Tag: M.W=150-200

Lee, Jinho published the artcile3,5-Bis(aminopyrimidinyl)indole Derivatives: Synthesis and Evaluation of Pim Kinase Inhibitory Activities, Quality Control of 56-05-3, the publication is Bulletin of the Korean Chemical Society (2014), 35(7), 2123-2129, database is CAplus.

A novel series of 3,5-bis(aminopyrimidinyl)indole derivatives I (R = (CH₃)₂N(CH₂)₂O, cyclopentyloxy, Me piperazinyl, etc.) were synthesized and evaluated against Pim kinases, meridianin C was chosen as a hit structure and its substituent was modified to discover potent and selective pan-pim kinase inhibitors. Substitution at C-5-position by 2-amino-pyrimidine having hydrophilic aminoalkyl chain improved the potency were described. SAR o f substituents at C-4 position of 2-amino-pyrimidine suggested that aminoalkyl moiety, with the adequate chain length and substituent, could provide compound with the high potency and selectivity. This study suggests the 3,5-bis(aminopyrimidinyl)indole moiety is a very interesting scaffold, which can be further optimized for more potent inhibitors of pim kinases.

Bulletin of the Korean Chemical Society published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C4H3Cl2N3, Quality Control of 56-05-3.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Krasnov, Victor P. published the artcileSynthesis of Pyrimidine Conjugates with 4-(6-Amino-hexanoyl)-7,8-difluoro-3,4-dihydro-3-methyl-2H-[1,4]benzoxazine and Evaluation of Their Antiviral Activity, Application In Synthesis of 56-05-3, the publication is Molecules (2022), 27(13), 4236, database is CAplus and MEDLINE.

A series of pyrimidine conjugates containing a fragment of racemic 7,8-difluoro-3,4-dihydro-3-methyl-2H-[1,4]benzoxazine and its (S)-enantiomer attached via a 6-aminohexanoyl fragment were synthesized by the reaction of nucleophilic substitution of chlorine in various chloropyrimidines. Enantiomeric purity of optically active derivatives was confirmed by chiral HPLC. Antiviral evaluation of the synthesized compounds has shown that the replacement of purine with a pyrimidine fragment leads to a decrease in the anti-herpesvirus activity compared to the lead compound, purine conjugate. The studied compounds did not exhibit significant activity against influenza A (H1N1) virus.

Molecules published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C4H3Cl2N3, Application In Synthesis of 56-05-3.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Jagadeesha, Gullahalli S. published the artcileMicrowave-Assisted, Metal-Free, Chemoselective N -Formylation of Amines using 2-Formyl-3-methyl-1H-imidazol-3-ium Iodide and In Situ Synthesis of Benzimidazole and Isocyanides, SDS of cas: 56-05-3, the publication is SynOpen (2022), 6(2), 132-140, database is CAplus.

An efficient, environmentally benign, chemoselective, microwave-assisted N-formylation protocol of aromatic, aliphatic, alicyclic, benzylic amines, inactivated aromatic amines and sterically demanding heterocyclic amines using 2-formyl-1,3-dimethyl-1H-imidazol-3-ium iodide were developed. This afforded a series of N-substituted formamides RR¹NCHO [R = H, Me, Bn, R¹ = Me, t-Bu, Bn, etc., RR¹ = (CH₂)₄, (CH₂)₅; R = H, R¹ = Ph, 4-MeC₆H₄, 4-BrC₆H₄, etc.] with good to excellent yields (23 examples, 53-96% yield) and was readily scaled. The methodol. were further extended to synthesize benzimidazole and isocyanide derivatives

SynOpen published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C4H3Cl2N3, SDS of cas: 56-05-3.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Guo, Yinping published the artcileStructure-Guided Discovery of a Potent and Selective Cell-Active Inhibitor of SETDB1 Tudor Domain, COA of Formula: C7H6ClN3O, the publication is Angewandte Chemie, International Edition (2021), 60(16), 8760-8765, database is CAplus and MEDLINE.

SET domain bifurcated protein 1 (SETDB1) is a histone lysine methyltransferase that promotes the silencing of some tumor suppressor genes and is overexpressed in many cancers. SETDB1 contains a unique tandem tudor domain (TTD) that recognizes histone H3 sequences containing both methylated and acetylated lysines. Beginning with the identification of a hit compound (Cpd1, I), we discovered the first potent and selective small mol. SETDB1-TTD inhibitor (R,R)-59 (II) through stepwise structure-guided optimization. (R,R)-59 showed a K_D value of 0.088±0.045μM in the ITC assay. The high potency of (R,R)-59 was well explained by the cocrystal structure of the (R,R)-59-TTD complex. (R,R)-59 is an endogenous binder competitive inhibitor. Evidence has also demonstrated its cellular target engagement. Interestingly, the enantiomer (S,S)-59 did not show activity in all the assays, highlighting the potential of (R,R)-59 as a tool compound in exploring the biol. functions of SETDB1-TTD.

Angewandte Chemie, International Edition published new progress about 2351929-82-1. 2351929-82-1 belongs to pyrimidines, auxiliary class Pyrroles, name is 2-Chloro-3-methyl-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one, and the molecular formula is C7H6ClN3O, COA of Formula: C7H6ClN3O.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Bolli, Martin H. published the artcileNovel Benzo[1,4]diazepin-2-one Derivatives as Endothelin Receptor Antagonists, Computed Properties of 321565-33-7, the publication is Journal of Medicinal Chemistry (2004), 47(11), 2776-2795, database is CAplus and MEDLINE.

Since its discovery in 1988 by Yanagisawa et al., endothelin (ET), a potent vasoconstrictor, has been widely implicated in the pathophysiol. of cardiovascular, cerebrovascular, and renal diseases. Many research groups have embarked on the discovery and development of ET receptor antagonists for the treatment of such diseases. While several compounds, e.g., ambrisentan, are in late clin. trials for various indications, one compound (bosentan, Tracleer) is being marketed to treat pulmonary arterial hypertension. Inspired by the structure of ambrisentan, a novel class of ET receptor antagonists based on a 1,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-2-one scaffold was designed. The preparation as well as the in vitro and in vivo structure-activity relationships of these derivatives are reported. Potent dual ET_A/ET_B receptor antagonists with affinities in the low nanomolar range have been identified. In addition, several compounds efficiently reduced arterial blood pressure after oral administration to Dahl salt-sensitive rats. In this animal model, the efficacy of (αR,5R)-rel-α-[(4,6-dimethyl-2-pyrimidinyl)oxy]-2,3,4,5-tetrahydro-2-oxo-5-phenyl-1-[(2,4,6-trifluorophenyl)methyl]-1H-1,4-benzodiazepine-5-acetic acid (I) was superior to that of racemic ambrisentan.

Journal of Medicinal Chemistry published new progress about 321565-33-7. 321565-33-7 belongs to pyrimidines, auxiliary class Pyrimidine, name is 2-Chloro-5-methanesulfonylpyrimidine, and the molecular formula is C5H5ClN2O2S, Computed Properties of 321565-33-7.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Schaefer, Gabriel published the artcileFacile Synthesis of Sterically Hindered and Electron-Deficient Secondary Amides from Isocyanates, Quality Control of 56-05-3, the publication is Angewandte Chemie, International Edition (2012), 51(36), 9173-9175, S9173/1-S9173/52, database is CAplus and MEDLINE.

The authors report a convenient and rapid approach to the synthesis of hindered and electron-deficient amides by the direct coupling of isocyanates with Grignard reagents. The hindered isocyanates are readily prepared from either amines or carboxylic acids using well-established methods. The isocyanates are easily handled compounds that can be stored for months without any sign of decomposition, and many of them are com. available. The Grignard reagents used in this study are either com. obtained or are readily prepared from the corresponding organo halide and magnesium metal.

Angewandte Chemie, International Edition published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C4H3Cl2N3, Quality Control of 56-05-3.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Zhao, Y. published the artcileSynthesis and In Vitro Evaluation of Bis-intercalators with Varied Linkers between Aminochloropyrimidine Rings, Application of 2-Amino-4,6-dichloropyrimidine, the publication is Journal of Heterocyclic Chemistry (2014), 51(5), 1327-1332, database is CAplus.

The synthesis of two groups of aminochloropyrimidine bis-intercalators with different lipophilicity or limited flexibility of linkers as potential DNA intercalators is described. The lipophilic linkers in the synthesized bis-intercalators are represented by alternating methylene groups and oxygen atoms in a chain, with a pyrimidine ring containing an amino group and a chloro group at each end I [X = (CH₂)₂O(CH₂)₂O(CH₂)₂, (CH₂)₃O(CH₂)₂O(CH₂)₃, (CH₂)₃O(CH₂)₄O(CH₂)₃, (CH₂)₃O(CH₂)₂O(CH₂)₂O(CH₂)₃]. The bis-intercalators with limited flexibility contain chains with two benzene rings II [Y = CH₂C₆H₄CH₂, C₆H₄CH₂C₆H₄, C₆H₄(CH₂)₂C₆H₄, C₆H₄OC₆H₄, C₆H₄SC₆H₄]. All compounds I, II were obtained by nucleophilic substitution of 2-amino-4,6-dichloropyrimidine. The anticancer activity of these newly synthesized compounds I, II is also reported. The compounds III (n = 10, 12) described in one of our previous publications display good anticancer activity against murine lymphoma.

Journal of Heterocyclic Chemistry published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C3H5BN2O2, Application of 2-Amino-4,6-dichloropyrimidine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Zhou, Shengwang published the artcilePhotoactivatable Reaction for Covalent Nanoscale Patterning of Multiple Proteins, Category: pyrimidines, the publication is ACS Applied Materials & Interfaces (2018), 10(47), 40452-40459, database is CAplus and MEDLINE.

This article describes a photochem. approach for independently patterning multiple proteins to an inert substrate, particularly for studies of cell adhesion. A photoactivatable chloropyrimidine ligand was employed for covalent immobilization of SnapTag fusion proteins on self-assembled monolayers of alkanethiolates on gold. A two-step procedure was used: first, patterned UV illumination of the surface activated protein capture ligands, and second, incubation with a SnapTag fusion protein bound to the surface in illuminated regions. Two different fluorescent proteins were patterned in registry with features of 400 nm in size over a 1 mm² area. An example is given wherein an anti-carcinoembryonic antigen (anti-CEA) scFv antibody was patterned to direct the selective attachment of a human cancer cell line that express the CEA antigen. This method enables the preparation of surfaces with control over the d. and activity of independently patterned proteins.

ACS Applied Materials & Interfaces published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C25H29N9O3, Category: pyrimidines.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Li, Jian-Yuan published the artcilePalladium-Catalyzed Hydroxycarbonylation of (Hetero)aryl Halides for DNA-Encoded Chemical Library Synthesis, Category: pyrimidines, the publication is Bioconjugate Chemistry (2019), 30(8), 2209-2215, database is CAplus and MEDLINE.

A strategy for DNA-compatible, palladium-catalyzed hydroxycarbonylation of (hetero)aryl halides on DNA-chem. conjugates has been developed. This method generally provided the corresponding carboxylic acids in moderate to very good conversions for (hetero)aryl iodides and bromides, and in poor to moderate conversions for (hetero)aryl chlorides. These conditions were further validated by application within a DNA-encoded chem. library synthesis and subsequent discovery of enriched features from the library in selection experiments against two protein targets.

Bioconjugate Chemistry published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C4H3Cl2N3, Category: pyrimidines.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Sharif, Ehesan U. published the artcileDevelopment of a Scalable and Practical Synthesis of AB928, a Dual A_2a/A_2b Receptor Antagonist, Synthetic Route of 56-05-3, the publication is Organic Process Research & Development (2020), 24(7), 1254-1261, database is CAplus.

First- and second-generation routes to the dual A_2a/A_2b receptor antagonist AB928 I are disclosed. The second-generation route (performed on multigram scale) prepared the aminochloropyridinylbenzonitrile II by a route avoiding palladium-catalyzed borylation and Suzuki coupling reactions required in the initial route which generated significant amounts of byproducts.

Organic Process Research & Development published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C9H21NO3, Synthetic Route of 56-05-3.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia