Tag: M.W=200-250

Jin, Jian; Zhang, Kunxiao; Dou, Fei; Hao, Chao; Zhang, Yifang; Cao, Xudong; Gao, Lanchang; Xiong, Jiaying; Liu, Xin; Liu, Bi-Feng; Zhang, Guisen; Chen, Yin published the artcile< Isoquinolinone derivatives as potent CNS multi-receptor D2/5-HT1A/5-HT2A/5-HT6/5-HT7 agents: Synthesis and pharmacological evaluation>, Name: 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole, the main research area is benzoisoxazolyl piperidinyl isoquinolinone preparation multi receptor SAR; aryl piperazinyl isoquinolinone preparation multi receptor SAR; Atypical antipsychotics; Isoquinolinone; Multi-receptor; Piperidine.

IA series of novel Isoquinolinone derivatives were synthesized as potential multi-target antipsychotics. Among these, compound 7-(3-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)pro-poxy)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one showed high affinity for dopamine D2 and serotonin 5-HT1A, 5-HT2A, 5-HT6, and 5-HT7 receptors, showed low affinity for off-target receptors (5-HT2C, H1, and α1), and negligible effects on ether-a-gogo-related gene (hERG; i.e., reduced QT interval prolongation). An animal behavioral study revealed that compound 7-(3-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)pro-poxy)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one reversed APO-induced hyperlocomotion, MK-801-induced hyperactivity, and DOI-induced head twitch. Moreover, compound 7-(3-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)pro-poxy)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one exhibited a high threshold for acute toxicity, a lack of tendency to induce catalepsy, and did not cause prolactin secretion or weight gain when compared to risperidone. Furthermore, in the forced swim test, tail suspension test, and novel object recognition test, treatment with compound 7-(3-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)pro-poxy)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one resulted in improvements in depression and cognitive impairment. In addition, compound 7-(3-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)pro-poxy)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one was favorable pharmacokinetic profile in rats. Thus, the antipsychotic drug-like effects of compound 7-(3-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)pro-poxy)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one indicate that it was useful for developing a novel class of drugs for the treatment of schizophrenia.

European Journal of Medicinal Chemistry published new progress about 5-HT1A receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Name: 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole.

Referemce:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Lu, Bin; Xu, Minghao; Qi, Xiaotian; Jiang, Min; Xiao, Wen-Jing; Chen, Jia-Rong published the artcile< Switchable Radical Carbonylation by Philicity Regulation>, Synthetic Route of 84163-77-9, the main research area is amide preparation; ketoamide preparation; aryl amine cyclicbutane oxime ester carbon monoxide carbonylation photocatalyst.

A new strategy that exploits photoredox catalysis to regulate the philicity of amine coupling partners to drive switchable radical carbonylation reactions was described. In double carbonylation, amines e.g., aniline were first transformed into nitrogen radical cations by single-electron transfer-oxidation and coupled with CO to form carbamoyl radicals, which further underwent radical cross-coupling with the incipient cyanoalkyl acyl radicals to afford the double carbonylation products. Upon the addition of stoichiometric 4-dimethylaminopyridine (DMAP), DMAP competitively traps the initially formed cyanoalkyl acyl radical to form the relatively stabilized cyanoalkyl acyl-DMAP salts that engaged in the subsequent substitution with the nucleophilic amines to produce the single carbonylation products. The reaction proceeded smoothly with excellent selectivity in the presence of various amine nucleophiles at room temperature, generating valuable amides e.g., 4-cyano-N-phenylbutanamide and α-ketoamides e.g., 5-cyano-2-oxo-N-phenylpentanamide in a versatile and controlled fashion. Combined exptl. and computational studies provided mechanistic insights into the possible pathways.

Journal of the American Chemical Societypublished new progress about Amides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Synthetic Route of 84163-77-9.

Referemce:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Favalli, Nicholas; Bassi, Gabriele; Bianchi, Davide; Scheuermann, Jorg; Neri, Dario published the artcile< Large screening of DNA-compatible reaction conditions for Suzuki and Sonogashira cross-coupling reactions and for reverse amide bond formation>, Recommanded Product: 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole, the main research area is alkyne pinacol borane boronic acid DNA synthesis carboxylic acid; Suzuki Sonogashira cross coupling reverse amide formation DNA compatible; DNA-compatible reactions; DNA-encoded libraries; Reverse amide bond formation; Sonogashira cross-coupling; Suzuki cross-coupling.

Progress in DNA-encoded chem. library synthesis and screening crucially relies on the availability of DNA-compatible reactions, which proceed with high yields and excellent purity for a large number of possible building blocks. In the past, exptl. conditions have been presented for the execution of Suzuki and Sonogashira cross-coupling reactions on-DNA. In this article, our aim was to optimize Suzuki and Sonogashira reactions, comparing our results to previously published procedures. We have tested the performance of improved conditions using 606 building blocks (including boronic acids, pinacol boranes and terminal alkynes), achieving >70% conversion for 84% of the tested mols. Moreover, we describe efficient exptl. conditions for the on-DNA synthesis of amide bonds, starting from DNA derivatives carrying a carboxylic acid moiety and 300 primary, secondary and aromatic amines, as amide bonds are frequently found in DNA-encoded chem. libraries thanks to their excellent DNA compatibility.

Bioorganic & Medicinal Chemistrypublished new progress about Boronic acids Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Recommanded Product: 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole.

Referemce:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Zhang, Ze-Xin; Willis, Michael C. published the artcile< Sulfondiimidamides as new functional groups for synthetic and medicinal chemistry>, Reference of 84163-77-9, the main research area is sulfondiimidamide preparation.

Due to their three-dimensional structure, chem. and metabolic stability, polarity, and hydrogen-bonding ability, sulfonamides RS(=NC(CH3)2CH2(CH3)3)(=NNs)R1 (R1 = Et, 4-fluorophenyl, cyclopropyl, pyridin-3-yl, etc. ;NH2, 2-methylpropan-2-aminyl, morpholin-4-yl) occupy a privileged position among the functional groups used to design bioactive mols. The mono aza variants, sulfonimidamides, a functional group known since the 1930s, possess an extra nitrogen atom, which delivers an addnl. point of diversity and introduces chirality at sulfur. The sulfondiimidamides are viable mols. and by using an unsym. sulfurdiimide as a linchpin, in combination with organometallic reagents RMgX (X = Br, Cl) and amines R1NH, their three-component assembly is showed. Variation of the substrates, and the controlled manipulation of nitrogen functionality, allows a broad range of substituents to be introduced at all three nitrogen atoms and at carbon.

Chempublished new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Reference of 84163-77-9.

Referemce:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Wang, Jin-Lin; Liu, Mei-Ling; Zou, Jian-Yu; Sun, Wen-Hui; Liu, Xue-Yuan published the artcile< Copper-Catalyzed Aminoarylation of Alkenes via Aminyl Radical Addition and Aryl Migration>, Name: 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole, the main research area is amino amide preparation; alkene hydroxylamine copper catalyst aminoarylation.

A new strategy for aminoarylation of alkenes by copper-catalyzed Smiles rearrangement using O-benzoylhydroxylamines as the amine reagent was described.. This method affords various β-amino amide derivatives possessing a quaternary carbon center with wide functional group tolerance and high regioselectivity. The mechanistic studies indicate that the transformation can involve aminyl radical intermediates under acid-free condition.

Organic Letterspublished new progress about Amino amides Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Name: 6-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazole.

Referemce:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Paul, Anirudra; Seidel, Daniel published the artcile< α-Functionalization of Cyclic Secondary Amines: Lewis Acid Promoted Addition of Organometallics to Transient Imines>, Reference of 84163-77-9, the main research area is cyclic secondary amine alpha functionalization Lewis acid organometallic imine.

Cyclic imines, generated in situ from their corresponding N-lithiated amines and a ketone hydride acceptor, undergo reactions with a range of organometallic nucleophiles to generate α-functionalized amines in a single operation. Activation of the transient imines by Lewis acids that are compatible with the presence of lithium alkoxides is crucial to accommodate a broad range of nucleophiles including lithium acetylides, Grignard reagents, and aryllithiums with attenuated reactivities.

Journal of the American Chemical Societypublished new progress about Alkali metal alkoxides, lithium alkoxides Role: RGT (Reagent), RACT (Reactant or Reagent). 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, Reference of 84163-77-9.

Referemce:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Gao, Lanchang; Yang, Zhengge; Xiong, Jiaying; Hao, Chao; Ma, Ru; Liu, Xin; Liu, Bi-Feng; Jin, Jian; Zhang, Guisen; Chen, Yin published the artcile< Design, synthesis and biological investigation of flavone derivatives as potential multi-receptor atypical antipsychotics>, HPLC of Formula: 84163-77-9, the main research area is flavone preparation antipsychotic dopamine serotonin receptor; atypical antipsychotics; dopamine; multi-target; serotonin.

The design of a series of novel flavone derivatives I (X = N, CH; Ar = 2-methoxyphenyl, 6-fluorobenzo[d]isoxazol-3-yl, pyrimidin-2-yl, etc.; n = 1, 2), II (m = 1, 2) and III (R1 = H, Cl; R2 = H, Me) was synthesized as potential broad-spectrum antipsychotics by using multi-receptor affinity strategy between dopamine receptors and serotonin receptors. Among them, I (X = CH, Ar = 6-fluorobenzo[d]isoxazol-3-yl, n = 2), (IV) exhibited a promising preclin. profile. Compound IV not only showed high affinity for dopamine D2, D3, and serotonin 5-HT1A, 5-HT2A receptors, but was also endowed with low to moderate activities on 5-HT2C, α1, and H1 receptors, indicating a low liability to induce side effects such as weight gain, orthostatic hypotension and QT prolongation. In vivo behavioral studies suggested that compound IV has favorable effects in alleviating the schizophrenia-like symptoms without causing catalepsy. Taken together, compound V has the potential to be further developed as a novel atypical antipsychotic.

Moleculespublished new progress about 5-HT1A receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 84163-77-9 belongs to class benzisoxazole, and the molecular formula is C12H13FN2O, HPLC of Formula: 84163-77-9.

Referemce:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics