23(24), 9664-9668, database is CAplus and MEDLINE.

The development of a transition-metal-free oxidative C(sp²)-C(sp²) coupling of readily available boronic acids RB(OH)₂ (R = Ph, 2-naphthyl, 1-hexenyl, 2-(4-bromophenyl)vinyl, etc.) and organolithiums R¹Li (R¹ = 4-bromophenyl, vinyl, 2-naphthyl, etc.) via phenothiazinium ions I was reported. Various biaryl, styrene, and diene derivatives RR¹ were obtained using this reaction system. The key to this process is N-methylphenothiazine S-oxide (PTZSO), which allows efficient conversion of boronic acids to phenothiazinium ions I. The mechanism of phenothiazinium formation using PTZSO was investigated using theor. calculations and experiments, which provided insight into the unique reactivity of PTZSO.

Organic Letters published new progress about 725251-81-0. 725251-81-0 belongs to ethers-buliding-blocks, auxiliary class Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is (3-Methoxy-5-methylphenyl)boronic acid, and the molecular formula is C8H5F3O3, Category: ethers-buliding-blocks.

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

Jensen, K. A. published the artcileReaction between 5-amino-1,2,3,4-thiatriazole and hydrochloric acid, Name: Formamidine disulfide dihydrochloride, the publication is Acta Chemica Scandinavica (1964), 18(2), 570-2, database is CAplus.

The treatment of monoalkylthioureas with Cl or heating 5-alkylamino-1,2,3,4-thiatriazoles with concentrated HCl 1 hr. at 100° produced derivatives of [RNHC(:NH)S]₂ (I). For example, a cooled saturated solution of NH₂CSNH₂(II) in absolute EtOH treated with Cl gas until the solution yellowed, the mixture filtered, the precipitate dissolved in H₂O, and the solution poured into concentrated HCl gave I.2HCl (R = H) (III), m. 172-4° (the substance was diamagnetic). III obtained from II and from 5-amino-1,2,3,4-thiatriazole (IV) were identical, and this result confirmed earlier conclusions (Sahasrabudhey, CA 45, 8006f). III could be produced from IV via reduction of H₂NC(:NH)S⁺ with HN₃, both pos. ion and acid being formed by hydrolysis of the thiatriazole ring. I (R = Me).2HCl, m. 163-5°, and I (R = Pr).2HCl, m. 155-6°, were also prepared by both methods. l oxidation of tert-BuNHCSNH₂ (V), m. 181°, and the HCl hydrolysis of 5-tert-butylamino-1,2,3,4-thiatriazole produced III. I (R = tert-Bu).2HBr, m. 141-2°, was prepared by the oxidation of V in AcOH with Br in CCl₄.

Acta Chemica Scandinavica 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, Name: Formamidine disulfide dihydrochloride.

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

Hawkins, Paige M. E. published the artcilePotent bactericidal antimycobacterials targeting the chaperone ClpC1 based on the depsipeptide natural products Ecumicin and Ohmyungsamycin A, SDS of cas: 77128-73-5, the publication is Journal of Medicinal Chemistry (2022), 65(6), 4893-4908, database is CAplus and MEDLINE.

Ohmyungsamycin A and ecumicin are structurally related cyclic depsipeptide natural products that possess activity against Mycobacterium tuberculosis (Mtb), the causative agent of tuberculosis (TB). Herein, we describe the design and synthesis of a library of analogs of these two natural products using an efficient solid-phase synthesis and late-stage macrolactamization strategy. Lead analogs possessed potent activity against Mtb in vitro (min. inhibitory concentration 125-500 nM) and were shown to inhibit protein degradation by the mycobacterial ClpC1-ClpP1P2 protease with an associated enhancement of ClpC1 ATPase activity. The most promising analog from the series exhibited rapid bactericidal killing activity against Mtb, capable of sterilizing cultures after 7 days, and retained bactericidal activity against hypoxic non-replicating Mtb. This natural product analog was also active in an in vivo zebrafish model of infection.

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, SDS of cas: 77128-73-5.

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

Wang, Tao published the artcileA Metal-Free Direct Arene C-H Amination, Recommanded Product: 2-Methoxynaphthalene, the publication is Advanced Synthesis & Catalysis (2021), 363(11), 2783-2795, database is CAplus.

Here, a metal-free arene e.g., mesitylene C-H amination using hydroxylamine derivatives 4-(CH₃)C₆H₅S(O)₂ON(R)R¹ (R = H, Me; R¹ = Me, Boc, Bn, etc.) under benign conditions was reported. A charge transfer interaction between the aminating reagents and the arene substrates enables the chemoselective amination of the arene, even in the presence of various functional groups. Oxygen was crucial for an effective conversion and its accelerating role for the electron transfer step was proven exptl. In addition, this was rationalized by a theor. study which indicated the involvement of a dioxygen-bridged complex with a “Sandwich-like” arrangement of the aromatic starting materials and the aminating agents at the dioxygen mol.

Advanced Synthesis & Catalysis 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 C10H14BNO4S, Recommanded Product: 2-Methoxynaphthalene.

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

Nielsen, Daniel S. published the artcileImproving on Nature: Making a Cyclic Heptapeptide Orally Bioavailable, Recommanded Product: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is Angewandte Chemie, International Edition (2014), 53(45), 12059-12063, database is CAplus and MEDLINE.

The use of peptides in medicine is limited by low membrane permeability, metabolic instability, high clearance, and negligible oral bioavailability. The prediction of oral bioavailability of drugs relies on physicochem. properties that favor passive permeability and oxidative metabolic stability, but these may not be useful for peptides. Here we investigate effects of heterocyclic constraints, intramol. hydrogen bonds, and side chains on the oral bioavailability of cyclic heptapeptides. NMR-derived structures, amide H-D exchange rates, and temperature-dependent chem. shifts showed that the combination of rigidification, stronger hydrogen bonds, and solvent shielding by branched side chains enhances the oral bioavailability of cyclic heptapeptides in rats without the need for N-methylation.

Angewandte Chemie, International Edition 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, Recommanded Product: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid.

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

Nakayama, Taku published the artcileWater-promoted dehydrative coupling of 2-aminopyridines in heptane via a borrowing hydrogen strategy, COA of Formula: C13H14N2O, the publication is RSC Advances (2021), 11(37), 23144-23150, database is CAplus and MEDLINE.

A synthetic method for dehydrative N-benzylation promoted by water mols. in heptane using a π-benzylpalladium system has been developed. The presence of water significantly accelerates carbon-nitrogen bond formation, which is accomplished in an atom-economical process to afford the corresponding N-monobenzylated products. A crossover experiment afforded H/D scrambled products, which is consistent with a borrowing hydrogen mechanism. Kinetic isotope effect measurements revealed that benzylic carbon-hydrogen bond cleavage was the rate-determining step.

RSC Advances 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 C13H14N2O, COA of Formula: C13H14N2O.

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

Lebedeva, Daria published the artcileWaste-to-Fuel Approach: Valorization of Lignin from Coconut Coir Pith, Synthetic Route of 134-96-3, the publication is ACS Agricultural Science & Technology (2022), 2(2), 349-358, database is CAplus.

Coconut Coir Pith (CCP) is a relatively unexplored type of lignocellulosic waste from the coconut industry. As a feedstock that is highly enriched in lignin (Klason lignin content of 40.9 wt % found in this study), CCP is a potential source for renewable lignin-derived materials. We have performed a systematic study on the characterization and valorization of lignin from CCP. We have investigated two different valorization approaches: reductive catalytic fractionation (RCF) and soda pulping followed by catalytic hydrodeoxygenation. During RCF, the lignin was converted into monomeric products in 7.6 wt %. Using soda pulping conditions, we were able to isolate lignin from CCP in 74% yield. Subsequent hydrotreatment of the lignin over a Pt/MoO₃/TiO₂ catalyst resulted in the formation of hydrogenated oil in 43 wt % yield, suitable for the production of biobased diesel fuels and lubricant base oils.

ACS Agricultural Science & Technology 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, Synthetic Route of 134-96-3.

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

Rawat, Vishal Kumar published the artcileNickel-Catalyzed Homocoupling of Aryl Ethers with Magnesium Anthracene Reductant, HPLC of Formula: 93-04-9, the publication is Synthesis (2021), 53(18), 3397-3403, database is CAplus.

Nickel-catalyzed reductive homocoupling of aryl ethers has been achieved with Mg(anthracene)(thf)₃ as a readily available low-cost reductant. DFT calculations provided a rationale for the specific efficiency of the diorganomagnesium-type two-electron reducing agent. The calculations show that the dianionic anthracene-9,10-diyl ligand reduces the two aryl ether substrates, resulting in the homocoupling reaction through supply of electrons to the Ni-Mg bimetallic system to form organomagnesium nickel(0)-ate complexes, which cause two sequential C-O bond cleavage reactions. The calculations also showed cooperative actions of Lewis acidic magnesium atoms and electron-rich nickel atoms in the C-O cleavage reactions.

Synthesis 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, HPLC of Formula: 93-04-9.

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