Tag: M.W=150-200

Nilsson, Jonas W.; Kvarnstroem, Ingemar; Musil, Djordje; Nilsson, Ingemar; Samulesson, Bertil published the artcile< Synthesis and SAR of Thrombin Inhibitors Incorporating a Novel 4-Amino-Morpholinone Scaffold: Analysis of X-ray Crystal Structure of Enzyme Inhibitor Complex>, Quality Control of 617-55-0, the main research area is amino morpholinone scaffold preparation thrombin inhibition crystal; structure activity relationship amino morpholinone scaffold thrombin inhibitor.

A 4-amino-2-carboxymethyl-3-morpholinone structural motif derived from malic acid has been used to mimic D-Phe-Pro in the thrombin inhibiting tripeptide D-Phe-Pro-Arg. The arginine in D-Phe-Pro-Arg was replaced by the more rigid P1 truncated p-amidinobenzylamine (Pab). These new thrombin inhibitors were used to probe the inhibitor binding site of α-thrombin. The best candidate in this series of thrombin inhibitors exhibits an in vitro IC50 of 0.130 μM. Interestingly, the stereochem. of the 4-amino-2-carboxymethyl-3-morpholinone motif is reversed for the most active compounds compared to that of a previously reported 2-carboxymethyl-3-morpholinone series. The X-ray crystal structure of the lead inhibitor cocrystd. with α-thrombin is discussed.

Journal of Medicinal Chemistry published new progress about Crystal structure. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Quality Control of 617-55-0.

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

Liu, Bin; Hu, Longqin published the artcile< 5'-(2-Nitrophenylalkanoyl)-2'-deoxy-5-fluorouridines as potential prodrugs of FUDR for reductive activation>, COA of Formula: C9H9NO4, the main research area is FUDR nitro containing prodrug preparation reduction cyclization; aminophenylalkanoate ester FUDR prodrug preparation reduction cyclization.

Four 5′-(2-nitrophenylalkanoyl)-2′-deoxy-5-fluorouridines (1a-d) were designed and synthesized as potential prodrugs of FUDR for reductive activation. Two Me groups were introduced α to the ester carbonyl to increase both the rate of cyclization activation and the stability of the conjugates towards serum esterases. Chem. reduction of the nitro group into an amino leads to cyclization and release of the active FUDR. Kinetic anal. of the cyclization activation process indicates that the two Me groups α to the ester carbonyl restrict the rotational freedom of ground state mol. and promote the cyclization reaction. However, the two Me groups also were found to render the conjugates as poor substrates of E. coli B nitroreductase. Conjugate 1c, without the two Me groups, was reduced by E. coli B nitroreductase (t1/2 = 8 h) to give two products, a N-hydroxyl lactam and the drug FUDR, suggesting that the enzymic reduction and subsequent cyclization activation proceeded through the hydroxylamine intermediate. These results indicate that cyclization activation will occur once the nitro group is reduced either to an amino or to a hydroxylamino group. The fact that the amino intermediates cyclized easily to release the incorporated drug FUDR suggests the feasibility of using peptide-linked acyl 2-aminophenylalkanoic acid esters as potential prodrugs for proteolytic activation.

Bioorganic & Medicinal Chemistry published new progress about Blood serum (prodrugs stability in human blood serum). 30095-98-8 belongs to class esters-buliding-blocks, and the molecular formula is C9H9NO4, COA of Formula: C9H9NO4.

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

Secrist, John A. III; Hickey, Charles J.; Norris, Robert E. published the artcile< A convenient total synthesis of (±)-(7E,9E)-trisporic acid B methyl ester>, SDS of cas: 60705-25-1, the main research area is total synthesis methyl trisporate; trisporic acid B total synthesis.

The title compound I was totally synthesized using as a key step a Michael-aldol sequence on MeO2CCHMeCOCH(OMe)2 to give cyclohexenone II.

Journal of Organic Chemistry published new progress about 60705-25-1. 60705-25-1 belongs to class esters-buliding-blocks, and the molecular formula is C7H12O5, SDS of cas: 60705-25-1.

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

Orita, Akihiro; Tanahashi, Chiaki; Kakuda, Atsushi; Otera, Junzo published the artcile< Highly Powerful and Practical Acylation of Alcohols with Acid Anhydride Catalyzed by Bi(OTf)3>, Recommanded Product: (S)-Dimethyl 2-hydroxysuccinate, the main research area is alc acylation anhydride bismuth triflate catalyst.

Bi(OTf)3-catalyzed acylation of alcs. with acid anhydride was evaluated in comparison with other acylation methods. The Bi(OTf)3-acid anhydride protocol was so powerful that sterically demanding or tertiary alcs. could be acylated smoothly. Less reactive acylation reagents such as benzoic and pivalic anhydride are also activated by this catalysis. In these cases, a new technol. was developed in order to overcome difficulty in separation of the acylated product from the remaining acylating reagent: methanolysis of the unreacted anhydride into easily separable Me ester realized quite easy separation of the desired acylation product. The Bi(OTf)3-acid anhydride protocol was applicable to a wide spectrum of alcs. bearing various functionalities. Acid-labile THP- or TBS-protected alc., furfuryl alc., and geraniol could be acylated as well as base-labile alcs. Even acylation of functionalized tertiary alcs. was effected at room temperature

Journal of Organic Chemistry published new progress about Acylation. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Recommanded Product: (S)-Dimethyl 2-hydroxysuccinate.

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

Lounasmaa, Mauri; Johansson, Carl J. published the artcile< Synthetic studies in the alkaloid field. IV. The sodium dithionite reduction of 1-[2-(3-indolyl)-ethyl]-3-methoxycarbonylpyridinium bromides>, Quality Control of 33402-75-4, the main research area is indoloquinolizine; reduction indolyl pyridinium dithionite; ring closure indolyl pyridine; alkaloid vallesiachotamine model.

Na dithionite reduction of the 1-[2-(3-indolyl)ethyl]-3-(methoxycarbonyl)pyridinium bromides I (R = H, Me, Pr) in NaHCO3-buffered medium gave 49-67% of the 1,4-dihydro derivatives II, whereas in unbuffered medium 58-62% of the indoloquinolizines III were formed. Acid-induced cyclization of II (R = H) gave 94% III (R = H) whereas II (R = Me, Pr) gave 91 and 86% resp. IV (R = Me, Pr). The stereochem. of the products were deduced from 13C NMR spectra. The use of Na dithionite reduction in the preparation of vallesiachotamine models is discussed.

Tetrahedron published new progress about Cyclization. 33402-75-4 belongs to class esters-buliding-blocks, and the molecular formula is C8H9NO2, Quality Control of 33402-75-4.

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

Pattenden, Gerald; Critcher, Douglas J.; Remuinan, Modesto published the artcile< Total synthesis of (-)-pateamine A, a novel immunosuppressive agent from Mycale sp>, Safety of (S)-Dimethyl 2-hydroxysuccinate, the main research area is asym synthesis pateamine A Stille coupling reaction; sulfinimine chiral auxiliary beta amino ester preparation pateamine A.

A convergent synthesis of the unique thiazole-containing polyene bis-lactone pateamine A (I) isolated from the marine sponge Mycale sp is described. The synthesis features the ubiquitous Stille sp2-sp2 coupling reaction to elaborate the E,Z-diene macrolide core and the all-E polyenamine side chain in the natural product. It also highlights the scope for enantiopure sulfinimine intermediates in the synthesis of chiral β-amino ester moieties in complex structures.

Canadian Journal of Chemistry published new progress about Chiral auxiliary. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Safety of (S)-Dimethyl 2-hydroxysuccinate.

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

Embrey, Samuel J.; Barrios-Perez, Carlos; Bunce, Richard A. published the artcile< (±)- cis-4a-alkyl -1,3,4,4a,9, 9a-hexahydro-2H -carbazol-2-ones by domino nitro reduction-aza-Michael addition to enones>, Category: esters-buliding-blocks, the main research area is cis alkyl hexahydro carbazolone preparation; enone domino nitro reduction aza Michael addition.

A domino nitro reduction-aza-Michael addition sequence was investigated for α,β-unsaturated ketones and compared with the analogous reaction for conjugated esters. As expected, six-membered ring closures of ketones did not proceed as well as for esters (<60% vs. >85%) due to the greater inherent reactivity of the ketones. This problem was minimized by performing the cyclization at lower temperature for a shorter time. The process had been extended to a synthesis of (±)-cis-4a-alkyl-1,3,4,4a,9,9a-hexahydro-2H-carbazol-2-ones I [R = Me, Et, n-Pr, Bn] with good yields (65%-86%). While the rigidity of the system and closure of the smaller five-membered ring created some strain in the products, yields were acceptable. The cis ring junction resulted from axial attack to gave a more stable chair-like enol that tautomerized to the target heterocycle.

Journal of Heterocyclic Chemistry published new progress about Aza-Michael reaction. 30095-98-8 belongs to class esters-buliding-blocks, and the molecular formula is C9H9NO4, Category: esters-buliding-blocks.

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

Malcor, Jean-Daniel; Brouillette, Yann; Graffion, Julien; Spielmann, Kim; Masurier, Nicolas; Maillard, Ludovic T.; Martinez, Jean; Lisowski, Vincent published the artcile< Synthesis and reactivity of pyrrolo[3,2-d][1,3]oxazine-2,4-dione. Access to new pyrrolo[3,2-e][1,4]diazepine-2,5-diones>, Safety of Ethyl 3-amino-1H-pyrrole-2-carboxylate, the main research area is pyrrolodiazepinedione preparation nucleophile reactivity.

A convenient synthesis of pyrrolo[3,2-d][1,3]oxazine-2,4-dione is described and its reactivity towards various nucleophiles studied. The regioselective ring opening of pyrrolo[3,2-d][1,3]oxazine-2,4-dione or its N-alkylated analog in the presence of alanine or proline afforded, resp., imidazolidinedione and 2 N-protected pyrrolo[3,2-e][1,4]diazepines in a one-pot process. In a last part of this study, an alternative route to produce a library of eight non protected pyrrolo[3,2-e][1,4]diazepine-2,5-diones is described to overcome the limited reactivity of pyrrolo[3,2-d][1,3]oxazine-2,4-dione.

Tetrahedron published new progress about Nucleophiles. 252932-48-2 belongs to class esters-buliding-blocks, and the molecular formula is C7H10N2O2, Safety of Ethyl 3-amino-1H-pyrrole-2-carboxylate.

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

Lo, Ho Yin; Bentzien, Jorg; White, Andre; Man, Chuk C.; Fleck, Roman W.; Pullen, Steven S.; Khine, Hnin Hnin; King, Josephine; Woska, Joseph R. Jr.; Wolak, John P.; Kashem, Mohammed A.; Roth, Gregory P.; Takahashi, Hidenori published the artcile< 2-Aminobenzimidazoles as potent ITK antagonists: de novo design of a pyrrole system targeting additional hydrogen bonding interaction>, SDS of cas: 7126-50-3, the main research area is aminobenzimidazole derivative preparation ITK antagonist.

Based on information from mol. modeling, a series of 2-aminobenzimidazoles with pyrrole moieties were designed and synthesized as ITK antagonists. Results showed that a significant improvement of intrinsic and cell-based potency was achieved. X-ray crystallog. anal. of an inhibitor complex with ITK confirmed the prediction from the de novo design that the pyrrole moiety of the inhibitor would form an addnl. hydrogen bonding interaction with Glu436 in the catalytic domain, and hence improve overall binding affinity of the inhibitor.

Tetrahedron Letters published new progress about Anti-inflammatory agents. 7126-50-3 belongs to class esters-buliding-blocks, and the molecular formula is C8H9NO3, SDS of cas: 7126-50-3.

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

Yang, Zan; Cao, Ting; Liu, Si; Li, An; Liu, Kun; Yang, Tao; Zhou, Congshan published the artcile< Transition-metal-free S-N bond formation: synthesis of 5-amino-1,2,4-thiadiazoles from isothiocyanates and amidines>, Application In Synthesis of 19241-24-8, the main research area is thiadiazole amino preparation regioselective green chem; amidine isothiocyanate tandem radical oxidative cyclization.

A novel and green method for the synthesis of 5-amino-1,2,4-thiadiazoles I (R1 = Me, cyclopropyl, 4-fluorophenyl, pyridin-3-yl, 1H-pyrazol-1-yl, etc.; R2 = tert-Bu, benzyl, naphth-1-yl, etc.) has been developed by the reaction of isothiocyanates R2N=C=S with amidines R1C(=NH)NH2.HCl. This protocol which is free of metal, catalyst and iodine involves O2 oxidative S-N bond formation for the synthesis of various 5-amino-1,2,4-thiadiazole derivatives I with excellent to good yields. High regioselectivity, mild reaction conditions, broad substrate scope and good functional group tolerance are the highlights of the report.

New Journal of Chemistry published new progress about Amidines Role: RCT (Reactant), RACT (Reactant or Reagent). 19241-24-8 belongs to class esters-buliding-blocks, and the molecular formula is C11H13NS, Application In Synthesis of 19241-24-8.

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