Category: 73303-88-5

Singh, Rajeeva published the artcileComparisons of rate constants for thiolate-disulfide interchange in water and in polar aprotic solvents using dynamic proton NMR line shape analysis, Category: alcohols-buliding-blocks, the publication is Journal of the American Chemical Society (1990), 112(3), 1190-7, database is CAplus.

The rate constants for representative thiolate-disulfide interchange reactions are larger in DMSO and DMF than in water by a factor of ∼2300 at 24°. The log of the rate constant is directly proportional to the mole fraction of D₂O in mixtures of DMSO and D₂O, even at small mole fractions of D₂O. This linear proportionality suggests that thiolate anion is not specifically solvated by water and that hydrogen bonding is relatively unimportant in stabilizing this species. The values of ΔS^⧧ for thiolate-disulfide interchange are ∼-10 cal/(deg mol), presumptively because of loss in the entropy of the reactants in going from ground to transition state, partially compensated by a gain in entropy from solvent release. Introduction of a hydroxy group β to the C-S bond slows the reaction by a factor of 2-15; the introduction of Me groups β to the C-S bond slows the rate by factors of 3-20.

Journal of the American Chemical Society published new progress about 73303-88-5. 73303-88-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Aliphatic hydrocarbon chain,Alcohol, name is 2-Methyl-2-sulfanylpropan-1-ol, and the molecular formula is C23H20BN, Category: alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Sadowsky, Jack D. published the artcileDevelopment of Efficient Chemistry to Generate Site-Specific Disulfide-Linked Protein- and Peptide-Payload Conjugates: Application to THIOMAB Antibody-Drug Conjugates, Quality Control of 73303-88-5, the publication is Bioconjugate Chemistry (2017), 28(8), 2086-2098, database is CAplus and MEDLINE.

Conjugation of small mol. payloads to specific cysteine residues on proteins via a disulfide bond represents an attractive strategy to generate redox-sensitive bioconjugates, which have value as potential diagnostic reagents or therapeutics. Advancement of such “direct-disulfide” bioconjugates to the clinic necessitates chem. methods to form disulfide connections efficiently, without byproducts. The disulfide connection must also be resistant to premature cleavage by thiols prior to arrival at the targeted tissue. We show here that commonly-employed methods to generate direct disulfide-linked bioconjugates are inadequate for addressing these challenges. We describe our efforts to optimize direct-disulfide conjugation chem., focusing on the generation of conjugates between cytotoxic payloads and cysteine-engineered antibodies (i.e., THIOMAB antibody-drug conjugates, or TDCs). This work culminates in the development of novel, high-yielding conjugation chem. for creating direct payload disulfide connections to any of several Cys mutation sites in THIOMAB antibodies or to Cys sites in other biomols. (e.g., human serum albumin and cell-penetrating peptides). We conclude by demonstrating that hindered direct disulfide TDCs with two Me groups adjacent to the disulfide, which have heretofore not been described for any bioconjugate, are more stable and more efficacious in mouse tumor xenograft studies than less hindered analogs.

Bioconjugate Chemistry published new progress about 73303-88-5. 73303-88-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Aliphatic hydrocarbon chain,Alcohol, name is 2-Methyl-2-sulfanylpropan-1-ol, and the molecular formula is C4H10OS, Quality Control of 73303-88-5.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Watson, Christine published the artcileOptimization of a novel series of selective CNS penetrant CB₂ agonists, Formula: C4H10OS, the publication is Bioorganic & Medicinal Chemistry Letters (2011), 21(14), 4284-4287, database is CAplus and MEDLINE.

A series of benzimidazole CB₂ receptor agonists were prepared and their properties investigated. Optimization of the three benzimidazole substituents led to the identification of I [R = cyclopropylmethyl, II], a potent CB₂ full agonist (EC₅₀ 2.7 nM) with excellent selectivity over the CB₁ receptor (>3000-fold). II demonstrated good CNS penetration in rats. Further optimization led to the identification of I [R = (2R)-2-tetrahydrofuranylmethyl] with improved selectivity over hERG and excellent CNS penetration in rat.

Bioorganic & Medicinal Chemistry Letters published new progress about 73303-88-5. 73303-88-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Aliphatic hydrocarbon chain,Alcohol, name is 2-Methyl-2-sulfanylpropan-1-ol, and the molecular formula is C9H20Cl2Si, Formula: C4H10OS.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Reginato, Marcelo Mota published the artcileConformational study of the electronic interactions and nitric oxide release potential of new S-nitrosothiols esters derivatives of ibuprofen, naproxen and phenyl acids substituted (SNO-ESTERS): Synthesis, infrared spectroscopy analysis and theoretical calculations, Synthetic Route of 73303-88-5, the publication is Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy (2019), 132-142, database is CAplus and MEDLINE.

The conformational study on the new S-nitrosothiols esters (SNO-ESTERS): para-substituted (X = H, OMe, Cl and NO₂) S-nitrosothiol derivatives 2-methyl-2-(sulfanyl)propyl phenylacetates (R1), 2-(4-isobutylphenyl)propanoate (ibuprofen, R2), and 2-(4-isobutylphenyl)propanoate of 2-methyl-2-(nitrososulfanyl)propyl (naproxen, R3) was performed using IR spectroscopy (IR) in solvents with increasing polarity (CCl₄, CH₃Cl, and CH₃CN), and theor. calculations, to determine the preferential conformer and the potential of these compounds to release nitric oxide (NO). S-Nitrosothiols were synthesized by esterification reactions, using chlorides of the corresponding carboxylic acids, with good yields (~60%). IR results showed that these compounds presented only one conformation, and the exptl. data were supported by the theor. results obtained by d. functional theory (DFT) calculations using the 6311+G (2df, 2p) basis set. The calculations revealed that all S-nitrosothiols presented one preferential anticlinal (ac) geometric conformation, which agrees with the data obtained exptl. in CCl₄. These conformers are stabilized by intramol. hydrogen bonds. Examination of the geometry with regard to the R-SNO group revealed that these compounds are preferentially in the trans (anti) conformation. The calculation of the orbital interactions using the Natural Bond Orbital (NBO) method showed that the n_O(NO) → σ*_(S-N) hyper-conjugative interaction increases the S-N bond length. The strong nS → π*_(NO) interaction and electronic delocalization induces a partial π character to the S-N bond. The weak σ_S-N bond indicates strong delocalization of the electron pair in O (NO) by the n_O(NO) → σ*_(S-N) interaction, thereby increasing the capacity of NO release from SNO-ESTERS.

Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy published new progress about 73303-88-5. 73303-88-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Aliphatic hydrocarbon chain,Alcohol, name is 2-Methyl-2-sulfanylpropan-1-ol, and the molecular formula is C4H10OS, Synthetic Route of 73303-88-5.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Nicolaou, K. C. published the artcileSynthesis and Biological Evaluation of Shishijimicin A-Type Linker-Drugs and Antibody-Drug Conjugates, Name: 2-Methyl-2-sulfanylpropan-1-ol, the publication is Journal of the American Chemical Society (2020), 142(29), 12890-12899, database is CAplus and MEDLINE.

Our previous studies with shishijimicin A resulted in the total synthesis of this scarce marine natural product and a number of its simpler analogs endowed with picomolar potencies against certain cancer cell lines. Herein, we describe the design, synthesis, and biol. evaluation of four linker-drugs, anticipating the construction of antibody-drug conjugates (ADCs) as the ultimate goal of this research program. Using a common payload, the assembly of these linker-drugs utilized different linkers and attachment points, providing opportunities to probe the optimal mol. design of the intended ADCs as targeted cancer therapies. In the course of ADC generation and in vitro evaluation, we identified two linker-drugs with a promising in vitro plasma stability profile and excellent targeted cytotoxicity and specificity. Conjugation of shishijimicin A enediyne payloads through their phenolic moiety represents a novel approach to enediyne ADC creation, while the pharmacol. profiles of at least two of the generated ADCs compare well with the profiles of the corresponding clin. approved ADC Kadcyla.

Journal of the American Chemical Society published new progress about 73303-88-5. 73303-88-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Aliphatic hydrocarbon chain,Alcohol, name is 2-Methyl-2-sulfanylpropan-1-ol, and the molecular formula is C4H10OS, Name: 2-Methyl-2-sulfanylpropan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Mascharak, P. K. published the artcileStructural distortions of the [Fe₄S₄]²⁺ core of [Fe₄S₄(S-tert-C₄H₉)₄]^2- in different crystalline environments and detection and instability of oxidized ([Fe₄S₄]³⁺) clusters, Name: 2-Methyl-2-sulfanylpropan-1-ol, the publication is Inorganica Chimica Acta (1983), 80(3), 157-70, database is CAplus.

The structural and redox chem. of the clusters [Fe₄S₄(SR)₄]^2- with R = tert-alkyl were investigated for the purpose of determining the structures of the same cluster in different environments and the stability of the oxidized species [Fe₄S₄(SR)₄]^1-. (Me₃NCH₂Ph)₂[Fe₄S₄(S-tert-Bu)₄] crystallizes in the monoclinic space group P2₁/c with no imposed symmetry. (Et₄N)₂[Fe₄S₄(S-tert-Bu)₄] crystallizes in the tetragonal space group I4̅2m with D_2d symmetry imposed on the cluster. The [Fe₄S₄]²⁺ cluster cores in both compounds exhibit compressed tetragonal structures with different extents of distortion from T_d symmetry. These structures are compared to those of other [Fe₄S₄]²⁺ clusters by means of core shape parameters. Clusters with R = tert-alkyl (tert-Bu, C(CH₃)₂CH₂OH, C(CH₃)₂CH₂NHPh) in DMF exhibit, in addition to the usual 2-/3- and 3-/4- redox reactions common to all [Fe₄S₄(SR)₄]^2- species, discrete 1-electron oxidations near -0.1 V vs. SCE. Cyclic voltammetry of [Fe₄S₄(S-tert-Bu)₄]^2- reveals an essentially reversible 1-/2- couple with E_1/2 = -0.12 V, supporting the authenticity of clusters containing an oxidized ([Fe₄S₄]³⁺) core. This couple cannot be electrochem. resolved from multi-electron oxidation in the case of clusters in DMF with other types of R substituents, a behavior apparently due to cathodic potential shifts by tert-alkyl groups. Stability of oxidized clusters is low, and [Fe₄S₄(S-tert-Bu)₄]^1- could not be generated in appreciable concentrations at longer times by coulometric or chem. oxidation The relative stabilities of analog and protein [Fe₄S₄]³⁺ clusters are discussed. Preparations of 4 new [Fe₄S₄(SR)₄]^2- cluster salts are described including water-soluble (Et₄N)₂[Fe₄S₄(SC(CH₃)₂CH₂OH)₄].

Inorganica Chimica Acta published new progress about 73303-88-5. 73303-88-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Aliphatic hydrocarbon chain,Alcohol, name is 2-Methyl-2-sulfanylpropan-1-ol, and the molecular formula is C4H10OS, Name: 2-Methyl-2-sulfanylpropan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Stec, Wojciech J. published the artcileDiastereomers of Nucleoside 3′-O-(2-Thio-1,3,2-oxathia(selena)phospholanes): Building Blocks for Stereocontrolled Synthesis of Oligo(nucleoside phosphorothioate)s, Name: 2-Methyl-2-sulfanylpropan-1-ol, the publication is Journal of the American Chemical Society (1995), 117(49), 12019-29, database is CAplus.

Diastereomerically pure 5′-O-DMT-nucleoside 3′-O-(2-thio-1,3,2-oxathiaphospholanes) I ( B = T, Ade^bz, Cyt^bz) were used for the synthesis of stereo-regular oligo(nucleoside phosphorothioate)s (S-Oligos). The oxathiaphospholane ring-opening condensation requires the presence of strong organic base, preferably DBU. The yield of a single coupling step is ca. 95% and resulting S-Oligos are free of nucleobase- and sugar-phosphorothioate backbone modifications. The diastereomeric purity of products was estimated on the basis of diastereoselective degradation with Nuclease P1 and a mixture of snake venom phosphodiesterase and Serratia marcescens endonuclease. Thermal dissociation studies of hetero-duplexes S-Oligos/DNA and S-Oligos/RNA showed that their stability is stereochem.- and sequence-dependent.

Journal of the American Chemical Society published new progress about 73303-88-5. 73303-88-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Aliphatic hydrocarbon chain,Alcohol, name is 2-Methyl-2-sulfanylpropan-1-ol, and the molecular formula is C5H10Cl3O3P, Name: 2-Methyl-2-sulfanylpropan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Gokel, George W. published the artcileSulfur heterocycles. I. Use of 4,4-dimethyl-1,3-oxathiolane-3,3-dioxide as a carbonyl anion equivalent, Recommanded Product: 2-Methyl-2-sulfanylpropan-1-ol, the publication is Tetrahedron Letters (1979), 3375-8, database is CAplus.

The oxathiolane I (R = H), acting as a carbonyl anion equivalent, was alkylated with BuLi and the appropriate reagent to give I [R = D, Me, PhCH₂, CH₂:CHCH₂, Me(CH₂)₅, 1-hydroxycyclopentyl, 1-hydroxycyclohexyl, 1-hydroxycyclododecyl, PhCH(OH), PhC(OH)Me, Me₃Si, Ph]. Thermal demasking of I (R ≠ H, D), with loss of Me₂C:CH₂ and SO₂, gave the corresponding aldehyde or α-silyl ketone. E.g., pyrolysis of I (R = PhCH₂) gave 100% PhCH₂CHO.

Tetrahedron Letters published new progress about 73303-88-5. 73303-88-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Aliphatic hydrocarbon chain,Alcohol, name is 2-Methyl-2-sulfanylpropan-1-ol, and the molecular formula is C4H10OS, Recommanded Product: 2-Methyl-2-sulfanylpropan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Gokel, George W. published the artcileSulfur heterocycles. 3. Heterogeneous, phase-transfer, and acid-catalyzed potassium permanganate oxidation of sulfides to sulfones and a survey of their carbon-13 nuclear magnetic resonance spectra, Name: 2-Methyl-2-sulfanylpropan-1-ol, the publication is Journal of Organic Chemistry (1980), 45(18), 3634-9, database is CAplus.

Nineteen low-mol.-weight and heterocyclic sulfides were oxidized by variations of a technique using KMnO₄ and various catalysts. In addition, the NMR spectra of these compounds and other sulfones are reported.

Journal of Organic Chemistry published new progress about 73303-88-5. 73303-88-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Aliphatic hydrocarbon chain,Alcohol, name is 2-Methyl-2-sulfanylpropan-1-ol, and the molecular formula is C4H10OS, Name: 2-Methyl-2-sulfanylpropan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Kreevoy, Maurice M. published the artcileEffect of structure on mercaptan dissociation constants, HPLC of Formula: 73303-88-5, the publication is Journal of Organic Chemistry (1964), 29(6), 1641-2, database is CAplus.

A redetn. of the K_A for PhSH, and also a number of other K_A values, some new and some redtd., were reported. It was concluded that there was no Baker-Nathan effect, but that there was a resonance exaltation of mercaptan dissociation constants of ∼1.3 log units for conjugated mercaptans. These results were given in a table for RSH when R was as follows: Ac, Ph, (2-pyridyl)methyl, EtO₂CCH₂CH₂, HOCH₂CMe₂ Me, tert-Bu, and tert-Am. These results were discussed.

Journal of Organic Chemistry published new progress about 73303-88-5. 73303-88-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Aliphatic hydrocarbon chain,Alcohol, name is 2-Methyl-2-sulfanylpropan-1-ol, and the molecular formula is C4H10OS, HPLC of Formula: 73303-88-5.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts