Month: November 2022

Antibacterial Diamines Targeting Bacterial Membranes was written by Wang, Bo;Pachaiyappan, Boobalan;Gruber, Jordon D.;Schmidt, Michael G.;Zhang, Yong-Mei;Woster, Patrick M.. And the article was included in Journal of Medicinal Chemistry in 2016.Formula: C20H34N4O4 The following contents are mentioned in the article:

Antibiotic resistance is a growing threat to human health exacerbated by a lack of new antibiotics. We now describe a series of substituted diamines that produce rapid bactericidal activity against both Gram-pos. and Gram-neg. bacteria, including methicillin-resistant Staphylococcus aureus and stationary-phase bacteria. These compounds reduce biofilm formation and promote biofilm dispersal in Pseudomonas aeruginosa. The most potent analog, 3 (1,13-bis{[(2,2-diphenyl)-1-ethyl]thioureido}-4,10-diazatridecane), primarily acts by depolarization of the cytoplasmic membrane and permeabilization of the bacterial outer membrane. Transmission electron microscopy confirmed that 3 disrupts membrane integrity rapidly. Compound 3 is also synergistic with kanamycin, demonstrated by the checkerboard method and by time-kill kinetic experiments In human cell toxicity assays, 3 showed limited adverse effects against the HEK293T human kidney embryonic cells and A549 human adenocarcinoma cells. In addition, 3 produced no adverse effects on Caenorhabditis elegans development, survival, and reproduction Collectively, diamines related to 3 represent a new class of broad-spectrum antibacterials against drug-resistant pathogens. This study involved multiple reactions and reactants, such as Di-tert-butyl butane-1,4-diylbis((2-cyanoethyl)carbamatE) (cas: 194808-59-8Formula: C20H34N4O4).

Di-tert-butyl butane-1,4-diylbis((2-cyanoethyl)carbamatE) (cas: 194808-59-8) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Formula: C20H34N4O4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Large Electro-optic Activity and Enhanced Thermal Stability from Diarylaminophenyl-Containing High-β Nonlinear Optical Chromophores was written by Cheng, Yen-Ju;Luo, Jingdong;Hau, Steven;Bale, Denise H.;Kim, Tae-Dong;Shi, Zhengwei;Lao, David B.;Tucker, Neil M.;Tian, Yanqing;Dalton, Larry R.;Reid, Philip J.;Jen, Alex K.-Y.. And the article was included in Chemistry of Materials in 2007.Category: nitriles-buliding-blocks The following contents are mentioned in the article:

Two series of highly efficient and thermally stable nonlinear optical chromophores based on the (4-diarylamino)phenyl electron donors have been synthesized and systematically investigated. A modular approach has been employed to synthesize these electron donors with tunable size, shape, and electron-donating abilities. Efficient conjugated bridges were extended from these donors and coupled with very strong CF₃-TCF electron acceptors to afford chromophores with very high β values (up to 7077 × 10^-30 esu at 1.907 μm). These chromophores possess much higher thermal stability (with their onset decomposition temperatures all above 220 °C) than those substituted with (4-dialkylamino)phenyl donors. Most importantly, the high mol. hyperpolarizability of these chromophores can be effectively translated into very large electro-optic (E-O) coefficients (r₃₃) in poled polymers through suitable shape engineering. Exemplified by the chromophore B4, which has a fluorinated aromatic substituent anchored at its donor end, it showed a very large r₃₃ (169 pm/V) at 1.31 μm. This value is almost 1 order higher than the E-O activities usually reported for (4-diarylamino)phenyl-substituted NLO chromophores. This study involved multiple reactions and reactants, such as 4-((4-Methoxyphenyl)amino)benzonitrile (cas: 319016-04-1Category: nitriles-buliding-blocks).

4-((4-Methoxyphenyl)amino)benzonitrile (cas: 319016-04-1) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Cation selectivity of ionophores based on tripodal thiazole derivatives on benzene scaffold was written by Kim, Hong-Seok;Kim, Dong-Hyun;Kim, Ki Soo;Choi, Jun-Hyeak;Choi, Heung-Jin;Kim, Sung-Hoon;Shim, Jun Ho;Cha, Geun Sig;Nam, Hakhyun. And the article was included in Talanta in 2007.Synthetic Route of C15H15N3 The following contents are mentioned in the article:

The synthesis and potentiometric evaluation of new 1,3,5-tris(thiazolylcarbethoxy)-2,4,6-trimethylbenzene, 1,3,5-tris(thiazolylhydroxy)-2,4,6-trimethylbenzene, 1,3,5-tris(thiazolylmethyl)-2,4,6-trimethylbenzene, and 1,3,5-tris(thiazolylphenyl)-2,4,6-trimethylbenzene, toward mono and divalent cations under various pH conditions are outlined. The ion-selective properties of the newly synthesized compounds were studied by measuring the potentiometric responses of the 3-, 4-, 5-, and 6-based membrane electrodes to alkali metal, alk. earth metal, ammonium, and transition metal ions, under various pH conditions. The 3-based electrode exhibited a Nernstian response to ammonium and potassium under alk. pH conditions, while the other three electrodes showed a poor potentiometric performance. All electrodes showed substantial responses to silver ion under acidic condition, but there was almost nil response to other transition metal ions (Fe²⁺, Co²⁺, Zn²⁺, Ni²⁺, Pb²⁺, Cd²⁺, Cu²⁺ and Hg²⁺). The 3- and 5-based electrodes resulted in near Nernstian responses (51.3 mV and 59.5 mV/pAg⁺, resp.) with low detection limits (∼100 ppt), while the 4- and 6-based ones showed sub-Nernstian <40 mV/pAg⁺. The results were interpreted with semi-empirically modeled structures. This study involved multiple reactions and reactants, such as 2,2′,2”-(2,4,6-Trimethylbenzene-1,3,5-triyl)triacetonitrile (cas: 16144-65-3Synthetic Route of C15H15N3).

2,2′,2”-(2,4,6-Trimethylbenzene-1,3,5-triyl)triacetonitrile (cas: 16144-65-3) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Synthetic Route of C15H15N3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Syntheses of a library of molecules on the marine natural product ianthelliformisamines platform and their biological evaluation was written by Khan, Faiz Ahmed;Ahmad, Saeed;Kodipelli, Naveena;Shivange, Gururaj;Anindya, Roy. And the article was included in Organic & Biomolecular Chemistry in 2014.Electric Literature of C20H34N4O4 The following contents are mentioned in the article:

Ianthelliformisamines A (I), B (II), and C (III) are a novel class of bromotyrosine-derived antibacterial agents isolated recently from the marine sponge Suberea ianthelliformis. We have synthesized ianthelliformisamines A-C straightforwardly by the condensation of (E)-3-(3,5-dibromo-4-methoxyphenyl)acrylic acid and the corresponding Boc-protected polyamine followed by Boc-deprotection with TFA. Further, using this reaction protocol, a library of their analogs (39 analogs) has been synthesized by employing 3-phenylacrylic acid derivatives and Boc-protected polyamine chains through various combinations of these two fragments differing in Ph ring substitution, double bond geometry or chain length of the central spacer of the polyamine chain. All the synthesized compounds (ianthelliformisamines A-C and their analogs) were screened for antibacterial activity against both Gram-neg. (Escherichia coli) and Gram-pos. (Staphylococcus aureus) strains. All synthetic analogs of ianthelliformisamine A showed bacterial growth inhibition against both strains (Escherichia coli and Staphylococcus aureus), having MIC values in the range of 117.8-0.10 μM, while none of the synthetic analogs of ianthelliformisamine C as well as the parent compound showed any detectable antibacterial activity. Interestingly, some of the synthetic analogs of ianthelliformisamines A and B exerted a bactericidal effect against both E. coli and S. aureus strains, decreasing viable bacterial count by 99% at concentrations as low as 2 × MIC. This study involved multiple reactions and reactants, such as Di-tert-butyl butane-1,4-diylbis((2-cyanoethyl)carbamatE) (cas: 194808-59-8Electric Literature of C20H34N4O4).

Di-tert-butyl butane-1,4-diylbis((2-cyanoethyl)carbamatE) (cas: 194808-59-8) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Electric Literature of C20H34N4O4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Tripodal (N-alkylated) CMP(O) and malonamide ligands: synthesis, extraction of metal ions, and potentiometric studies was written by Janczewski, Dominik;Reinhoudt, David N.;Verboom, Willem;Malinowska, Elzbieta;Pietrzak, Mariusz;Hill, Clement;Allignol, Cecile. And the article was included in New Journal of Chemistry in 2007.Synthetic Route of C15H15N3 The following contents are mentioned in the article:

Tripodal ligands build on the C-pivot (9b-e, 13b-d, and 17a-d) and trialkylbenzene platforms (10a,b, 11, 12, 14a,b, and 18a,b) bearing (N-alkylated) carbamoylmethylphosphine oxide (CMPO), carbamoylmethylphosphonate (CMP), and malonamide moieties were synthesized. Extraction studies with Am³⁺ and Eu³⁺ show that in general there is a pos. influence of the N-alkyl substituents in C-pivot CMP(O) ligands on the D (distribution) coefficients The trialkylbenzene CMPO ligands 10a,b, 11, and 12 have considerably larger D coefficients than the corresponding C-pivot analogs 9a-e, although hardly having any selectivity, while N-alkylation gives rise to smaller D coefficients Although less effective the extraction behavior of the C-pivot CMP analogs 13b-d shows more or less the same trend as the corresponding CMPO ligands 9b-e upon substitution of the carboxamide N-atom with different alkyl chains. The different malonamide ligands 17a-d and 18a,b are bad extractants, while N-alkylation makes them even worse. Potentiometric studies of CMP(O) and malonamide ligands in polymeric membranes on Pb²⁺, Cu²⁺, Ca²⁺, Mg²⁺, Na⁺, and K⁺ salts revealed that N-alkyl substituents increase the stability constants of ion-ionophore complexes compared to unsubstituted ligands. In polymeric membrane electrodes the ligands induce a selectivity pattern that differs significantly from the so-called Hofmeister series, giving the highest selectivity coefficients for UO₂²⁺ among all examined cations (Pb²⁺, Cu²⁺, Ca²⁺, Mg²⁺, Na⁺, K⁺). This study involved multiple reactions and reactants, such as 2,2′,2”-(2,4,6-Trimethylbenzene-1,3,5-triyl)triacetonitrile (cas: 16144-65-3Synthetic Route of C15H15N3).

2,2′,2”-(2,4,6-Trimethylbenzene-1,3,5-triyl)triacetonitrile (cas: 16144-65-3) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Synthetic Route of C15H15N3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and anion-selective complexation of homobenzylic tripodal thiourea derivatives was written by Hisaki, Ichiro;Sasaki, Shin-Ichi;Hirose, Keiji;Tobe, Yoshito. And the article was included in European Journal of Organic Chemistry in 2007.Synthetic Route of C15H15N3 The following contents are mentioned in the article:

Cryptand- and tripod-type thiourea derivatives I [R = n-Bu (II), Bn (III), Ph (IV), p-nitrophenyl (V)] which have binding functionalities at the homobenzylic positions, were synthesized as possible neutral receptors toward anions with an expectation that the three binding sites work cooperatively to bind an anion selectively. ¹H NMR spectroscopic monitoring of the titration of cryptand-type thiourea derivative with CH₃CO₂^–, Cl^–, and F^– in CDCl₂CDCl₂ at 100 °C showed that the binding constants were considerably smaller than those of I, presumably owing to the presence of strong intramol. hydrogen bonding in cryptand-type thiourea derivatives Complexation constants of I with H₂PO₄^–, CH₃CO₂^–, Cl^–, and Br^– anions were evaluated by ¹H NMR and/or UV/Vis spectroscopic anal. of the titration in DMSO. Though II and III undergo complexation with phosphate anion in a 1:1 stoichiometry, their association constants were not as large as simple reference compound, N,N’-dibenzyl thiourea, probably because of the steric hindrance around the binding sites and the large entropy cost for cooperative binding. IV exhibits complexation in a 1:2 stoichiometry with H₂PO₄– and CH₃CO₂^–, whereas it forms 1:1 complexes with chloride and bromide anions because of the subtle balance between the steric hindrance and the binding ability. However, by increasing the acidity of the thiourea functionality, V exhibited remarkably enhanced binding ability and selectivity toward H₂PO₄^– compared to those of reference compound, N-(4-nitrophenyl)-N’-(2-phenylethyl) thiourea, presumably through cooperative complexation of the three binding sites to the guest anion. This study involved multiple reactions and reactants, such as 2,2′,2”-(2,4,6-Trimethylbenzene-1,3,5-triyl)triacetonitrile (cas: 16144-65-3Synthetic Route of C15H15N3).

2,2′,2”-(2,4,6-Trimethylbenzene-1,3,5-triyl)triacetonitrile (cas: 16144-65-3) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Synthetic Route of C15H15N3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some derivatives of 4′-hydroxydiphenylamine-4-carboxylic acid was written by Burger, Alfred;Darby, Robert A.. And the article was included in Journal of the American Chemical Society in 1955.Category: nitriles-buliding-blocks The following contents are mentioned in the article:

p-HOC₆H₄NHPh (260 g.), 375 g. Bz₂O, and 250 cc. dry pyridine heated 6 h. on the steam bath, the cooled mixture acidified with cold 50% H₂SO₄ and filtered, the brownish residue washed with 2% aqueous NaOH and H₂O, treated with EtOH and diluted with H₂O, and the precipitate crystallized from aqueous EtOH gave 330 g. p-BzOC₆H₄NHPh, pale yellow leaflets, m. 112-14°. p-BzOC₆H₄NHC₆H₄Br-p (40 g.) and 16 g. CuCN in 240 cc. dry quinoline refluxed 6 h., the red solution cooled and poured with stirring into 200 cc. 37% HCl, and the precipitate filtered, washed, and recrystallized from C₆H₆-ligroine gave 17.5 g. p-BzOC₆H₄NHC₆H₄CN-p (I), almost colorless needles, m. 178.5-80.5° (all m.ps. are corrected). I treated 0.5 h. with hot KOH in EtOH gave 71% p-HOC₆H₄NHC₆H₄CN-p (II), m. 193-4.5° (from aqueous EtOH). II treated with CH₂N₂ gave the Me ether (III), m. 99-100° (from aqueous Me₂CO). III refluxed 20 h. with 15% alc. KOH yielded 43% p-MeOC₆H₄NHC₆H₄CO₂H-p (IV), m. 165-7° (from MeOH). II (5 g.) in 40 cc. (CH₂OH)₂ containing 6 g. KOH refluxed 3 h., cooled, acidified, and filtered, and the brown crystalline filter residue recrystallized with Darco from MeOH yielded 3.56 g. p-HOC₆H₄NHC₆H₄CO₂H-p, colorless crystals, m. 229-30° (decomposition) (it turned pink in air), which treated with CH₂N₂ gave the Me ester of IV, m. 91.5-3.5° (from Et₂O-ligroine). II (0.1 mol) treated with 0.4 mol ICl and the resulting pink powder (which turned blue in air) recrystallized repeatedly from Et₂O-ligroine gave 30% 3,5,4-Cl₂(HO)C₆H₂NHC₆H₄CN-p, almost transparent colorless needles, m. 215-16° (from Et₂O-ligroine). This study involved multiple reactions and reactants, such as 4-((4-Methoxyphenyl)amino)benzonitrile (cas: 319016-04-1Category: nitriles-buliding-blocks).

4-((4-Methoxyphenyl)amino)benzonitrile (cas: 319016-04-1) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Polar self-assembly: steric effects leading to polar mixed-ligand coordination cages was written by Zhang, Jianyong;Miller, Philip W.;Nieuwenhuyzen, Mark;James, Stuart L.. And the article was included in Chemistry – A European Journal in 2006.Application In Synthesis of 2,2′,2”-(2,4,6-Trimethylbenzene-1,3,5-triyl)triacetonitrile The following contents are mentioned in the article:

The authors present a highly unusual example of self-assembly, specifically a polar, mixed-ligand cage which forms in preference to sym. homoligand products, and which suggests that steric effects can be exploited to obtain novel nonuniform polyhedral cages. In particular, reaction between the bulky tripodal triphosphine 2,4,6-tris(diphenylphosphino)triazine, L1, the nonbulky tripodal trinitrile 2,4,6-tris(cyanomethyl)trimethylbenzene, L2 and AgSbF₆ in a 3:1:4 ratio gives the mixed-ligand aggregate [Ag₄(L1)₃(L2)(SbF₆)]³⁺, 1-SbF₆, instantly as the only product in quant. yield. The x-ray crystal structure of complex 1-SbF₆ is consistent with the suspected solution-state structure. The cage derives from trigonal-pyramidal geometry, the basal vertexes of which are defined by three bulky triphosphines, L1, and the apical vertex by the nonbulky trinitrile, L2. There is apical elongation amounting to 19% in comparison to the ideal uniform tetrahedron. The cage also encapsulates an SbF₆ anion. ¹⁹F NMR spectra in solution for the analogous PF₆ complex [Ag₄(L1)₃(L2)(PF₆)]³⁺, 1-PF₆, confirm that one anion is also encapsulated in solution The synthesis of the analogous CF₃SO₃^– complex, [Ag₄(L1)₃(L2)(OTf)]³⁺, 1-OTf, in solution is also described, although 1-PF₆ and 1-OTf could not be isolated due to slow decomposition in solution The selective formation of these mixed-ligand cages is discussed in terms of ligand-ligand and ligand-included anion steric repulsions, which the authors propose prevent the formation of the competing hypothetical homoligand tetrahedral structure [Ag₄(L1)₄(SbF₆)]³⁺, and thus favor the mixed ligand cage. Cage cone angles for L1 and L2 are estimated at 115° and 101°, resp. Variable-temperature ³¹P NMR spectroscopy shows that complex 1-SbF₆ and the related previously reported partial tetrahedral complex [Ag₄(L1)₃(anion)]³⁺ undergo dynamic twisting processes in solution between enantiomeric C₃-symmetry conformations. This study involved multiple reactions and reactants, such as 2,2′,2”-(2,4,6-Trimethylbenzene-1,3,5-triyl)triacetonitrile (cas: 16144-65-3Application In Synthesis of 2,2′,2”-(2,4,6-Trimethylbenzene-1,3,5-triyl)triacetonitrile).

2,2′,2”-(2,4,6-Trimethylbenzene-1,3,5-triyl)triacetonitrile (cas: 16144-65-3) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Application In Synthesis of 2,2′,2”-(2,4,6-Trimethylbenzene-1,3,5-triyl)triacetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts