Month: December 2022

Ouyang, Jinbo published the artcileCocrystal design of vanillin with amide drugs: Crystal structure determination, solubility enhancement, DFT calculation, Recommanded Product: Isonicotinamide, the publication is Chemical Engineering Research and Design (2022), 170-180, database is CAplus.

Vanillin (VAN) is widely used in medicine, food and optoelectronics, but its low solubility leads to the decrease of bioavailability and increase of application costs. Three APIs-nicotinamide (NIC), isonicotinamide (INM) and isoniazid (INH) were chosen to form cocrystals with VAN, aiming at improving the solubility of VAN and APIs simultaneously. Two cocrystals (VAN-NIC, VAN-INM) were obtained through cocrystn. while VAN reacted with INH to form one novel compound (VAN-INH). The crystal structures were characterized by single-crystal X-ray diffraction (SCXRD), Powder X-ray diffraction (PXRD), Fourier-Transform IR Spectroscopy (FT-IR) and Differential Scanning Calorimetry (DSC). The melting temperatures of VAN-NIC and VAN-INM cocrystals are between this of VAN and APIs. Compared with pure VAN and APIs, the solubility and dissolution rate of VAN-NIC and VAN-INM are significantly increased. The melting temperature of VAN-INH is greater than that of VAN and INH, and the solubility and dissolution rate is not increased significantly. The intermol. energy between VAN and APIs as well as lattice energies of cocrystals/novel compound were computed to elucidate the formation mechanism and stability. The present investigation opens a new pathway for the development of natural product-drug cocrystals to improve solubility and dissolution rate of natural product.

Chemical Engineering Research and Design published new progress about 1453-82-3. 1453-82-3 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is Isonicotinamide, and the molecular formula is C6H6N2O, Recommanded Product: Isonicotinamide.

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

Wang, Xiao-Meng published the artcileSynthesis and antitumor activities evaluation of m-(4-morpholinoquinazolin-2-yl)benzamides in vitro and in vivo, Application of N-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide, the publication is European Journal of Medicinal Chemistry (2015), 382-395, database is CAplus and MEDLINE.

In the present study, a series of m-(4-morpholinoquinazolin-2-yl)benzamides were designed, synthesized, and characterized. The antiproliferative activities of the synthesized compounds were evaluated against two human cell lines (HCT-116 and MCF-7). Compounds with IC₅₀ values below 4 μM were further evaluated against U-87 MG and A549 cell lines. Among these evaluated compounds, compound I displayed a remarkable antiproliferative effect in vitro. The hoechst staining assay showed that compound I caused morphol. changes. The cell cycle and apoptosis assay further indicated that compound I can arrest HCT-116 cells in G2/M and G0/G1 phase and induce apoptosis. PI3K enzyme assays indicated that compounds I and II selectively inhibit PI3Kα. A Western bolt assay further suggested that compound I can block the PI3K/Akt/mTOR pathway. Moreover, compound I inhibited tumor growth on a mice S180 homograft model. These findings directly identify m-(4-morpholinoquinazolin-2-yl)benzamide derivatives as novel anticancer agents.

European Journal of Medicinal Chemistry published new progress about 1197171-76-8. 1197171-76-8 belongs to amides-buliding-blocks, auxiliary class Boronic acid and ester,Amine,Benzene,Amide,Boronate Esters,Boronic Acids,Boronic acid and ester,, name is N-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide, and the molecular formula is C18H28B2O4, Application of N-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide.

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

Cao, Yu published the artcileSynthesis and activity on bis-ureas of thiadiazole, Computed Properties of 2447-79-2, the publication is Huaxue Shiji (2012), 34(11), 982-984,998, database is CAplus.

Seven new bis-ureas of thiadiazloe derived from 2-amino-5-mercapto-1,3,4-thiadiazole, 1,3-dibromopropane and acyl azides were synthesized and characterized by the phys. constants, elementary anal., IR, and ¹HNMR. The optimal conditions for preparation of bis-ureas of thiadiazloe were as follows: n(bis-ureas of thiadiazloe): n was 1.0:1.0, and the reaction time was 4 h at 40 °C, The product yield of bis-ureas of thiadiazloe could reach 63.5%. The results of biol. activity tests showed that all samples have activity on plant growth hormone and auxin.

Huaxue Shiji published new progress about 2447-79-2. 2447-79-2 belongs to amides-buliding-blocks, auxiliary class Chloride,Amine,Benzene,Amide, name is 2,4-Dichlorobenzamide, and the molecular formula is C7H5Cl2NO, Computed Properties of 2447-79-2.

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

Huang, Wei published the artcileCytosolic p53 inhibits Parkin- mediated mitophagy and promotes acute liver injury induced by heat stroke, Category: amides-buliding-blocks, the publication is Frontiers in Immunology (2022), 859231, database is CAplus and MEDLINE.

Heat stroke (HS) is a severe condition characterized by increased morbidity and high mortality. Acute liver injury (ALI) is a well-documented complication of HS. The tumor suppressor p53 plays an important role in regulation of mitochondrial integrity and mitophagy in several forms of ALI. However, the role of p53-regulated mitophagy in HS-ALI remains unclear. In our study, we discovered the dynamic changes of mitophagy in hepatocytes and demonstrated the protective effects of mitophagy activation on HS-ALI. Pretreatment with 3-MA or Mdivi-1 significantly exacerbated ALI by inhibiting mitophagy in HS-ALI mice. Consistent with the animal HS-ALI model results, silencing Parkin aggravated mitochondrial damage and apoptosis by inhibiting mitophagy in HS-treated normal human liver cell line (LO2 cells). Moreover, we described an increase in the translocation of p53 from the nucleus to the cytoplasm, and cytosolic p53 binds to Parkin in LO2 cells following HS. p53 overexpression using a specific adenovirus or Tenovin-6 exacerbated HS-ALI through Parkin-dependent mitophagy both in vivo and in vitro, whereas inhibition of p53 using siRNA or PFT- α effectively reversed this process. Our results demonstrate that cytosolic p53 binds to Parkin and inhibits mitophagy by preventing Parkin’s translocation from the cytosol to the mitochondria, which decreases mitophagy activation and leads to hepatocyte apoptosis in HS-ALI. Overall, pharmacol. induction of mitophagy by inhibiting p53 may be a promising therapeutic approach for HS-ALI treatment.

Frontiers in Immunology published new progress about 1011557-82-6. 1011557-82-6 belongs to amides-buliding-blocks, auxiliary class Epigenetics,Sirtuin, name is 4-(tert-Butyl)-N-((4-(5-(dimethylamino)pentanamido)phenyl)carbamothioyl)benzamide, and the molecular formula is C25H34N4O2S, Category: amides-buliding-blocks.

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

Zhuo, Liang published the artcileAerobic Visible-Light Induced Intermolecular S-N Bond Construction: Synthesis of 1,2,4-Thiadiazoles from Thioamides under Photosensitizer-Free Conditions, Safety of 3-Methoxybenzothioamide, the publication is European Journal of Organic Chemistry (2021), 2021(23), 3398-3402, database is CAplus.

Aerobic visible-light induced intermol. S-N bond construction has been achieved without the addition of photosensitizer, metal, or base. With this strategy, 1,2,4-thiadiazoles I (R = Ph, 4-methoxyphenyl, thiophen-3-yl, etc.; R¹ = 4-methoxyphenyl, 2,6-dimethylphenyl, thiophen-2-yl, etc.) can be obtained from thioamides R/R¹C(S)NH₂. Preliminary mechanistic investigation suggested that the excited state of thioamides undergoes a single-electron-transfer (SET) process to afford thioamidyl radicals, which can be further transformed into a 1,2,4-thiadiazole through desulfurization and oxidative cyclization. The reaction has good functional group tolerance and represents a green method for the construction of S-N bonds.

European Journal of Organic Chemistry published new progress about 64559-06-4. 64559-06-4 belongs to amides-buliding-blocks, auxiliary class Amine,Benzene,Amide,Ether, name is 3-Methoxybenzothioamide, and the molecular formula is C15H24O2, Safety of 3-Methoxybenzothioamide.

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

Xu, Shisan published the artcileProlonged neutrophil retention in the wound impairs zebrafish heart regeneration after cryoinjury., Safety of [(2-Hexylcyclopentylidene)amino]thiourea, the publication is Fish & Shellfish Immunology (2019), 447-454, database is CAplus and MEDLINE.

Neutrophils are the first line defenders in the innate immune response, and rapidly migrate to an infected or injured area. Recently, bidirectional migration of neutrophils to the wound and the corresponding functions have become popular research pursuits. In zebrafish larvae, CXCR1/CXCL8 is the predominant chemoattractant pathway to recruit neutrophil to wound, while CXCR2/CXCL8 pathway mediate neutrophil dispersal in wound after injury. Here, we found that both CXCR1/CXCL8 and LTB4/BLT1 signals are activated in zebrafish heart after cryoinjury. And with a CXCR1/2 selective inhibitor (SB225002) treatment, the recruitment of neutrophils was not affected, but reverse migration of neutrophils was inhibited after cryoinjury of heart. We suggested that the neutrophil recruitment to cryoinjured area might be mediated by LTB4/BLT1 signals at the presence of SB225002. Therefore, SB225002 treatment resulted more accumulation and long retention of neutrophils in the injured heart. The long retention of neutrophils in the wound promoted revascularization in the injured heart; however, the AKT/mTOR pathway was inhibited and the regeneration was impaired. Our findings suggest that retention of neutrophils is a well-orchestrated process and might regulate regeneration by the AKT/mTOR pathway.

Fish & Shellfish Immunology published new progress about 321673-30-7. 321673-30-7 belongs to amides-buliding-blocks, auxiliary class Immunology/Inflammation,Scavenger receptor, name is [(2-Hexylcyclopentylidene)amino]thiourea, and the molecular formula is C15H10O2, Safety of [(2-Hexylcyclopentylidene)amino]thiourea.

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

Fang, Lan published the artcileIntermolecular interactions and solubility behavior of multicomponent crystal forms of 2,4-D: design, structure analysis, and solid-state characterization, Product Details of C6H6N2O, the publication is CrystEngComm (2021), 23(43), 7615-7627, database is CAplus.

2,4-Dichlorophenoxyacetic acid (2,4-D) is a kind of plant growth regulator which exhibits hormesis effects at low dosages, while high dosages adversely affect the exposed organisms and act as herbicide. 2,4-D has low solubility, therefore, it is a good candidate for crystal engineering research to improve its solubility This paper presents the preparation of five new multicomponent crystals of 2,4-D, including three salts with imidazole (IMZ), 2-aminopyridine (AAP), and 3-aminopyridine (BAP), and two cocrystals with isonicotinamide (ISO) and pyrazinamide (PYM) as coformers (CCFs). The five multicomponent crystals were first characterized by single-crystal X-ray diffraction, powder X-ray diffraction, differential scanning calorimetry, and thermogravimetric anal. Mol. interactions, crystal packing, and structure similarity analyses performed using Hirshfeld surface and CrystalCMP confirmed the charge-assisted H-bonding sites and structural similarity among the solved crystal structures. The stability tests show that all five multi-component crystals exhibit excellent stability within 12 wk under accelerated storage conditions (40°C and 75% RH). Moreover, all the five multicomponent crystals of 2,4-D exhibit increased solubility, especially (2,4-D)⁺(IMZ)^– that increased the solubility of the resulting salt by 70 times compared to the free acid 2,4-D. From the perspective of single-crystal structure and intermol. interaction, the reasons for these changes in phys. and chem. properties are further clarified.

CrystEngComm published new progress about 1453-82-3. 1453-82-3 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is Isonicotinamide, and the molecular formula is C6H6N2O, Product Details of C6H6N2O.

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

Chen, Jiajia published the artcileTransamidation for the Synthesis of Primary Amides at Room Temperature, HPLC of Formula: 1453-82-3, the publication is Organic Letters (2020), 22(9), 3504-3508, database is CAplus and MEDLINE.

Various primary amides have been synthesized using the transamidation of various tertiary amides under metal-free and mild reaction conditions. When (NH₄)₂CO₃ reacts with a tertiary amide bearing an N-electron-withdrawing substituent, such as sulfonyl and diacyl, in DMSO at 25°C, the desired primary amide product is formed in good yield with good functional group tolerance. In addition, N-tosylated lactam derivatives afforded their corresponding N-tosylamido alkyl amide products via a ring opening reaction.

Organic Letters published new progress about 1453-82-3. 1453-82-3 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is Isonicotinamide, and the molecular formula is C6H6N2O, HPLC of Formula: 1453-82-3.

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

Maddaloni, Ernesto published the artcileHigh density lipoprotein modulates osteocalcin expression in circulating monocytes: a potential protective mechanism for cardiovascular disease in type 1 diabetes, HPLC of Formula: 321673-30-7, the publication is Cardiovascular Diabetology (2017), 116/1-116/11, database is CAplus and MEDLINE.

Background: Cardiovascular disease (CVD) is a major cause of mortality in type 1 diabetes (T1D). A pro-calcific drift of circulating monocytes has been linked to vascular calcification and is marked by the surface expression of osteocalcin (OCN). We studied OCN + monocytes in a unique population with ≥50 years of T1D, the 50-Yr Joslin Medalists (J50M). Methods: CD45 bright/CD14 + /OCN + cells in the circulating mononuclear blood cell fraction were quantified by flow cytometry and reported as percentage of CD45 bright cells. Mechanisms were studied by inducing OCN expression in human monocytes in vitro. Results: Subjects without history of CVD (n = 16) showed lower levels of OCN + monocytes than subjects with CVD (n = 14) (13.1 α 8.4% vs 19.9 α 6.4%, p = 0.02). OCN + monocytes level was inversely related to total high d. lipoprotein (HDL) cholesterol levels (r = -0.424, p = 0.02), large (r = -0.413, p = 0.02) and intermediate (r = -0.445, p = 0.01) HDL sub-fractions, but not to small HDL. In vitro, incubation with OxLDL significantly increased the number of OCN + monocytes (p < 0.01). This action of OxLDL was significantly reduced by the addition of HDL in a concentration dependent manner (p < 0.001). Inhibition of the scavenger receptor B1 reduced the effects of both OxLDL and HDL (p < 0.05). Conclusions: Low OCN + monocytes levels are associated with lack of CVD in people with long duration T1D. A possible mechanism for the increased OCN + monocytes could be the elevated levels of oxidized lipids due to diabetes which may be inhibited by HDL. These findings suggest that circulating OCN + monocytes could be a marker for vascular disease in diabetic patients and possibly modified by HDL elevation.

Cardiovascular Diabetology published new progress about 321673-30-7. 321673-30-7 belongs to amides-buliding-blocks, auxiliary class Immunology/Inflammation,Scavenger receptor, name is [(2-Hexylcyclopentylidene)amino]thiourea, and the molecular formula is C12H23N3S, HPLC of Formula: 321673-30-7.

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

Shim, Min Suk published the artcileA Reactive Oxygen Species (ROS)-Responsive Polymer for Safe, Efficient, and Targeted Gene Delivery in Cancer Cells, Synthetic Route of 1869-45-0, the publication is Angewandte Chemie, International Edition (2013), 52(27), 6926-6929, database is CAplus and MEDLINE.

Thioketal-based I was prepared for targeted gene delivery in prostate cancer. Degradation of thioketal linkages in I under reactive oxygen species conditions led to efficient intracellular release of the complexed DNA in prostate cancer cells. The DNA-I polyplexes exhibited efficient gene transfection. Incorporation of GRP78-binding peptide into I achieved cancer-targeted gene transfection.

Angewandte Chemie, International Edition published new progress about 1869-45-0. 1869-45-0 belongs to amides-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is 2,2,2-Trifluoro-N-(2-mercaptoethyl)acetamide, and the molecular formula is C10H14N2O, Synthetic Route of 1869-45-0.

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