Category: 194808-59-8

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

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Nitrile – Wikipedia,
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Solid-Phase synthesis of diamine and polyamine amino acid derivatives as HIV-1 tat-TAR binding inhibitors was written by Jimenez Bueno, G.;Klimkait, T.;Gilbert, I. H.;Simons, C.. And the article was included in Bioorganic & Medicinal Chemistry in 2003.Formula: C20H34N4O4 The following contents are mentioned in the article:

A series of diamine and polyamine derivatives, either free amines or salts (HCl or TFA), of aspartic and glutamic acid were prepared in excellent yields using Rink Amide solid-phase synthesis. The asparagine and glutamine derivatives were all evaluated for their ability to inhibit Tat-TAR binding using a FIGS (fusion induced gene stimulating) cellular assay, with the polyamine derivatives exhibiting the most promising binding activity. 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. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Formula: C20H34N4O4

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Mild and Efficient Synthesis of N¹,N⁵,N¹⁰-Tri-tert-butoxycarbonyl Spermine was written by Feng, Xiangjun;Xia, Wenpin;Luo, Yu;Lu, Wei. And the article was included in Synthetic Communications in 2012.Product Details of 194808-59-8 The following contents are mentioned in the article:

This article describes a mild and efficient synthesis of N¹,N⁵,N¹⁰-tri-tert-butoxycarbonyl spermine from putrescine, with a 41% overall yield. The key steps include a Michael addition and Raney nickel (W-2) reduction The advantages of this synthesis include a simple procedure, mild conditions, and good yields. This study involved multiple reactions and reactants, such as Di-tert-butyl butane-1,4-diylbis((2-cyanoethyl)carbamatE) (cas: 194808-59-8Product Details of 194808-59-8).

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. 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. Product Details of 194808-59-8

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Sinulamide: an H,K-ATPase inhibitor from a soft coral Sinularia sp. was written by Sata, Noriko U.;Sugano, Michihiro;Matsunaga, Shigeki;Fusetani, Nobuhiro. And the article was included in Tetrahedron Letters in 1999.Reference of 194808-59-8 The following contents are mentioned in the article:

Sinulamide (I·3Cl^–), a new tetraprenylated spermine derivative, has been isolated from a soft coral Sinularia sp. as an H,K-ATPase inhibitor. The structure was assigned on the basis of spectroscopic data and confirmed by a total synthesis. This study involved multiple reactions and reactants, such as Di-tert-butyl butane-1,4-diylbis((2-cyanoethyl)carbamatE) (cas: 194808-59-8Reference of 194808-59-8).

Di-tert-butyl butane-1,4-diylbis((2-cyanoethyl)carbamatE) (cas: 194808-59-8) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Reference of 194808-59-8

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Analogues of polyamine alkaloids and their synthetic advantages was written by Li, Yi;Popaj, Kasim;Lochner, Martin;Geneste, Herve;Budriesi, Roberta;Chiarini, Alberto;Melchiorre, Carlo;Hesse, Manfred. And the article was included in Farmaco in 2001.Synthetic Route of C20H34N4O4 The following contents are mentioned in the article:

Several polyamine derivatives were synthesized in order to produce novel antagonists of muscular nicotinic acetylcholine receptors. Their affinities were compared with those of philanthotoxin PhTX-343. This study involved multiple reactions and reactants, such as Di-tert-butyl butane-1,4-diylbis((2-cyanoethyl)carbamatE) (cas: 194808-59-8Synthetic Route of C20H34N4O4).

Di-tert-butyl butane-1,4-diylbis((2-cyanoethyl)carbamatE) (cas: 194808-59-8) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Synthetic Route of C20H34N4O4

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Nitrile – Wikipedia,
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Synthesis and Biological Evaluation of s-Triazine Substituted Polyamines as Potential New Anti-Trypanosomal Drugs was written by Klenke, Burkhard;Stewart, Mhairi;Barrett, Michael P.;Brun, Reto;Gilbert, Ian H.. And the article was included in Journal of Medicinal Chemistry in 2001.Name: Di-tert-butyl butane-1,4-diylbis((2-cyanoethyl)carbamatE) The following contents are mentioned in the article:

The P2 transporter is a nucleoside transporter which is unique to the protozoan parasite Trypanosoma brucei, the causative organism of Human African Trypanosomiasis. The transporter has been shown to bind some structural motifs not recognized by other transporters. In this paper we describe the use of the melamine motif, a substrate of the P2 transporter, as a potential tool to selectively deliver polyamine analogs to the parasites. The synthesis of a number of polyamine analogs attached to a variety of melamine analogs is described. Many of the compounds were shown to competitively inhibit uptake of adenosine, indicating that they are recognized by the transporter. Some of the compounds showed good in vitro activity against the parasites. This study involved multiple reactions and reactants, such as Di-tert-butyl butane-1,4-diylbis((2-cyanoethyl)carbamatE) (cas: 194808-59-8Name: Di-tert-butyl butane-1,4-diylbis((2-cyanoethyl)carbamatE)).

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. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Name: Di-tert-butyl butane-1,4-diylbis((2-cyanoethyl)carbamatE)

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Nitrile – Wikipedia,
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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

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

Template Oligomerization of DNA-Bound Cations Produces Calibrated Nanometric Particles was written by Blessing, Thomas;Remy, Jean-Serge;Behr, Jean-Paul. And the article was included in Journal of the American Chemical Society in 1998.SDS of cas: 194808-59-8 The following contents are mentioned in the article:

A general approach to the monomol. condensation of DNA into stable nano-metric particles is reported, which may be extended to the design of any kind of calibrated nano-metric particles required for material sciences. The process takes advantage of the low cooperativity of binding small monomeric counterions to a macromol. polyion, followed by a zipper-oligomerization reaction which “freezes” the resulting condensed particles. The DNA particles have a neg. surface charge which ensures colloid stability and in vivo diffusion, yet makes them unsuitable for carrying DNA into cells. Thus, C-sper-C [cysteine-spermine-cysteine (I)] was synthesized and mixed with plasmid DNA, which was found to enhance the thiol oxidation rates in the thiol/disulfide oligomerization, which resulted in condensation of the DNA into particles of mean size 50 ± 15 nm, which were stable ≥1 wk. The condensed particles were stable in electrophoresis conditions, but addition of excess dithiothreitol of raising the ionic concentration to physiol. levels converted the cationic polymer back to I. This study involved multiple reactions and reactants, such as Di-tert-butyl butane-1,4-diylbis((2-cyanoethyl)carbamatE) (cas: 194808-59-8SDS of cas: 194808-59-8).

Di-tert-butyl butane-1,4-diylbis((2-cyanoethyl)carbamatE) (cas: 194808-59-8) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).SDS of cas: 194808-59-8

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

(Bis)urea and (Bis)thiourea Inhibitors of Lysine-Specific Demethylase 1 as Epigenetic Modulators was written by Sharma, Shiv K.;Wu, Yu;Steinbergs, Nora;Crowley, Michael L.;Hanson, Allison S.;Casero, Robert A. Jr.;Woster, Patrick M.. And the article was included in Journal of Medicinal Chemistry in 2010.Computed Properties of C20H34N4O4 The following contents are mentioned in the article:

The recently discovered enzyme lysine-specific demethylase 1 (LSD1) plays an important role in the epigenetic control of gene expression, and aberrant gene silencing secondary to LSD1 overexpression is thought to contribute to the development of cancer. We recently reported a series of (bis)guanidines and (bis)biguanides that are potent inhibitors of LSD1 and induce the re-expression of aberrantly silenced tumor suppressor genes in tumor cells in vitro. We now report a series of isosteric ureas and thioureas that are also potent inhibitors of LSD1. These compounds induce increases in methylation at the histone 3 lysine 4 (H3K4) chromatin mark, a specific target of LSD1, in Calu-6 lung carcinoma cells. In addition, these analogs increase cellular levels of secreted frizzle-related proteins (SFRP) 2 and 5 and transcription factor GATA4. These compounds represent an important new series of epigenetic modulators with the potential for use as antitumor agents. This study involved multiple reactions and reactants, such as Di-tert-butyl butane-1,4-diylbis((2-cyanoethyl)carbamatE) (cas: 194808-59-8Computed Properties of C20H34N4O4).

Di-tert-butyl butane-1,4-diylbis((2-cyanoethyl)carbamatE) (cas: 194808-59-8) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Computed Properties of C20H34N4O4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts