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'Foxtrot' fumarate: a water-soluble salt of N,N-di-allyl-5-methoxytryptamine (5-MeO-DALT).

ABSTRACT: The title compound, bis-(N,N-diallyl-5-meth-oxy-tryptammonium) (5-MeO-DALT) fumarate (systematic name: bis-{N-[2-(5-meth-oxy-1H-indol-3-yl)eth-yl]- N-(prop-2-en-1-yl)prop-2-en-1-aminium} (E)-but-2-enedioate), 2C₁₇H₂₃N₂O⁺·C₄H₂O₄ ^2-, has a single tryptammonium cation and half of a fumarate dianion in the asymmetric unit. The tryptammonium and fumarate ions are held together in one-dimensional chains by a series of N-H⋯O hydrogen bonds. These chains are combinations of R ⁴ ₄(22) rings, and C ² ₂(14) and C ⁴ ₄(28) parallel chains along [111].

SUBMITTER: Pham DNK

PROVIDER: S-EPMC8025863 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Water-Soluble Pd Nanoparticles for the Anti-Markovnikov Oxidation of Allyl Benzene in Water.

Project description:The catalytic activity and selectivity of two different water-soluble palladium nanoparticles capped with 5-(trimethylammonio)pentanethiolate and 6-(carboxylate)hexanethiolate ligands are investigated using the catalytic reaction of allyl benzene. The results show that the regioselective transformation of allyl benzene to 3-phenylpropanal occurs at room temperature and under atmospheric pressure in neat water via a Tsuji-Wacker type oxidation. Conventionally, the Tsuji-Wacker oxidation promotes the Markovnikov oxidation of terminal alkenes to their respective ketones in the presence of dioxygen. Water-soluble Pd nanoparticles, however, catalyze the anti-Markovnikov oxidation of allyl benzene to 3-phenylpropanal in up to 83% yields. Catalytic results of other aromatic alkenes suggest that the presence of benzylic hydrogen is a key to the formation of a p-allyl Pd intermediate and the anti-Markovnikov addition of H2O. The subsequent b-H elimination and tautomerization contribute to the formation of aldehyde products. Water-soluble Pd nanoparticles are characterized using nuclear magnetic resonance (NMR), UV-vis spectroscopy, thermogravimetric analysis (TGA), and transmission electron microscopy (TEM). Catalysis results are examined using 1H NMR and/or GC-MS analyses of isolated reaction mixtures.

| S-EPMC9866704 | biostudies-literature

5-Meth-oxy-N,N-di-n-propyl-tryptamine (5-MeO-DPT): freebase and fumarate.

Project description:The solid-state structures of the synthetic psychedelic 5-meth-oxy-N,N-di-n-propyl-tryptamine (5-MeO-DPT) {systematic name: N-[2-(5-meth-oxy-1H-indol-3-yl)eth-yl]-N-propyl-propan-1-amine}, C17H25N2O, and its fumarate salt, bis-(5-meth-oxy-N,N-di-n-propyl-tryptammonium) fumarate (systematic name: bis-{N-[2-(5-meth-oxy-1H-indol-3-yl)eth-yl]-N-propyl-propan-1-aminium} but-2-ene-dio-ate), 2C17H25N2O+·C4H2O4 2-, are reported. The freebase has a single tryptamine mol-ecule in the asymmetric unit. The mol-ecules are linked together by N-H⋯N hydrogen bonds in zigzag chains along the [010] direction. The fumarate salt has a single tryptammonium cation and half of a fumarate dianion in the asymmetric unit. The tryptammonium and fumarate ions are held together in one-dimensional chains by a series of N-H⋯O hydrogen bonds. These chains are combinations of R 4 4(22) rings, and C 2 2(14) and C 4 4(28) parallel chains along [001].

| S-EPMC8100262 | biostudies-literature

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Selection of a Water-Soluble Salt Form of a Preclinical Candidate, IIIM-290: Multiwell-Plate Salt Screening and Characterization.

Project description:IIIM-290, a semisynthetic derivative of natural product rohitukine, is an orally bioavailable Cdk inhibitor, efficacious in the xenograft models of colon, pancreatic, and leukemia cancer. Its low aqueous solubility (∼8.6 μg/mL) could be one of the reasons for achieving optimal in vivo efficacy relatively at a higher dose. Being a nitrogenous compound, salt formation was envisaged as one of the ideal approaches to enhance its solubility and dissolution profile. Thus, herein, a solubility-guided miniaturized 96-well plate salt screening protocol was devised for identification of the suitable salt form of this preclinical candidate. The solubility-guided strategy has resulted in the identification of hydrochloride as the most favorable counterion, resulting in 45-fold improvement in aqueous solubility. The HCl salt was then scaled up at a gram size and characterized using 1H and 13C NMR, scanning electron microscopy, powder X-ray diffraction, Fourier-transform infrared, and differential scanning calorimetry studies. The HCl salt displayed enhancement in the in vitro dissolution profile as well as improved plasma exposure in the pharmacokinetic study. The oral administration of the IIIM-290·HCl salt in BALB/c mice resulted in >1.5-fold improvement in areas under the curve, Cmax, and half-life. The prepared salt also did not alter its cyclin-dependent kinase (Cdk)-2 and Cdk-9 inhibition activity. This biopharmaceutically improved lead has a potential to investigate further in preclinical studies. The solubility-guided salt screening strategy implemented herein could be utilized for other preclinical leads.

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Bis(?-N,N-di-allyl-dithio-carbamato)bis[(N,N-di-allyl-dithio-carbamato)cadmium].

Project description:The title compound, [Cd2(C7H10NS2)4], is a neutral dinuclear cadmium(II) complex bearing four bis N,N-di-allyl-di-thio-carbamate ligands coordinating to two CdII cations. In each of the monomeric subunits, there are four S atoms of two di-thio-carbamate ligands [Cd-S = 2.5558?(3), 2.8016?(3), 2.6050?(3) and 2.5709?(3)?Å] that coordinate to one CdII atom in a bidentate mode. The dimers are located over an inversion centre bridged by two additional bridging Cd-S bonds [2.6021?(3)?Å], leading to a substantial distortion of the geometry of the monomeric subunit from the expected square-planar geometry. The five-coordinate environment around each of the CdII ions in the dimer is best described as substanti-ally tetra-gonally distorted square pyramidal. The di-thio-carbamate groups are themselves planar and are also coplanar with the CdII ions. The negative charge on these groups is delocalized by resonance across the S atoms bound to the CdII cation. This delocalization of the ? electrons in the di-thio-carbamate groups also extends to the C-N bonds as they reveal significant double bond character [C-N = 1.3213?(16) and 1.3333?(15)?Å].

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Water-Soluble Polymer

Project description:Water-Soluble Polymer Raw sequence reads

| PRJNA1039989 | ENA

1-Allyl-3,3-di-p-tolyl-indolin-2-one.

Project description:In the title compound, C(25)H(23)NO, the indoline system is essentially planar. The mol-ecular structure is stabilized by weak intra-molecular C-H⋯N inter-actions and the crystal packing is determined by inter-molecular C-H⋯π inter-actions.

| S-EPMC2961180 | biostudies-literature

Crystal structures of 3,6-di-allyl-tetra-cyclo[6.3.0.0(4,11).0(5,9)]undeca-2,7-dione and 1,7-di-allyl-penta-cyclo-[5.4.0.0(2,6). 0(3,10).0(5,9)]undecane-8,11-dione: allyl-ated caged compounds.

Project description:The title compounds, C17H20O2 (1) and C17H18O2 (2), are allyl-ated caged compounds. In (1), the carbon atoms bearing the allyl groups are far apart [2.9417?(17)?Å], hence the expected ring-closing metathesis (RCM) protocol failed to give a ring-closing product. When these carbon atoms are connected by a C-C bond as in (2), the distance between them is much smaller [1.611?(3)?Å] and consequently the RCM process was successful. The caged carbon skeleton of (1) can be described as a fusion of four five-membered rings and one six-membered ring. All four five-membered rings exhibit envelope conformations. The structure of compound (2) consists of four five-membered rings, of which two are cyclo-penta-none rings bonded at the 2, 4 and 5 positions and linked at the 3-carbons by a methyl-ene bridge. It also consists of one four-membered and two six-membered rings. All four five-membered rings adopt envelope conformations. In the crystal of (1), mol-ecules are linked via C-H?O hydrogen bonds, forming sheets lying parallel to (010). In the crystal of (2), mol-ecules are linked via C-H?O hydrogen bonds forming chains along [100].

| S-EPMC4257271 | biostudies-literature

Redetermination of the salt hexa-methyl-ene-tetra-minium fumarate.

Project description:THE CRYSTAL STRUCTURE OF THE TITLE COMPOUND [SYSTEMATIC NAME: 3,5,7-triaza-1-azoniatricyclo-[3.3.1.1(3,7)]decane (E)-3-carb-oxy-prop-2-enoate], C(6)H(13)N(4) (+)·C(4)H(3)O(4) (-), had been determined previously by Bowes et al. [Acta Cryst. (2003), B59, 100-117]. Their structure contained an approximately 3:1 ratio of fumarate and succinate monoanions disordered over the same position. The succinate anion component forms a similar structural role to the fumarate anion and came about due to an impurity in the starting material, fumaric acid. In this work, the crystal structure of the pure salt is presented, which is identical, apart from the lack of disorder of the anions, to the previous structure. In the crystal, the ions assemble in the solid state, forming chains via N(+)-H?O(-) and O-H?O(-) hydrogen bonds, which are linked into a three-dimensional network by C-H?O inter-actions.

| S-EPMC3050185 | biostudies-literature

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