Tag: M.W=200-250

Liu, Jingbo; Shi, Yabing; Tian, Zhicheng; Li, Fengyun; Hao, Zesheng; Wen, Wen; Zhang, Li; Wang, Yuanhong; Li, Yuxin; Fan, Zhijin published the artcile< Bioactivity-Guided Synthesis Accelerates the Discovery of Evodiamine Derivatives as Potent Insecticide Candidates>, HPLC of Formula: 20776-50-5, the main research area is evodiamine derivative preparation insecticide Mythimna Plutella Helicoverpa ryanodine receptor; evodiamine; insecticidal activity; insecticidal mechanism of action, molecular docking; structure−activity relationship.

Pests threaten worldwide food security by decreasing crop yields and damaging their quality. Natural product-based mol. design and structural optimization have been one of the most effective ways to innovate pesticides for integrated insect management. To continue our previous studies on the discovery of insecticidal lead, a series of evodiamine derivatives were designed, synthesized, and evaluated for their insecticidal activities. The bioassay results demonstrated that compounds (I) and (II) exhibited 90 and 80% insecticidal activities against Mythimna separata at 2.5 mg/L, resp., which were superior to evodiamine (10% at 10 mg/L), matrine (45% at 600 mg/L), and rotenone (30% at 200 mg/L). Compounds I, II and (III) showed 90% insecticidal activities against Plutella xylostella at 1.0 mg/L, far more potent than those of evodiamine, matrine, and rotenone. Compound I displayed 60% insecticidal activity against Helicoverpa armigera at 5.0 mg/L, while evodiamine, matrine, and rotenone showed very poor activities. The study on the insecticidal mechanism of action by a calcium imaging experiment indicated that the insect ryanodine receptors (RyRs) could be the potential target of I. Furthermore, the mol. docking indicated that I anchored in the binding site of the RyR of P. xylostella. The above results manifested the potential of evodiamine derivatives as potent insecticide candidates.

Journal of Agricultural and Food Chemistry published new progress about Helicoverpa armigera. 20776-50-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H6BrNO2, HPLC of Formula: 20776-50-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Afewerki, Samson; Breistein, Palle; Pirttila, Kristian; Deiana, Luca; Dziedzic, Pawel; Ibrahem, Ismail; Cordova, Armando published the artcile< Catalytic Enantioselective β-Alkylation of α,β-Unsaturated Aldehydes by Combination of Transition-Metal- and Aminocatalysis: Total Synthesis of Bisabolane Sesquiterpenes>, Recommanded Product: 3-(4-Bromophenyl)acrylaldehyde, the main research area is bisabolane sesquiterpene curcumene tumerone dehydrocurcumene enantioselective synthesis; unsaturated aldehyde asym beta alkylation.

The first example of enantioselective β-alkylation of α,β-unsaturated aldehydes by combination of aminocatalysis and transition-metal catalysis is reported. The catalyzed asym. 1,4-addition gave the corresponding β-alkyl aldehydes with up to 98:2 e.r. Thus, simple bench stable chiral amines can be used as catalyst in combination with a copper salt without the use of a glove box to achieve catalytic asym. addition of dialkylzinc reagents to enals with high enantioselectivity. The novel co-catalytic reaction was utilized as the key step for the expeditious total synthesis of bisabolane sesquiterpenes, e.g. I.

Chemistry – A European Journal published new progress about 1,4-Addition reaction. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Recommanded Product: 3-(4-Bromophenyl)acrylaldehyde.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

DeLeon, Chelsea; Pemberton, Kyle; Green, Michael; Kalajdzic, Vanja; Rosato, Martina; Xu, Fenglian; Arnatt, Christopher published the artcile< Novel GPER Agonist, CITFA, Increases Neurite Growth in Rat Embryonic (E18) Hippocampal Neurons>, Recommanded Product: 2-Bromo-4-isopropylaniline, the main research area is GPER GPER30 agonist CITFA neurite growth hippocampus antagonist neurodevelopment; Estrogen; G-protein coupled estrogen receptor (GPER/GPR30); agonist; antagonist neurodevelopment; calcium signaling; embryonic primary culture; hippocampus; neurite outgrowth.

Numerous studies have reported neuroprotective and procognitive effects of estrogens. The estrogen 17β-estradiol (E2) activates both the classical nuclear estrogen receptors ERα and ERβ as well as the G protein-coupled estrogen receptor (GPER). The differential effects of targeting the classical estrogen receptors over GPER are not well-understood. A limited number of selective GPER compounds have been described. In this study, 10 novel compounds were synthesized and exhibited half-maximal effective concentration values greater than the known GPER agonist G-1 in calcium mobilization assays performed in nonadherent HL-60 cells. Of these compounds, 2-cyclohexyl-4-isopropyl-N-((5-(tetrahydro-2H-pyran-2-yl)furan-2-yl)methyl)aniline, referred to as CITFA, significantly increased axonal and dendritic growth in neurons extracted from embryonic day 18 (E18) fetal rat hippocampal neurons. Confirmation of the results was performed by treating E18 hippocampal neurons with known GPER-selective antagonist G-36 and challenging with either E2, G-1, or CITFA. Results from these studies revealed an indistinguishable difference in neurite outgrowth between the treatment and control groups, exhibiting that neurite outgrowth in response to G-1 and CITFA originates from GPER activation and can be abolished with pretreatment of an antagonist. Subsequent docking studies using a homol. model of GPER showed unique docking poses between G-1 and CIFTA. While docking poses differed between the ligands, CIFTA exhibited more favorable distance, bond angle, and strain for hydrogen-bonding and hydrophobic interactions.

ACS Chemical Neuroscience published new progress about Biological ion transport, calcium. 51605-97-1 belongs to class bromides-buliding-blocks, and the molecular formula is C9H12BrN, Recommanded Product: 2-Bromo-4-isopropylaniline.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Kil, Kun-Eek; Poutiainen, Pekka; Zhang, Zhaoda; Zhu, Aijun; Choi, Ji-Kyung; Jokivarsi, Kimmo; Brownell, Anna-Liisa published the artcile< Radiosynthesis and Evaluation of an 18F-Labeled Positron Emission Tomography (PET) Radioligand for Metabotropic Glutamate Receptor Subtype 4 (mGlu4)>, COA of Formula: C8H3BrO3, the main research area is fluorine labeled PET radioligand metabotropic glutamate receptor subtype 4; chlorophenylpicolinamide phthalimide derivative fluorine labeled PET radioligand mGlu4.

Four 4-phthalimide derivatives of N-(3-chlorophenyl)-2-picolinamide were synthesized as potential ligands for the PET imaging of mGlu4 in the brain. Of these compounds, N-(3-chloro-4-(4-fluoro-1,3-dioxoisoindolin-2-yl)phenyl)-2-picolinamide (3, III, KALB001) exhibited improved binding affinity (IC50 = 5.1 nM) compared with ML128 (1, I) and was subsequently labeled with 18F. When finally formulated in 0.1 M citrate buffer (pH 4) with 10% ethanol, the specific activity of [18F]3 at the end of synthesis (EOS) was 233.5 ± 177.8 GBq/μmol (n = 4). The radiochem. yield of [18F]3 was 16.4 ± 4.8% (n = 4), and the purity was over 98%. In vivo imaging studies in a monkey showed that the radiotracer quickly penetrated the brain with the highest accumulation in the brain areas known to express mGlu4. Despite some unfavorable radiotracer properties like fast washout in rodent studies, [18F]3 is the first 18F-labeled mGlu4 radioligand, which can be further modified to improve pharmacokinetics and brain penetrability for future human studies.

Journal of Medicinal Chemistry published new progress about Allosterism. 82-73-5 belongs to class bromides-buliding-blocks, and the molecular formula is C8H3BrO3, COA of Formula: C8H3BrO3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Soucy, C.; Favreau, D.; Kayser, M. M. published the artcile< The regioselectivity of metal hydride reductions of 3-substituted phthalic anhydrides>, Category: bromides-buliding-blocks, the main research area is phthalide substituted; phthalic anhydride substituted hydride reduction; regiochem reduction substituted phthalic anhydride.

The reduction of 3-methoxyphthalide by metal hydrides was reinvestigated. Various effects controlling selectivity of reductions in 3-substituted phthalides were studied, and a qual. interpretation of the results was proposed. Methods for obtaining enhanced yields of one or the other lactonic product were developed.

Journal of Organic Chemistry published new progress about LUMO (molecular orbital). 82-73-5 belongs to class bromides-buliding-blocks, and the molecular formula is C8H3BrO3, Category: bromides-buliding-blocks.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

White, Nicholas A.; Rovis, Tomislav published the artcile< Oxidatively Initiated NHC-Catalyzed Enantioselective Synthesis of 3,4-Disubstituted Cyclopentanones from Enals>, Formula: C9H7BrO, the main research area is NHC catalyst oxidative enantioselective cyclization aryl enal; cyclopentanone stereoselective preparation.

An unprecedented N-heterocyclic carbene (NHC)-catalyzed annulation of enals to form 3,4-disubstituted cyclopentanones, e.g. I, has been discovered. Aryl enals undergo dimerization in the presence of a single-electron oxidant to form C2 sym. cyclopentanones. A cross-reaction has also been developed, allowing for the synthesis of differentially substituted cyclopentanones. Mechanistically, the reaction is thought to proceed through radical intermediates, further establishing the synthetic utility of this class of reactivity.

Journal of the American Chemical Society published new progress about Enantioselective synthesis. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Formula: C9H7BrO.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Geng, Zhi-Cong; Zhang, Shao-Yun; Li, Nai-Kai; Li, Ning; Chen, Jian; Li, Hai-Yan; Wang, Xing-Wang published the artcile< Organocatalytic Diversity-Oriented Asymmetric Synthesis of Tricyclic Chroman Derivatives>, Application In Synthesis of 3893-18-3, the main research area is diphenylprolinol trimethylsilyl ether catalyst Michael aldol Diels Alder reaction; hydroxyaryloxobutenoate enal aldol Diels Alder reaction; organocatalytic diversity oriented asym synthesis tricyclic chroman derivative.

The tandem oxo-Michael-IED/HDA (inverse-electron-demand hetero-Diels-Alder) and oxo-Michael-IED/HDA-Michael-Aldol condensation transformations between (E)-2-hydroxyaryl-2-oxobut-3-enoate derivatives with enals have been developed in the presence of (S)-diphenylprolinol trimethylsilyl ether as an organocatalyst. Two types of tricyclic chroman derivatives, e.g. I and II, were, resp., obtained, by adjusting the reactant ratio and reaction temperature, in good yields (up to 96%) with excellent enantioselectivities (up to >99%) and good diastereoselectivities (up to >30/1). It should be noted that the divergent chiral chroman derivatives were obtained by successive reaction of (E)-2-hydroxyaryl-2-oxobut-3-enoate derivatives with two different enal substrates in highly catalytic results.

Journal of Organic Chemistry published new progress about Aldol condensation. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Application In Synthesis of 3893-18-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Akester, Jessica N.; Njaria, Paul; Nchinda, Aloysius; Le Manach, Claire; Myrick, Alissa; Singh, Vinayak; Lawrence, Nina; Njoroge, Mathew; Taylor, Dale; Moosa, Atica; Smith, Anthony J.; Brooks, Elizabeth J.; Lenaerts, Anne J.; Robertson, Gregory T.; Ioerger, Thomas R.; Mueller, Rudolf; Chibale, Kelly published the artcile< Synthesis, Structure-Activity Relationship, and Mechanistic Studies of Aminoquinazolinones Displaying Antimycobacterial Activity>, Safety of 2-Amino-4-bromobenzoic acid, the main research area is aminoquinazolinone preparation Mycobacterium tuberculosis pharmacokinetic SAR Suzuki antimycobacterial; 2-aminoquinazolinones; Mycobacterium tuberculosis; drug discovery; tuberculosis.

Phenotypic whole-cell screening against Mycobacterium tuberculosis (Mtb) in glycerol-alanine-salts supplemented with Tween 80 and iron (GASTE-Fe) media led to the identification of a 2-aminoquinazolinone hit compound, sulfone which was optimized for solubility by replacing the sulfone moiety with a sulfoxide I. The synthesis and structure-activity relationship (SAR) studies identified several compounds with potent antimycobacterial activity, which were metabolically stable and noncytotoxic. Compound I displayed favorable in vitro properties and was therefore selected for in vivo pharmacokinetic (PK) studies where it was found to be extensively metabolized to the sulfone. Both derivatives exhibited promising PK parameters; however, when I was evaluated for in vivo efficacy in an acute TB infection mouse model, it was found to be inactive. In order to understand the in vitro and in vivo discrepancy, compound I was subsequently retested in vitro using different Mtb strains cultured in different media. This revealed that activity was only observed in media containing glycerol and led to the hypothesis that glycerol was not used as a primary carbon source by Mtb in the mouse lungs, as has previously been observed Support for this hypothesis was provided by spontaneous-resistant mutant generation and whole genome sequencing studies, which revealed mutations mapping to glycerol metabolizing genes indicating that the 2-aminoquinazolinones kill Mtb in vitro via a glycerol-dependent mechanism of action.

ACS Infectious Diseases published new progress about Antimycobacterial agents. 20776-50-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H6BrNO2, Safety of 2-Amino-4-bromobenzoic acid.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Yukawa, Yasuhide; Tsuno, Yuho; Sawada, Masami published the artcile< Resonance effect in Hammett relation. IV. Linear free energy based on the normal substituent constants>, COA of Formula: C10H11BrO2, the main research area is RESONANCE EFFECT HAMMETT RELATION; HAMMETT RELATION RESONANCE EFFECT; SUBSTITUENT CONST FREE ENERGY.

A set of normal substituent constants, σ0, was derived from the rates of alk. hydrolysis of m- and p-substituted Et phenylacetates in 60% Me2CO at 25.0°. The values of the σ0 constants obtained were generally identical with Taft’s values within exptl. uncertainty. On the basis of the derived σ0, substituent effects on the general electrophilic reactions were related excellently by the equation log k/k0 = ρ(σ0 + rΔ σR+), where ΔσR+ corresponds to the exaltation of Brown and Okamoto’s σ+ from σ0 (CA 53, 9120f). Similar treatment could also be applied to the nucleophilic reactions. The utility of this equation for the estimation of resonance contribution and for the consideration of reaction mechanisms is discussed.

Bulletin of the Chemical Society of Japan published new progress about Hydrolysis kinetics. 14062-30-7 belongs to class bromides-buliding-blocks, and the molecular formula is C10H11BrO2, COA of Formula: C10H11BrO2.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary