Month: February 2023

Copper(I)-catalyzed site-selective C(sp³)-H bond chlorination of ketones, (E)-enones and alkylbenzenes by dichloramine-T was written by Jin, Jianwen;Zhao, Yichao;Kyne, Sara Helen;Farshadfar, Kaveh;Ariafard, Alireza;Chan, Philip Wai Hong. And the article was included in Nature Communications in 2021.Recommanded Product: 4-Bromo-N-methoxy-N-methylbenzamide This article mentions the following:

Here, a copper(I)-catalyzed synthetic method for the efficient site-selective C(sp³)-H bond chlorination of ketones, (E)-enones and alkylbenzenes by dichloramine-T at room temperature were reported. A key feature of the broad substrate scope is tolerance to unsaturation, which would normally pose an immense challenge in chemoselective aliphatic C-H bond functionalization. By unlocking dichloramine-T’s potential as a chlorine radical atom source, the product site-selectivities achieved were among the most selective in alkane functionalization and should find widespread utility in chem. synthesis. This was exemplified by the late-stage site-selective modification of a number of natural products and bioactive compounds and gram-scale preparation and formal synthesis of two drug mols. In the experiment, the researchers used many compounds, for example, 4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2Recommanded Product: 4-Bromo-N-methoxy-N-methylbenzamide).

4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. The presence of the amide group –C(=O)N– is generally easily established, at least in small molecules. It can be distinguished from nitro and cyano groups in IR spectra. Amides exhibit a moderately intense νCO band near 1650 cm−1. By 1H NMR spectroscopy, CONHR signals occur at low fields. In X-ray crystallography, the C(=O)N center together with the three immediately adjacent atoms characteristically define a plane.Recommanded Product: 4-Bromo-N-methoxy-N-methylbenzamide

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

Regioselective Synthesis of Enones via a Titanium-Promoted Coupling of Unsymmetrical Alkynes with Weinreb Amides was written by Silwal, Sajan;Rahaim, Ronald J.. And the article was included in Journal of Organic Chemistry in 2014.Application of 116332-61-7 This article mentions the following:

A modular titanium-promoted coupling of unsym. internal alkynes with Weinreb amides is described. The coupling reaction takes place at room temperature and affords E-trisubstituted enones in moderate to good yields with high levels of regioselectivity. E.g., in presence of Ti(OiPr)₄ and i-PrMgCl in Et₂O at room temperature, coupling of 1-phenyl-1-propyne and 4-FC₆H₄CONMeOMe gave 60% (E)-I. The system shows moderate chemoselectivity. In the experiment, the researchers used many compounds, for example, N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7Application of 116332-61-7).

N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7) belongs to amides. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well. Thus amides can participate in hydrogen bonding with water and other protic solvents; the oxygen atom can accept hydrogen bonds from water and the N–H hydrogen atoms can donate H-bonds. Ionic, or saltlike, amides are strongly alkaline compounds ordinarily made by treating ammonia, an amine, or a covalent amide with a reactive metal such as sodium.Application of 116332-61-7

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

Synthesis of 2-(2-Hydroxyaryl)-4H-benzo[e][1,3]oxazin-4-ones by Palladium-Catalyzed C(sp²)-H Hydroxylation via Electro-chemical Oxidation was written by Wu, Hongfeng;An, Qi;He, Chaoyin;Fan, Xiaodong;Guo, Weihao;Zuo, Minghui;Xu, Chunzhao;Guo, Rui;Chu, Wenyi;Sun, Zhizhong. And the article was included in Advanced Synthesis & Catalysis in 2020.Related Products of 49667-22-3 This article mentions the following:

An electrochem. direct ortho-hydroxylation of 2-aryl-4H-benzo[e][1,3]oxazin-4-ones I (R¹ = Ph, 4-chlorophenyl, 2-naphthyl, furan-3-yl, etc.; R² = H, 7-Me, 6-Cl, etc.) was developed with Pd(OAc)₂ as catalyst, oxazine ring as a directing group and Oxone as the hydroxylation reagent. A series of hydroxylation products II (R³ = 2-hydroxyphenyl, 2-hydroxy-4-chlorophenyl, 2-hydroxyfuran-3-yl, etc.) was obtained under mild conditions, and the yields were from medium to good. This method is characterized by good functional group tolerance and a wide range of substrates. More importantly, anodic oxidation is used to avoid the use of potentially toxic and polluting oxidants. A gram-scale direct electrochem. hydroxylation of 2-phenyl-4H-benzo[e][1,3]oxazin-4-one was performed, and the hydroxylation product, 2-(2-hydroxyphenyl)-4H-benzo[e][1,3]oxazin-4-one was applied to synthesize the drug deferasirox. In addition, the single crystal of 2-(2-hydroxyphenyl)-4H-benzo[e][1,3]oxazin-4-one was obtained and determined by X-ray diffraction. Finally, the reaction mechanism was proposed and verified by cyclic voltammetry (CV). This protocol also provides an alternative electrochem. hydroxylation methodol. for the functionalization of mols. In the experiment, the researchers used many compounds, for example, 2-Hydroxy-4-methylbenzamide (cas: 49667-22-3Related Products of 49667-22-3).

2-Hydroxy-4-methylbenzamide (cas: 49667-22-3) belongs to amides. Amides can be viewed as a derivative of a carboxylic acid RC(=O)OH with the hydroxyl group –OH replaced by an amine group −NR′R″; or, equivalently, an acyl (alkanoyl) group RC(=O)− joined to an amine group. In simple aromatic amides, fragmentation occurs on both sides of the carbonyl group. If a hydrogen is available in N-substituted aromatic amides, it tends to migrate and form an aromatic amine and the loss of a ketene.Related Products of 49667-22-3

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

Examination of SOD1 aggregation modulators and their effect on SOD1 enzymatic activity as a proxy for potential toxicity was written by Malik, Ravinder;Corrales, Christian;Linsenmeier, Miriam;Alalami, Huda;Sepanj, Niki;Bitan, Gal. And the article was included in FASEB Journal in 2020.Computed Properties of C18H17NO5 This article mentions the following:

Small-mol. inhibitors of abnormal protein self-assembly are promising candidates for developing therapy against proteinopathies. Such compounds have been examined primarily as inhibitors of amyloid β-protein (Aβ), whereas testing of inhibitors of other amyloidogenic proteins has lagged behind. An important issue with screening compound libraries is that although an inhibitor suitable for therapy must be both effective and nontoxic, typical screening focuses on efficacy, whereas safety typically is tested at a later stage using cells and/or animals. In addition, typical thioflavin T (ThT)-fluorescence-based screens use the final fluorescence value as a readout, potentially missing important kinetic information. Here, we examined potential inhibitors of superoxide dismutase 1 (SOD1) using ThT-fluorescence including the different phases of fluorescence change and added a parallel screen of SOD1 activity as a potential proxy for compound toxicity. Some compounds previously reported to inhibit other amyloidogenic proteins also inhibited SOD1 aggregation at low micromolar concentrations, whereas others were ineffective. Anal. of the lag phase and exponential slope added important information that could help exclude false-pos. or false-neg. results. SOD1 was highly resistant to inhibition of its activity, and therefore, did not have the necessary sensitivity to serve as a proxy for examining potential toxicity. In the experiment, the researchers used many compounds, for example, 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8Computed Properties of C18H17NO5).

2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8) belongs to amides. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well. Thus amides can participate in hydrogen bonding with water and other protic solvents; the oxygen atom can accept hydrogen bonds from water and the N–H hydrogen atoms can donate H-bonds. In simple aromatic amides, fragmentation occurs on both sides of the carbonyl group. If a hydrogen is available in N-substituted aromatic amides, it tends to migrate and form an aromatic amine and the loss of a ketene.Computed Properties of C18H17NO5

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

Novel acylureidoindolin-2-one derivatives as dual Aurora B/FLT3 inhibitors for the treatment of acute myeloid leukemia was written by Jagtap, Ajit Dhananjay;Chang, Pei-Teh;Liu, Jia-Rong;Wang, Hsiao-Chun;Kondekar, Nagendra B.;Shen, Li-Jiuan;Tseng, Hsiang-Wen;Chen, Grace Shiahuy;Chern, Ji-Wang. And the article was included in European Journal of Medicinal Chemistry in 2014.Safety of 3,4-Dichlorobenzamide This article mentions the following:

A series of 6-acylureido derivatives containing a 3-(pyrrol-2-ylmethylidene)indolin-2-one scaffold were synthesized as potential dual Aurora B/FLT3 inhibitors by replacing the 6-arylureido moiety in 6-arylureidoindolin-2-one-based multi-kinase inhibitors. (Z)-N-(2-(pyrrolidin-1-yl)ethyl)-5-((6-(3-(2-fluoro-4-methoxybenzoyl)ureido)-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide I was identified as a dual Aurora B/FLT3 inhibitor (IC₅₀ = 0.4 nM and 0.5 nM, resp.). Compound I also exhibited potent cytotoxicity with single-digit nanomolar IC₅₀ values against the FLT3 mutant-associated human acute myeloid leukemia (AML) cell lines MV4-11 (FLT3-ITD) and MOLM-13 (FLT3-ITD). Compound I also specifically induced extrinsic apoptosis by inhibiting the phosphorylation of the Aurora B and FLT3 pathways in MOLM-13 cells. Compound I had a moderate pharmacokinetic profile. The mesylate salt of I efficiently inhibited tumor growth and reduced the mortality of BALB/c nude mice (s.c. xenograft model) that had been implanted with AML MOLM-13 cells. Compound 54 is more potent than sunitinib not only against FLT3-WT AML cells but also active against sunitinib-resistant FLT3-ITD AML cells. This study demonstrates the significance of dual Aurora B/FLT3 inhibitors for the development of potential agents to treat AML. In the experiment, the researchers used many compounds, for example, 3,4-Dichlorobenzamide (cas: 2670-38-4Safety of 3,4-Dichlorobenzamide).

3,4-Dichlorobenzamide (cas: 2670-38-4) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. Amides can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Safety of 3,4-Dichlorobenzamide

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

Discovery of potent nucleotide pyrophosphatase/phosphodiesterase3 (NPP3) inhibitors with ancillary carbonic anhydrase inhibition for cancer (immuno)therapy was written by Lee, Sang-Yong;Namasivayam, Vigneshwaran;Boshta, Nader M.;Perotti, Arianna;Mirza, Salahuddin;Bua, Silvia;Supuran, Claudiu T.;Mueller, Christa E.. And the article was included in RSC Medicinal Chemistry in 2021.Synthetic Route of C7H10N2O2S This article mentions the following:

Nucleotide pyrophosphatase/phosphodiesterase3 (NPP3) catalyzes the hydrolysis of extracellular nucleotides. It is expressed by immune cells and some carcinomas, e.g. of kidney and colon. Together with ecto-5′-nucleotidase (CD73), NPP3 produces immunosuppressive, cancer-promoting adenosine, and has therefore been proposed as a target for cancer therapy. Here we report on the discovery of 4-[(4-methylphthalazin-1-yl)amino]benzenesulfonamide (1) as an inhibitor of human NPP3 identified by compound library screening. Subsequent structure-activity relationship (SAR) studies led to the potent competitive NPP3 inhibitor 2-methyl-5-{4-[(4-sulfamoylphenyl)amino]phthalazin-1-yl}benzenesulfonamide (23, K_i 53.7 nM vs. the natural substrate ATP). Docking studies predicted its binding pose and interactions. While 23 displayed high selectivity vs. other ecto-nucleotidases, it showed ancillary inhibition of two proposed anti-cancer targets, the carbonic anhydrases CA-II (K_i 74.7 nM) and CA-IX (K_i 20.3 nM). Thus, 23 may act as multi-target anti-cancer drug. SARs for NPP3 were steeper than for CAs leading to the identification of potent dual CA-II/CA-IX (e.g.34) as well as selective CA-IX inhibitors (e.g.31). In the experiment, the researchers used many compounds, for example, 4-Amino-3-methylbenzenesulfonamide (cas: 53297-70-4Synthetic Route of C7H10N2O2S).

4-Amino-3-methylbenzenesulfonamide (cas: 53297-70-4) belongs to amides. The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds. Tertiary amides, with the important exception of N,N-dimethylformamide, exhibit low solubility in water. Ionic, or saltlike, amides are strongly alkaline compounds ordinarily made by treating ammonia, an amine, or a covalent amide with a reactive metal such as sodium.Synthetic Route of C7H10N2O2S

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

Tranilast, a Transient Receptor Potential Vanilloid 2 Channel (TRPV2) Inhibitor Attenuates Amyloid β-Induced Cognitive Impairment: Possible Mechanisms was written by Thapak, Pavan;Bishnoi, Mahendra;Sharma, Shyam Sunder. And the article was included in NeuroMolecular Medicine in 2022.SDS of cas: 53902-12-8 This article mentions the following:

Abstract: Alzheimer’s disease (AD) is associated with the accumulation of β-amyloid and leads to cognitive impairment. Numerous studies have established that neuronal calcium homeostasis is perturbed in AD. Recently, transient receptor potential vanilloid 2 (TRPV2) channels, a non-selective calcium-permeable channel, have been investigated in several diseases. However, the role of the TRPV2 channel has not been investigated in AD yet. In this study, intracerebroventricular administration of β-amyloid (10μg) to Sprague Dawley rats resulted in cognitive impairment which was evident from the assessment of cognitive tests. Also, TRPV2 mRNA and protein expression were found to be upregulated, while the expression of Ca^2+/calmodulin-dependent protein kinase II (p-CaMKII-Thr-286), glycogen synthase kinase 3β (p-GSK-3β-Ser-9), cAMP response element-binding protein (p-CREB-Ser-133), and postsynaptic d. protein 95 (PSD-95) were downregulated in the hippocampus of β-amyloid-treated animals. Even, β-amyloid-treated animals showed upregulation of mRNA level of calcium buffering proteins (parvalbumin and calsequestrin) and calcineurin A (PPP3CA) in the hippocampus. Acetylcholinesterase activity was also increased in the cortex of β-amyloid-treated animals. Three-week treatment with tranilast showed improvement in the cognitive parameters which was associated with a decrease in TRPV2 expression and AChE activity. Addnl., an increase in the protein expression of p-CaMKII, p-GSK-3β, p-CREB and PSD-95 in the hippocampus was found. Downregulation in the mRNA level of calcium buffering proteins (parvalbumin and calsequestrin) and calcineurin A in the hippocampus was also seen. These results reveal the importance of TRPV2 channels in the β-amyloid-induced cognitive deficits and suggest TRPV2 as a potential target for AD. In the experiment, the researchers used many compounds, for example, 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8SDS of cas: 53902-12-8).

2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8) belongs to amides. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well. Thus amides can participate in hydrogen bonding with water and other protic solvents; the oxygen atom can accept hydrogen bonds from water and the N–H hydrogen atoms can donate H-bonds. The presence of the amide group –C(=O)N– is generally easily established, at least in small molecules. It can be distinguished from nitro and cyano groups in IR spectra. Amides exhibit a moderately intense νCO band near 1650 cm−1. By 1H NMR spectroscopy, CONHR signals occur at low fields. In X-ray crystallography, the C(=O)N center together with the three immediately adjacent atoms characteristically define a plane.SDS of cas: 53902-12-8

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

Anionic ortho-Fries rearrangement, a facile route to arenol-based Mannich bases was written by Assimomytis, Nikos;Sariyannis, Yiannis;Stavropoulos, Georgios;Tsoungas, Petros G.;Varvounis, George;Cordopatis, Paul. And the article was included in Synlett in 2009.Safety of N,N-Diethylsalicylamide This article mentions the following:

Phenol and 1-naphthol-based carbamates undergo the anionic ortho-Fries rearrangement to their corresponding amides. Bulky substitution at position 8 of 1-naphthol-based carbamates makes the rearrangement an exclusive reaction, even at -90°, under a variety of conditions. The amides can be efficiently reduced to the corresponding Mannich bases. A novel route to 7-[(dialkylamino)methyl]-8-hydroxy-1-naphthaldehydes is presented. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Safety of N,N-Diethylsalicylamide).

N,N-Diethylsalicylamide (cas: 19311-91-2) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. Ionic, or saltlike, amides are strongly alkaline compounds ordinarily made by treating ammonia, an amine, or a covalent amide with a reactive metal such as sodium.Safety of N,N-Diethylsalicylamide

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

Conformationally locked cis-1,2-diaminocyclohexane-based chiral ligands for asymmetric catalysis was written by van Beek, Carim;Samoshin, Vyacheslav V.. And the article was included in Tetrahedron Letters in 2022.SDS of cas: 2387-23-7 This article mentions the following:

An efficient synthesis for a new conformationally locked chiral cis-1,2-diaminocyclohexane scaffold was developed. The conformational lock allows for convenient sym. derivatization of the amino groups through the reductive amination strategy. A series of optically pure chiral ligands I [R = Bn, 2-HOC₆H₄CH₂, 2-MeOC₆H₄CH₂] based on the cis-DACH scaffold was generated to demonstrate a proof-of-concept for these ligands as chiral catalysts in the asym. Henry reaction. Excellent yields with moderate enantioselectivity were demonstrated at room temperature, with an increase in enantioselectivity at lower temperatures, showing the potential of this new type of cis-DACH ligand. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7SDS of cas: 2387-23-7).

1,3-Dicyclohexylurea (cas: 2387-23-7) belongs to amides. Compared to amines, amides are very weak bases and do not have clearly defined acid–base properties in water. On the other hand, amides are much stronger bases than esters, aldehydes, and ketones. Amides are stable compounds. The lower-melting members (such as acetamide) can be readily purified by fractional distillation. Most amides are solids which have low solubilities in water.SDS of cas: 2387-23-7

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

Selective Transformations of Carbonyl Functions in the Presence of α,β-Unsaturated Ketones: Concise Asymmetric Total Synthesis of Decytospolides A and B was written by Yahata, Kenzo;Minami, Masaki;Watanabe, Kei;Fujioka, Hiromichi. And the article was included in Organic Letters in 2014.Related Products of 192436-83-2 This article mentions the following:

Enones selectively react with a combination of PPh₃ and TMSOTf to produce phosphonium silyl enol ethers, which work as protective groups of enones during the reduction of other carbonyl functions and can be easily deprotected to regenerate parent enones at workup. Thus, enone PhCH:CHCOMe reacted with 3-decanone in the presence of PPh₃/TMSOTf followed by DIBAL-H reduction and K₂CO₃/MeOH to give 3-decanol in 96% yield. Treating keto-enones such as 4-MeCOC₆H₄CH:CHCOMe to the same reaction conditions gave the corresponding selectively reduced product, e.g., 4-MeCH(OH)C₆H₄CH:CHCOMe in 82% yield. Furthermore, the first ketone selective alkylations in the presence of enones were also accomplished. This in situ protection method was applied to concise asym. total syntheses of decytospolides A and B I (R = H, COMe, resp.). In the experiment, the researchers used many compounds, for example, 4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2Related Products of 192436-83-2).

4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2) belongs to amides. Compared to amines, amides are very weak bases and do not have clearly defined acid–base properties in water. On the other hand, amides are much stronger bases than esters, aldehydes, and ketones. Amides can be recrystallised from large quantities of water, ethanol, ethanol/ether, aqueous ethanol, chloroform/toluene, chloroform or acetic acid. The likely impurities are the parent acids or the alkyl esters from which they have been made. The former can be removed by thorough washing with aqueous ammonia followed by recrystallisation, whereas elimination of the latter is by trituration or recrystallisation from an organic solvent.Related Products of 192436-83-2

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