Month: December 2022

Ma, Liangwei published the artcilePhoto-controlled fluorescence on/off switching of a pseudo[3]rotaxane between an AIE-active pillar[5]arene host and a photochromic bithienylethene guest, Synthetic Route of 219537-97-0, the publication is Chemical Communications (Cambridge, United Kingdom) (2018), 54(19), 2405-2408, database is CAplus and MEDLINE.

A fluorescence photo-switch was constructed based on a host-guest pseudo[3]rotaxane between an AIE-active pillar[5]arene host bearing tetra-Ph ethylene moieties and a photo-responsive dithienylethylene guest containing two cyano-triazole branches. Its fluorescence on/off switching could be controlled by the photochromism reaction of the dithienylethylene unit.

Chemical Communications (Cambridge, United Kingdom) published new progress about 219537-97-0. 219537-97-0 belongs to chlorides-buliding-blocks, auxiliary class Fused/Partially Saturated Cycles,Cyclopentenes, name is 5-Chloro-3-[2-(5-chloro-2-methylthien-3-yl)cyclopent-1-en-1-yl]-2-methylthiophene, and the molecular formula is C15H14Cl2S2, Synthetic Route of 219537-97-0.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Wang, Shuai published the artcileStructure-Based Design, Synthesis, and Biological Evaluation of New Triazolo[1,5-a]Pyrimidine Derivatives as Highly Potent and Orally Active ABCB1 Modulators, Computed Properties of 939-99-1, the publication is Journal of Medicinal Chemistry (2020), 63(24), 15979-15996, database is CAplus and MEDLINE.

ABCB1 is a promising therapeutic target for overcoming multidrug resistance (MDR). In this work, we reported the structure-based design of triazolo[1,5-a]pyrimidines as new ABCB1 modulators, of which WS-691 significantly increased sensitization of ABCB1-overexpressed SW620/Ad300 cells to paclitaxel (PTX) (IC₅₀ = 22.02 nM). Mechanistic studies indicated that WS-691 significantly increased the intracellular concentration of PTX and [³H]-PTX while decreasing the efflux of [³H]-PTX in SW620/Ad300 cells by inhibiting the efflux function of ABCB1. The cellular thermal shift assay suggested that WS-691 could stabilize ABCB1 by directly binding to ABCB1. WS-691 could stimulate the activity of ABCB1 ATPase but had almost no inhibitory activity against CYP3A4. Importantly, WS-691 increased the sensitivity of SW620/Ad300 cells to PTX in vivo without observed toxicity. Collectively, WS-691(I) is a highly potent and orally active ABCB1 modulator capable of overcoming MDR. The triazolo[1,5-a]pyrimidine may be a promising scaffold for developing more potent ABCB1 modulators.

Journal of Medicinal Chemistry published new progress about 939-99-1. 939-99-1 belongs to chlorides-buliding-blocks, auxiliary class Fluoride,Chloride,Benzyl chloride,Benzene, name is 1-(Chloromethyl)-4-(trifluoromethyl)benzene, and the molecular formula is C13H10O3, Computed Properties of 939-99-1.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Shen, Chong published the artcileCatalytic Asymmetric Umpolung Allylation/2-Aza-Cope Rearrangement for the Construction of α-Tetrasubstituted α-Trifluoromethyl Homoallylic Amines, COA of Formula: C8H4ClF3O, the publication is Organic Letters (2019), 21(17), 6940-6945, database is CAplus and MEDLINE.

A general protocol for the preparation of enantioenriched α-tetrasubstituted α-trifluoromethyl homoallylic amines (R)-F₃CCR(NH₂)CH₂CH:CHR¹ (R = Ph, 4-ClC₆H₄, 2-naphthyl, etc., R¹ = Ph, 3-MeC₆H₄, 2-thienyl, etc.) and (S)-F₃CCH(NH₂)CH₂CH:CHR² (R² = Ph, 3-MeC₆H₄, 2-furyl, 6-quinolinyl, etc.) is disclosed. Despite the significant challenge in stereoselectivity control, Ir-catalyzed asym. cascade umpolung allylation/2-aza-Cope rearrangement of trifluoromethylated fluorenone imines with allylic carbonates was realized with excellent efficiency and remarkable stereoselectivity. These were enabled by the suitable protective imino moiety and an unexpectedly exclusive E-geometrical imine of the allylation intermediate. This methodol. is also applicable to facile access to chiral α-trisubstituted α-trifluoromethyl homoallylic amines in similarly high yield and stereoselectivity.

Organic Letters published new progress about 5860-95-7. 5860-95-7 belongs to chlorides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Chloride,Benzene,Ketone, name is 1-(2-Chlorophenyl)-2,2,2-trifluoroethanone, and the molecular formula is C13H9FO2, COA of Formula: C8H4ClF3O.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Zhu, Chen published the artcileMild and Rapid Hydroxylation of Aryl/Heteroaryl Boronic Acids and Boronate Esters with N-Oxides, Product Details of C7H8BClO2, the publication is Organic Letters (2012), 14(13), 3494-3497, database is CAplus and MEDLINE.

Aryl and heteroaryl boronic acids and boronate esters are rapidly, often within minutes, transformed into the corresponding phenols by N-oxides in an open flask at ambient temperature This transformation has broad compatibility with a variety of functional groups.

Organic Letters published new progress about 209919-30-2. 209919-30-2 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-Chloro-2-methylphenylboronic acid, and the molecular formula is C6H10F3NO, Product Details of C7H8BClO2.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Xu, Yanjun published the artcilePyridine derivatives(X): synthesis and herbicidal activities of 2-sec-butylamino-5-(2-aryloxy-4-pyridinyl)-4-yl)-1,3,4-thiadiazoles, Application of 2-Chloroisonicotinic acid, the publication is Nongyaoxue Xuebao (2007), 9(2), 189-192, database is CAplus.

A method for the synthesis of the title compounds [i.e., N-(1-methylpropyl)-5-[2-(phenoxy)-4-pyridinyl]-1,3,4-thiadiazol-2-amine derivatives] is reported here. 2-(Sec-butylamino)-5-(2-chloro-4-pyridinyl)-1,3,4-thiadiazole (BCPT) is a lead compound for herbicide development. In order to improve its herbicidal activity and study the relationship between chem. structure and bioactivity, an aryl ether moiety was introduced to the sketch. A new series of compounds was synthesized and the structures were confirmed by NMR and elementary anal. A preliminary bioassay showed that all the synthesized compounds showed a poor inhibition rate (0-45%) at 500 mg/L, much weaker than (BCPT) (72%-87%). A chloro-atom on the 2-position of pyridine ring may be indispensable for herbicidal activity.

Nongyaoxue Xuebao published new progress about 6313-54-8. 6313-54-8 belongs to chlorides-buliding-blocks, auxiliary class Pyridine,Chloride,Carboxylic acid, name is 2-Chloroisonicotinic acid, and the molecular formula is C6H8O4, Application of 2-Chloroisonicotinic acid.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Yang, Peng published the artcileEnantioselective Dearomative [3 + 2] Umpolung Annulation of N-Heteroarenes with Alkynes, Application of (2-Bromo-4-chlorophenyl)boronic acid, the publication is Journal of the American Chemical Society (2022), 144(3), 1087-1093, database is CAplus and MEDLINE.

Enantioselective [3 + 2] annulation of N-heteroarenes such as 2-(2-bromophenyl)quinoline with alkynes R¹CCR² [R¹ = Me, Ph, benzyloxymethyl, (thiophen-2-ylmethoxy)methyl, etc.; R² = Me, Ph, benzyloxymethyl, (thiophen-2-ylmethoxy)methyl, etc.] has been developed via a cobalt-catalyzed dearomative umpolung strategy in the presence of chiral ligand e.g., [(2R,3R)-3-(diphenylphosphanyl)butan-2-yl]diphenylphosphane and reducing reagent. A variety of electron-deficient N-heteroarenes e.g., 2-(2-bromophenyl)quinoline and internal or terminal alkynes are employed in this reaction, showing a broad substrate scope and good functionality tolerance. Annulation of electron-rich indoles I (R = H, 5-Cl) with alkynes is also developed. This protocol provides a straightforward access to a variety of N-spiroheterocyclic mols. such as II and in excellent enantioselectivities (76 examples, up to 99% ee).

Journal of the American Chemical Society published new progress about 1451393-45-5. 1451393-45-5 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Bromide,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is (2-Bromo-4-chlorophenyl)boronic acid, and the molecular formula is C20H17FO4S, Application of (2-Bromo-4-chlorophenyl)boronic acid.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Chen, Shuqing published the artcileRedox-neutral ortho-C-H amination of pinacol arylborates via palladium(II)/norbornene catalysis for aniline synthesis, Recommanded Product: 2-(4-Chloro-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, the publication is Chemical Science (2019), 10(36), 8384-8389, database is CAplus and MEDLINE.

A palladium(II)/norbornene cooperative catalysis enabled redox-neutral ortho-C-H amination of pinacol aryl- or heteroarylborates for the synthesis of structurally diverse anilines was reported. The method was scalable, robust (tolerance of air and moisture), phosphine ligand-free and compatible with a wide range of functionalities. These practical features made this reaction amenable for industry. A plethora of synthetically very useful halogenated anilines which often cannot be prepared via other transition-metal-catalyzed aminations were readily produced using this method. Particularly, the orthogonal reactivity between pinacol arylborates and aryl iodides was demonstrated. Preliminary deuterium-labeling studies revealed a redox-neutral ipso-protonation mechanism of this process, which will surely inspire the future development of this field. Overall, the exceptionally broad scope (47 examples) and reliability of this procedure, together with the wide availability of pinacol arylborates made this chem. a valuable addition to the existing methods for aniline synthesis.

Chemical Science published new progress about 1030832-75-7. 1030832-75-7 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Boronic acid and ester,Benzene,Boronate Esters,Boronic acid and ester, name is 2-(4-Chloro-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C13H18BClO2, Recommanded Product: 2-(4-Chloro-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Yuan, Huihui published the artcileA solvent-free method for the preparation of phosphinates from P(O)-OH compounds with alkyl chlorides, Name: 3-Chlorobenzylchloride, the publication is Tetrahedron Letters (2021), 153529, database is CAplus.

Herein, a new solvent-free synthetic method using P(O)-OH compound and alkyl chloride for phosphinate compounds is disclosed. This transformation proceeds smoothly under the promotion of a lone base and presents the advantages of an easily available raw material source, a simple post treatment process, good functional group tolerance and high reaction efficiency. Good yield was obtained when the reaction was magnified to gram scale(coating), and the molar ratio of P(O)-OH compounds and alkyl chlorides can be decreased to 1:2. This protocol provides a practical method for the preparation of phosphorus derivatives Furthermore, the reaction mechanism was explored by ³¹P NMR.

Tetrahedron Letters published new progress about 620-20-2. 620-20-2 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Benzyl chloride,Benzene, name is 3-Chlorobenzylchloride, and the molecular formula is C9H13NO2, Name: 3-Chlorobenzylchloride.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Wang, Pei-Yi published the artcileRational Optimization and Action Mechanism of Novel Imidazole (or Imidazolium)-Labeled 1,3,4-Oxadiazole Thioethers as Promising Antibacterial Agents against Plant Bacterial Diseases, Safety of 3-Chlorobenzylchloride, the publication is Journal of Agricultural and Food Chemistry (2019), 67(13), 3535-3545, database is CAplus and MEDLINE.

The emergence and widespread occurrence of plant bacterial diseases that cause global production constraints have become major challenges to agriculture worldwide. To promote the discovery and development of new bactericides, imidazole-labeled 1,3,4-oxadiazole thioethers were first fabricated by integrating the crucially bioactive scaffolds of the imidazole motif and 1,3,4-oxadiazole skeleton in a single mol. architecture. Subsequently, a superior antibacterial compound A₆ was gradually discovered possessing excellent competence against plant pathogens Xanthomonas oryzae pv oryzae and Xanthomonas axonopodis pv citri with EC₅₀ values of 0.734 and 1.79 μg/mL, resp. These values were better than those of com. agents bismerthiazol (92.6 μg/mL) and thiodiazole copper (77.0 μg/mL). Further modifying the imidazole moiety into the imidazolium scaffold led to the discovery of an array of potent antibacterial compounds providing the corresponding min. EC₅₀ values of 0.295 and 0.607 μg/mL against the two strains. Moreover, a plausible action mechanism for attacking pathogens was proposed based on the concentration dependence of SEM, transmission electron microscopy, and fluorescence microscopy images. Given the simple mol. structures, easy synthetic procedure, and highly efficient bioactivity, imidazole (or imidazolium)-labeled 1,3,4-oxadiazole thioethers can be further explored and developed as promising indicators for the development of com. drugs.

Journal of Agricultural and Food Chemistry published new progress about 620-20-2. 620-20-2 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Benzyl chloride,Benzene, name is 3-Chlorobenzylchloride, and the molecular formula is C18H35NO, Safety of 3-Chlorobenzylchloride.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Fronk, Stephanie L. published the artcileEffect of chiral 2-ethylhexyl side chains on chiroptical properties of the narrow bandgap conjugated polymers PCPDTBT and PCDTPT, COA of Formula: C10H15ClO3S, the publication is Chemical Science (2016), 7(8), 5313-5321, database is CAplus and MEDLINE.

Two narrow bandgap conjugated polymers containing chiral 2-ethylhexyl side chains were synthesized: poly[(4,4-bis(2-ethylhexyl)cyclopenta-[2,1-b:3,4-b‘]dithiophene)-2,6-diyl-alt-(2,1,3-benzothiadiazole)-4,7-diyl] (PCPDTBT*) and poly[(4,4-bis(2-ethylhexyl)cyclopenta[2,1-b:3,4-b‘]dithiophene)-2,6-diyl-alt-[1,2,5]-thiadiazolo[3,4-c]pyridine] (PCDTPT*). The presence of a chiral substituent provides a handle to study the geometry of interchain aggregates and/or the secondary structure of these conjugated polymers in solution and in thin films via CD spectroscopy, provided that the asymmetry in the side-chain was translated to the optically active conjugated backbone. CD signals were observed for PCPDTBT* and PCDTPT* in poor solvent systems, which indicated the presence of chiral ordering in the aggregates. PCPDTBT* showed greater chiral order than PCDTPT* based on their relative anisotropy factors. Addnl., GIWAXS anal. reveals that PCPDTBT* films were more ordered than what was observed for the same polymer containing racemic 2-ethylhexyl chains. Upon solution deposition, the chiral ordering was found to translate to the solid-state microstructure for PCPDTBT* but not PCDTPT*. The presence of a pyridyl nitrogen on the thiadiazolo[3,4-c]pyridine ring of PCDTPT* favored a planar conformation for the backbone such that it has a higher rotational barrier compared to PCPDTBT*. This larger rotational barrier appeared to limit the ability of PCDTPT* to adopt a helical structure or relevant chain distortions for achieving chiral aggregates.

Chemical Science published new progress about 21286-54-4. 21286-54-4 belongs to chlorides-buliding-blocks, auxiliary class Chiral,Chloride,Sulfonyl chlorides,Aliphatic cyclic hydrocarbon,Ketone, name is ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride, and the molecular formula is C10H15ClO3S, COA of Formula: C10H15ClO3S.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics