Month: October 2022

《Stabilizing p-Dithiobenzyl Urethane Linkers without Rate-Limiting Self-Immolation for Traceless Drug Release》 was published in ChemMedChem in 2019. These research results belong to Zheng, Yiwu; Shen, Yang; Meng, Xiaoting; Wu, Yaqi; Zhao, Yibing; Wu, Chuanliu. Category: amides-buliding-blocks The article mentions the following:

Exploiting the redox sensitivity of disulfide bonds is a prevalent strategy in targeted prodrug designs. In contrast to aliphatic disulfides, p-thiobenzyl-based disulfides have rarely been used for prodrug designs, given their intrinsic instability caused by the low pKa of aromatic thiols. Here, we examined the interplay between steric hindrance and the low-pKa effect on thiol-disulfide exchange reactions and uncovered a new thiol-disulfide exchange process for the self-immolation of p-thiobenzyl-based disulfides. We observed a central leaving group shifting effect in the α,α-dimethyl-substituted p-dithiobenzyl urethane linkers (DMTB linkers), which leads to increased disulfide stability by more than two orders of magnitude, an extent that is significantly greater than that observed with typical aliphatic disulfides. In particular, the DMTB linkers display not only high stability, but also rapid self-immolation kinetics due to the low pKa of the aromatic thiol, which can be used as a general and robust linkage between targeting reagents and cytotoxic drugs for targeted prodrug designs. The unique and promising stability characteristics of the present DMTB linker will likely inspire the development of novel targeted prodrugs to achieve traceless release of drugs into cells. In the experiment, the researchers used H-Lys(Boc)-OH(cas: 2418-95-3Category: amides-buliding-blocks)

H-Lys(Boc)-OH(cas: 2418-95-3) belongs to amino acids. Amino acids are not generally considered to be electrochemically active because products of the oxidation accumulate on the electrode surface and prevent it from participating in any further electrochemical processes.Category: amides-buliding-blocks

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

Recommanded Product: H-Lys(Boc)-OHOn October 8, 2019 ,《Stable, Bioresponsive, and Macrophage-Evading Polyurethane Micelles Containing an Anionic Tripeptide Chain Extender》 was published in ACS Omega. The article was written by Fang, Danxuan; Pi, Menghan; Pan, Zhicheng; Song, Nijia; He, Xueling; Li, Jiehua; Luo, Feng; Tan, Hong; Li, Zhen. The article contains the following contents:

Polymeric nanocarriers have been extensively used in medicinal applications for drug delivery. However, i.v. nanocarriers circulating in the blood will be rapidly cleared from the mononuclear macrophage system. The surface physicochem. characterizations of nanocarriers are the primary factors to determine their fate in vivo, such as evading the reticuloendothelial system, exhibiting long blood circulation times, and accumulating in the targeted site. In this work, we develop a series of polyurethane micelles containing segments of an anionic tripeptide, hydrophilic mPEG, and disulfide bonds. It is found that the long hydrophilic mPEG can shield the micellar surface and have a synergistic effect with the neg. charged tripeptide to minimize macrophage phagocytosis. Meanwhile, the disulfide bond can rapidly respond to the intracellular reduction environment, leading to the acceleration of drug release and improvement of the therapeutic effect. Our results verify that these anionic polyurethane micelles hold great potential in the development of the stealth immune system and controllable intracellular drug transporters. In the experimental materials used by the author, we found H-Lys(Boc)-OH(cas: 2418-95-3Recommanded Product: H-Lys(Boc)-OH)

H-Lys(Boc)-OH(cas: 2418-95-3) belongs to amino acids. Amino acids are not generally considered to be electrochemically active because products of the oxidation accumulate on the electrode surface and prevent it from participating in any further electrochemical processes.Recommanded Product: H-Lys(Boc)-OH

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

Name: 2-Hydroxy-N-phenylacetamideOn September 23, 2015 ,《Vilsmeier reagent initialed sequential one-pot multicomponent synthesis of N,O-disubstituted glycolamides as dipeptidyl peptidase 4 inhibitors》 was published in Tetrahedron. The article was written by Lu, Shi-Han; Yen, Wan-Ping; Tsai, Henry J.; Chen, Chien-Shu; Wong, Fung Fuh. The article contains the following contents:

A series of N,O-disubstituted glycolamide derivatives have been successfully synthesized through Vilsmeier reagent initialed sequential one-pot multicomponent procedure from α-chloro N-arylacetamides with formamide/PBr3 and acid chloride. The three-step synthesis involved Vilsmeier formyloxylation reaction, decarbonylation, and esterification. The strategy was also applicable to α-chloro N-(naphthalenyl)acetamide to prepare the corresponding N,O-disubstituted glycolamide products. All of N,O-disubstituted glycolamides were evaluated against dipeptidyl peptidase 4 inhibitory activity. Based on the inhibitory results, several of O-furan-2-carbonyl and O-quinoline-8-sulfonyl N-aryl glycolamide compounds possessed the better effective inhibition of dipeptidyl peptidase 4. The experimental part of the paper was very detailed, including the reaction process of 2-Hydroxy-N-phenylacetamide(cas: 4746-61-6Name: 2-Hydroxy-N-phenylacetamide)

2-Hydroxy-N-phenylacetamide(cas: 4746-61-6) 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.“,” In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well. Name: 2-Hydroxy-N-phenylacetamide

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

Safety of N-(Pyridin-4-yl)isonicotinamideOn October 7, 2011 ,《Ligand-concentration-dependent self-organization of Hoffman- and PtS-type frameworks from one-pot crystallization》 was published in CrystEngComm. The article was written by Chen, Xin; Zhou, Hu; Chen, Ying-Ying; Yuan, Ai-Hua. The article contains the following contents:

Hoffman- and PtS-type frameworks [ZnL][Ni(CN)4].3H2O (1), ZnNi(CN)4 (2) and ZnNi(CN)4.2CH3CN (3) (L = N-(4-pyridyl)isonicotinamide) were isolated from 1-pot crystallization and characterized structurally. A ligand-concentration effect is proposed in such a self-organized system. In the experimental materials used by the author, we found N-(Pyridin-4-yl)isonicotinamide(cas: 64479-78-3Safety of N-(Pyridin-4-yl)isonicotinamide)

N-(Pyridin-4-yl)isonicotinamide(cas: 64479-78-3) belongs to amides.Safety of N-(Pyridin-4-yl)isonicotinamideAmides 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.

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

The author of 《A facile approach to trans-4,5-pyrrolidine lactam and application in the synthesis of nemonapride and streptopyrrolidine》 were Huang, Wei; Ma, Jing-Yi; Yuan, Mu; Xu, Long-Fei; Wei, Bang-Guo. And the article was published in Tetrahedron in 2011. HPLC of Formula: 87694-50-6 The author mentioned the following in the article:

An efficient approach to trans-4-hydroxylpyrrolidine lactams, e.g. I [R1 = t-Bu, PhCH2; R2 = H, Me; Me2CH, etc.; R3 = H, TBSO], starting from an amino acid is described. The utility of this method has been demonstrated in the synthesis of antipsychotic nemonapride and antiangiogenic streptopyrrolidine. The results came from multiple reactions, including the reaction of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6HPLC of Formula: 87694-50-6)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides.HPLC of Formula: 87694-50-6 Amides include many other important biological compounds, as well as many drugs like paracetamol, penicillin and LSD. Low-molecular-weight amides, such as dimethylformamide, are common solvents.

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

The author of 《Dynamic porous metal-organic frameworks: synthesis, structure and sorption property》 were Hou, Chao; Liu, Qing; Okamura, Taka-aki; Wang, Peng; Sun, Wei-Yin. And the article was published in CrystEngComm in 2012. Recommanded Product: N-(Pyridin-4-yl)isonicotinamide The author mentioned the following in the article:

Three new porous metal-organic frameworks {[Co(L)(PIN)]·dioxane·H2O}n (1), {[Co(L)(DPE)]·0.5DPE}n (2) and {[Co(L)(BPE)]·4H2O}n (3) with the same 2-fold interpenetrating hms topol. based on 5-(pyridin-4-yl)isophthalate (L2-) and different pillar ligands of N-(4-pyridyl)isonicotinamide (PIN), 1,2-di(4-pyridyl)ethylene (DPE) and 1,2-bis(4-pyridyl)ethane (BPE) were prepared and characterized by IR, TGA, single crystal and powder x-ray diffractions. 1 Possesses a flexible framework upon desolvation and H2O/MeOH/EtOH vapor adsorption, and the desolvated sample exhibits a stepwise uptake of CO2 (195 K), H2O (298 K) and MeOH (298 K). More importantly, the desolvated 1 shows high enthalpy of CO2 adsorption and high selectivity for CO2 over N2 as well as H2O/MeOH over EtOH at 298 K. In the experimental materials used by the author, we found N-(Pyridin-4-yl)isonicotinamide(cas: 64479-78-3Recommanded Product: N-(Pyridin-4-yl)isonicotinamide)

N-(Pyridin-4-yl)isonicotinamide(cas: 64479-78-3) belongs to amides.Recommanded Product: N-(Pyridin-4-yl)isonicotinamide Amides include many other important biological compounds, as well as many drugs like paracetamol, penicillin and LSD. Low-molecular-weight amides, such as dimethylformamide, are common solvents.

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

The author of 《Enantioselective Construction of Chiral Sulfides via Catalytic Electrophilic Azidothiolation and Oxythiolation of N-Allyl Sulfonamides》 were Liang, Yaoyu; Zhao, Xiaodan. And the article was published in ACS Catalysis in 2019. Reference of 4-Methylbenzenesulfonamide The author mentioned the following in the article:

An efficient and convenient pathway was developed for enantioselective synthesis of chiral sulfides by chiral bifunctional selenide-catalyzed electrophilic azidothiolation and oxythiolation of N-allyl sulfonamides. By this protocol, a variety of chiral vicinal azidosulfides and oxysulfides were obtained in good yields with high enantioselectivities and diastereoselectivities. In this transformation, not only electrophilic arylthiolating reagents but also a wide range of electrophilic alkylthiolating reagents worked very well. The practical application of this method was elucidated by further transformations of the products into the diversified compounds The results came from multiple reactions, including the reaction of 4-Methylbenzenesulfonamide(cas: 70-55-3Reference of 4-Methylbenzenesulfonamide)

4-Methylbenzenesulfonamide(cas: 70-55-3) belongs to anime. Amines can be classified according to the nature and number of substituents on nitrogen. Aliphatic amines contain only H and alkyl substituents. Aromatic amines have the nitrogen atom connected to an aromatic ring.Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine (NClH2).Reference of 4-Methylbenzenesulfonamide

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

The author of 《Rhodium(III)-Catalyzed Oxidative Annulation of Ketoximes with Sulfonamide: A Direct Approach to Indazoles》 were Wang, Ning; Liu, Lingling; Xu, Wentao; Zhang, Mengye; Huang, Zhibin; Shi, Daqing; Zhao, Yingsheng. And the article was published in Organic Letters in 2019. Synthetic Route of C7H9NO2S The author mentioned the following in the article:

A rhodium(III)-catalyzed intermol. C-H amination of ketoxime and iodobenzene diacetate-enabled N-N bond formation in the synthesis of indazoles has been developed. A variety of functional groups were well tolerated, providing the corresponding products in moderate to good yields. Moreover, the nitro-substituted ketoximes are well compatible in this reaction, leading to the corresponding products in moderate to good yields.4-Methylbenzenesulfonamide(cas: 70-55-3Synthetic Route of C7H9NO2S) was used in this study.

4-Methylbenzenesulfonamide(cas: 70-55-3) belongs to anime. Reduction of nitro compounds, RNO2, by hydrogen or other reducing agents produces primary amines cleanly (i.e., without a mixture of products), but the method is mostly used for aromatic amines because of the limited availability of aliphatic nitro compounds. Reduction of nitriles and oximes (R2C=NOH) also yields primary amines.Synthetic Route of C7H9NO2S

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

El-Zahraa, F.; El-Basil, S.; El-Sayed, M.; Ghoneim, K. M.; Khalifa, M. published an article on January 31 ,1979. The article was titled 《Synthesis and pharmacological screening of certain N-substituted amides structurally related to some local anesthetics》, and you may find the article in Pharmazie.HPLC of Formula: 70298-88-3 The information in the text is summarized as follows:

Eighteen Ph2CHCONHR (I; R = e.g., 2,6-, 2,5-, 2,4-, 3,4-, 3,5-Me2C6H3, 4,5-MeClC6H3, 4-O2NC6H4) and 14 Me3CCONHR1 (II; R1 = e.g., 3,6-Me2C6H3, 3-pyridyl, 4-nitro-2-pyridyl) were prepared in 45-90% yield by reaction of the acid chloride with the resp. amine. The most active intradermal anesthesia in guinea pigs was I (R = 4-methyl-5-chlorophenyl); its activity was more than double that of procaine hydrochloride. As a corneal anesthetic II (R1 = 2,6-Me2C6H3) was the most active anesthetic and for plexus anesthesia I (R = 2,6-Me2C6H3) was the most active. In the experimental materials used by the author, we found 2,2-Dimehtyl-N-pyridin-3-yl-propionamide(cas: 70298-88-3HPLC of Formula: 70298-88-3)

2,2-Dimehtyl-N-pyridin-3-yl-propionamide(cas: 70298-88-3) belongs to anime. Amines have a free lone pair with which they can coordinate to metal centers. Amine–metal bonds are weaker because amines are incapable of backbonding, but they are still important for sensing applications.While stronger than hydrogen bonds, amine–metal bonds are still weaker than both covalent and ionic bonds.HPLC of Formula: 70298-88-3

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

The author of 《Metabolism of N-acylated and O-alkylated drugs by intestinal microflora during anaerobic incubation in vitro》 were Smith, G. E.; Griffiths, L. A.. And the article was published in Xenobiotica in 1974. COA of Formula: C8H9NO2 The author mentioned the following in the article:

Phenacetin [62-44-2] and derivatives of acetanilide were N-deacylated by rat cecal microflora, the deacylation of the latter being dependent on the nature and position of the substituents. Thus, p-alkylated or o-, m-, or p-hydroxylated derivatives were deacylated, whereas a p-aromatic or halide substituent or an aromatic acyl grouping prevented deacylation. A few O-alkylated compounds with a simple benzenoid structure were dealkylated by cecal microflora, but none of the N-alkylated drugs were dealkylated. In the experiment, the researchers used many compounds, for example, 2-Hydroxy-N-phenylacetamide(cas: 4746-61-6COA of Formula: C8H9NO2)

2-Hydroxy-N-phenylacetamide(cas: 4746-61-6) belongs to amides. Amides include many other important biological compounds, as well as many drugs like paracetamol, penicillin and LSD. Low-molecular-weight amides, such as dimethylformamide, are common solvents.COA of Formula: C8H9NO2

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