Category: amides-buliding-blocks

Novel steroid derivatives: synthesis, antileishmanial activity, mechanism of action, and in silico physicochemical and pharmacokinetics studies was written by da Trindade Granato, Juliana;dos Santos, Juliana Alves;Calixto, Stephane Lima;Prado da Silva, Natalia;da Silva Martins, Jefferson;da Silva, Adilson David;Coimbra, Elaine Soares. And the article was included in Biomedicine & Pharmacotherapy in 2018.Related Products of 2387-23-7 This article mentions the following:

We investigated the antileishmanial activity and cytotoxicity of novel steroids against murine macrophages with a focus on the derivatives of cholesterol (CD), cholic acid (CA), and deoxycholic acid (DA). Furthermore, the mechanism of action of the best compound was assessed, and in silico studies to evaluate the physicochem. and pharmacokinetic properties were also conducted. Among the sixteen derivatives, schiffbase2, CD2 and DOCAD were effective against promastigotes of Leishmania species. Despite their low toxicity to macrophages, the majority of DOCADs were active against intracellular amastigotes of L. amazonensis, and DOCAD5 exhibited the best biol. effect against these parasitic stages (IC50 = 15.34 μM). Neither the CA derivatives (CAD) nor DA alone inhibited the intracellular parasites. Thus, the absence of hydroxyl in the C-7 position of the steroid nucleus, as well as the modification of the acid group in DOCADs were considered important for antileishmanial activity. The treatment of L. amazonensis promastigote forms with DOCAD5 induced biochem. changes such as depolarization of the mitochondrial membrane potential, increased ROS production and cell cycle arrest. No alterations in parasite plasma membrane integrity were observed In silico physicochem. and pharmacokinetic studies suggest that DOCAD5 could be a good candidate for an oral drug. The data demonstrate the potential antileishmanial effect of certain steroid derivatives and encourage new in vivo studies. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Related Products of 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. As a result of interactions such as these, the water solubility of amides is greater than that of corresponding hydrocarbons. These hydrogen bonds are also have an important role in the secondary structure of proteins.Related Products of 2387-23-7

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

Chlorine Derivatives of Pyridine. Part IX. Preparation and Orientation of 3,5-Dichloropyridine was written by Sell, W. J.. And the article was included in Journal of the Chemical Society, Transactions in 1908.COA of Formula: C6H4Cl2N2O This article mentions the following:

The well-known basic character of this substance suggests that the Cl atoms occupy the 3,5-positions. It is also analogous to dibromopyridine which has been proved to hold Br in the 3,5-positions. Specimens of each were converted into diethoxypyridines and the two proved to be identical. In the experiment, the researchers used many compounds, for example, 3,5-Dichloropicolinamide (cas: 5468-71-3COA of Formula: C6H4Cl2N2O).

3,5-Dichloropicolinamide (cas: 5468-71-3) 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. 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.COA of Formula: C6H4Cl2N2O

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

Biological toxicity of fresh and rotten algae on freshwater fish: LC₅₀, organ damage and antioxidant response was written by Gu, Peng;Li, Qi;Zhang, Weizhen;Gao, Yang;Sun, Ke;Zhou, Liang;Zheng, Zheng. And the article was included in Journal of Hazardous Materials in 2021.Application In Synthesis of 1,3-Dicyclohexylurea This article mentions the following:

In recent decades, harmful algal blooms (HABs) induced by eutrophication have caused organisms in freshwater ecosystems to become surrounded by toxic cells and dissolved toxins. In this study, the toxic effects of fresh algae solution (FAS) and rotten algae solution (RAS) were investigated. The results showed that the composition of RAS was predominantly organic acids, ketones, polypeptides, esters, phenols, amino acids and intermediate metabolic products. The safety concentrations (SCs) of FAS to Carassius auratus, Ctenopharyngodon idellus and Hypophthalmichthys molitrix were 1.92 x 1010 cells/L, 1.58 x 1011 cells/L and 1.30 x 1011 cells/L, resp. The SCs of the RAS were significantly lower than those of the FAS (p < 0.05), with the values of 1.25 x 109 cells/L, 8.8 x 109 cells/L and 9.7 x 109 cells/L, for each species, resp. The toxic algae solutions caused congestion inside the gills, intestinal lesions and high infection rates in the tested fish. FAS and RAS exposure also activated the antioxidant defense system and changed the intestinal microbial structure, resulting in the damage to the microbial balance in the body, and eventually the death of the fish. By studying the acute toxicity to fish, the harm of HABs to aquatic organisms can be predicted. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Application In Synthesis of 1,3-Dicyclohexylurea).

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. 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 In Synthesis of 1,3-Dicyclohexylurea

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

Dehydrogenative Synthesis of Carbamates from Formamides and Alcohols Using a Pincer-Supported Iron Catalyst was written by Townsend, Tanya M.;Bernskoetter, Wesley H.;Hazari, Nilay;Mercado, Brandon Q.. And the article was included in ACS Catalysis in 2021.Recommanded Product: 2387-23-7 This article mentions the following:

The pincer-ligated iron complex (^iPrPNP)Fe(H)(CO) [^iPrPNP^– = N(CH₂CH₂PⁱPr₂)₂-] is an active catalyst for the dehydrogenative synthesis of N-alkyl- and N-aryl-substituted carbamates RNHC(O)OR¹ (R = Me, Ph, Bn, etc.; R¹ = Me, Cy, Bn, etc.) from formamides RNHCHO and alcs. R¹OH. The reaction is compatible with industrially relevant N-alkyl formamides, as well as N-aryl formamides, and 1°, 2°, and benzylic alcs. Mechanistic studies indicate that the first step in the reaction is the dehydrogenation of the formamide to a transient isocyanate by (^iPrPNP)Fe(H)(CO). The cyclohexyl isocyanate then reacts with the alc. to generate the carbamate. However, in a competing reaction, the isocyanate such as benzyl isocyanate, cyclohexyl isocyanate undergoes a reversible cycloaddition with (^iPrPNP)Fe(H)(CO) to generate an off-cycle species, which is the resting state in catalysis. Stoichiometric experiments indicate that high temperatures are required in catalysis to facilitate the release of the isocyanate from the cycloaddition product I (R² = Bn, Cy). Several other off-cycle processes that occur in catalysis, such as the 1,2-addition of the formamide or alc. substrate across the Fe-N bond of (^iPrPNP)Fe(H)(CO) were also identified. It has already been demonstrated that the transient isocyanate generated from dehydrogenation of the formamide can be trapped with amines to form ureas and, in principle, the isocyanate could also be trapped with thiols to form thiocarbamates. Competition experiments indicate that trapping of the transient isocyanate with cyclohexanamine to produce 1,3-dicyclohexylurea is faster than trapping with an alc. to produce carbamates and thus ureas can be formed selectively in the presence of alcs. In contrast, thiols such as benzylthiol, cyclohexanethiol bind irreversibly to the iron catalyst through 1,2 addition across the Fe-N bond of (^iPrPNP)Fe(H)(CO), and it is not possible to produce thiocarbamates. Overall, the mechanistic studies provide general guidelines for facilitating dehydrogenative coupling reactions using (^iPrPNP)Fe(H)(CO) and related catalysts. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Recommanded Product: 2387-23-7).

1,3-Dicyclohexylurea (cas: 2387-23-7) 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. 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: 2387-23-7

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

Para-Selective Cu-Catalyzed C-H Aryloxylation of Electron-Rich Arenes and Heteroarenes was written by Sokolovs, Igors;Suna, Edgars. And the article was included in Journal of Organic Chemistry in 2016.Application In Synthesis of N,N-Diethylsalicylamide This article mentions the following:

Cu-catalyzed reaction of phenols with electron-rich arene or heteroarene ligands of unsym. diaryl-λ³-iodanes is a key step in the developed one-pot two-step method for intermol. para-selective C-H aryloxylation of heteroarenes and arenes. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Application In Synthesis of N,N-Diethylsalicylamide).

N,N-Diethylsalicylamide (cas: 19311-91-2) belongs to amides. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. 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.Application In Synthesis of N,N-Diethylsalicylamide

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

Vitamin B12 levels in drug-treated bacterial cells was written by Gajcy, Hanna. And the article was included in Biochemical Pharmacology in 1975.Reference of 7413-34-5 This article mentions the following:

Sulfathiazole Na [144-74-1] (0.05%), amethopterin Na [7413-34-5] (10-4M), and 5-fluorouracil nitrate [57172-36-8] (0.15 mg/ml) partially inhibited the growth of B. megaterium and decreased the vitamin B12 concentrations Similarly, vitamin B12 concentrations and cell growth were decreased at 30 min after treatment with chloramphenicol [56-75-7] (1 μg) or puromycin-2HCl [58-58-2] (2 μg and 4 μg per ml), but then returned to the initial levels. High concentrations of actinomycin D [50-76-0] and chloramphenicol inhibited cell growth but the vitamin B12 content was increased 2-fold. In the experiment, the researchers used many compounds, for example, Sodium (S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioate (cas: 7413-34-5Reference of 7413-34-5).

Sodium (S)-2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioate (cas: 7413-34-5) 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. As a result of interactions such as these, the water solubility of amides is greater than that of corresponding hydrocarbons. These hydrogen bonds are also have an important role in the secondary structure of proteins.Reference of 7413-34-5

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

A multi-target directed ligands strategy for the treatment of Alzheimer′s disease: Dimethyl fumarate plus Tranilast modified Dithiocarbate as AChE inhibitor and Nrf2 activator was written by Guo, Jie;Cheng, Maojun;Liu, Peng;Cao, Duanyuan;Luo, Jinchong;Wan, Yang;Fang, Yuanying;Jin, Yi;Xie, Sai-Sai;Liu, Jing. And the article was included in European Journal of Medicinal Chemistry in 2022.Formula: C18H17NO5 This article mentions the following:

Alzheimer′s disease (AD) possessed intricate pathogenesis. Currently, multi-targeted drugs were considered to have the potential to against AD by simultaneously triggering mols. in functionally complementary pathways. Hence, a series of mols. based on the pharmacophoric features of Di-Me fumarate, Tranilast, and Dithiocarbate were designed and synthesized. These compounds showed significant AChE inhibitory activity in vitro. Among them, compound 4c₂ displayed the mighty inhibitory activity to hAChE (IC₅₀ = 0.053 μM) and held the ability to cross the BBB. Kinetic study and mol. docking pointed out that 4c₂ bound well into the active sites of hAChE, forming steady and sturdy interactions with key residues in hAChE. Addnl., 4c₂ as an Nrf2 activator could promote the nuclear translocation of Nrf2 protein and induce the expressions of Nrf2-dependent enzymes HO-1, NQO1, and GPX4. Moreover, 4c₂ rescued BV-2 cells from H₂O₂-induced injury and inhibited ROS accumulation. For the anti-neuroinflammatory potential of 4c₂, we observed that 4c₂ could lower the levels of pro-inflammatory cytokines (NO, IL-6 and TNF-α) and suppressed the expressions of iNOS and COX-2. In particular, 4c₂ was well tolerated in mice (2500 mg/kg, p.o.) and efficaciously recovered the memory impairment in a Scopolamine-induced mouse model. Overall, these results highlighted that 4c₂ was a promising multi-targeted agent for treating AD. In the experiment, the researchers used many compounds, for example, 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8Formula: C18H17NO5).

2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. 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.Formula: C18H17NO5

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

Development of a Novel Class of Mitochondrial Ubiquinol-Cytochrome c Reductase Binding Protein (UQCRB) Modulators as Promising Antiangiogenic Leads was written by Jung, Hye Jin;Cho, Misun;Kim, Yonghyo;Han, Gyoonhee;Kwon, Ho Jeong. And the article was included in Journal of Medicinal Chemistry in 2014.Recommanded Product: 1146-43-6 This article mentions the following:

Recently, the authors identified a novel therapeutic target and a small mol. for regulating angiogenesis. The study showed that ubiquinol-cytochrome c reductase binding protein (UQCRB) of the mitochondrial complex III plays a crucial role in hypoxia-induced angiogenesis via mitochondrial reactive oxygen species (ROS) mediated signaling. Herein, the authors developed new synthetic small mols. R¹S(O)₂NHR² [R¹ = 4-biphenyl, 2-naphthyl, quinolin-8-yl, 4-tBuC₆H₄; R² = 2-HOC₆H₄, 3-HOC₆H₄, 4-HOC₆H₄, etc.] that specifically bind to UQCRB and regulate its function. To improve the pharmacol. properties of 6-((1-hydroxynaphthalen-4-ylamino)dioxysulfone)-2H-naphtho[1,8-bc]thiophen-2-one (HDNT), a small mol. that targets UQCRB, a series of HDNT derivatives R¹S(O)₂NHR² were designed and synthesized. Several derivatives showed a significant increase in hypoxia inducible factor 1α (HIF-1α) inhibitory potency compared to HDNT. The compounds bound to UQCRB and suppressed mitochondrial ROS-mediated hypoxic signaling, resulting in potent inhibition of angiogenesis without inducing cytotoxicity. Notably, one of these new derivatives significantly suppressed tumor growth in a mouse xenograft model. Therefore, these mitochondrial UQCRB modulators could be potential leads for the development of novel antiangiogenic agents. In the experiment, the researchers used many compounds, for example, N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6Recommanded Product: 1146-43-6).

N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. 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: 1146-43-6

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

C(sp²)-H Borylation of fluorinated arenes using an air-stable cobalt precatalyst: electronically enhanced site selectivity enables synthetic opportunities was written by Obligacion, Jennifer V.;Bezdek, Mate J.;Chirik, Paul J.. And the article was included in Journal of the American Chemical Society in 2017.HPLC of Formula: 383-31-3 This article mentions the following:

Cobalt(II) carboxylate complexes with pincer pyridinediphosphine tridentate ligands (^RPNP) catalyze ortho-directed C-H-borylation of aryl fluorides with electronically enhanced site selectivity, as evidenced by the high ortho-to-fluorine selectivity observed in the C(sp²)-H borylation of fluorinated arenes. Both the air-sensitive cobalt(III) dihydride boryl [[4-Me-2,6-(ⁱPr₂PCH₂)₂py]CoH₂BPin] (1) and the air-stable cobalt(II) bis(pivalate) [[4-Me-2,6-(ⁱPr₂PCH₂)₂py]Co(O₂C^tBu)₂] (2) compounds were effective and exhibited broad functional group tolerance across a wide range of fluoroarenes containing electronically diverse functional groups, regardless of the substitution pattern on the arene. The electronically enhanced ortho-to-fluorine selectivity observed with the cobalt catalysts was maintained in the presence of a benzylic dimethylamine and hydrosilanes, overriding the established directing-group effects observed with precious-metal catalysts. The synthetically useful selectivity observed with cobalt was applied to an efficient synthesis of the anti-inflammatory drug flurbiprofen. In the experiment, the researchers used many compounds, for example, 4-Fluoro-N,N-dimethylbenzenesulfonamide (cas: 383-31-3HPLC of Formula: 383-31-3).

4-Fluoro-N,N-dimethylbenzenesulfonamide (cas: 383-31-3) 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. 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.HPLC of Formula: 383-31-3

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

Oxidative metabolism of N-isopropyl-α-(2-methylazo)-p-toluamide (azoprocarbazine) by rodent liver microsomes was written by Wiebkin, Philip;Prough, Russell A.. And the article was included in Cancer Research in 1980.Safety of 4-Formyl-N-isopropylbenzamide This article mentions the following:

Azoprocarbazine (I) [2235-59-8] is oxidized by rat liver microsomes in the presence of NADPH and O to yield 2 major metabolites as determined by high-pressure liquid chromatog. The isolated products are the 2 isomeric azoxy derivatives, N-isopropyl-α-(2-methyl-NNO-azoxy)-p-toluamide (benzylazoxy) [66944-55-6] and N-isopropyl-α-(2-methyl-ONN-azoxy)-p-toluamide (methylazoxy) [66944-56-7], since the mass spectra of the metabolites are distinctly different from each other but are identical to those of the resp. chem. synthesized azoxy standards In addition, p-formyl-N-isopropylbenzamide [13255-50-0] is also formed in measurable quantities. Liver microsomes from untreated rabbits or rats form only the methylazoxy derivative; the benzylazoxy isomer is nearly undetectable. Animal pretreatment with phenobarbital or 5,6-benzoflavone results in a marked increase in the rate of methylazoxy formation catalyzed by rat or rabbit liver microsomes. The rate of benzylazoxy formation is also stimulated by phenobarbital pretreatment but is unaffected by 5,6-benzoflavone pretreatment. The rate of formation of p-formyl-N-isopropylbenzamide as well is increased by animal pretreatment with either 5,6-benzoflavone or phenobarbital. Kinetic evaluation of these data suggests the possible involvement of >1 species of cytochrome P-450 in these reactions. Production of both benzylazoxy- and methylazoxyprocarbazine by rat liver microsomes is inhibited by a number of specific cytochrome P-420 inhibitors. Azoprocarbazine elicits a very weak spectral complex (type II) with rat liver microsomal cytochrome P-450 [9035-51-2]. These results strongly suggest that cytochrome P-450 dependent monooxygenases are involved in the N-oxidation of azoprocarbazine to yield 2 azoxy isomers of procarbazine. Incubation of liver microsomal protein with [¹⁴C]azoprocarbazine, O, and NADPH results in a time-dependent increase in covalent binding of labeled material to microsomal protein. More protein-bound label is obtained with [Me-¹⁴C]-azoprocarbazine than with [ring-¹⁴C]azoprocarbazine, suggesting that the mol. can be metabolically activated to a moiety which preferentially binds the Me portion of its structure to microsomal protein in vitro. In the experiment, the researchers used many compounds, for example, 4-Formyl-N-isopropylbenzamide (cas: 13255-50-0Safety of 4-Formyl-N-isopropylbenzamide).

4-Formyl-N-isopropylbenzamide (cas: 13255-50-0) 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. As a result of interactions such as these, the water solubility of amides is greater than that of corresponding hydrocarbons. These hydrogen bonds are also have an important role in the secondary structure of proteins.Safety of 4-Formyl-N-isopropylbenzamide

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