Tag: M.W=100-150

Berecz, Gabor published the artcileTowards Tianeptine Analogues: Synthesis of New Ring Systems Containing a Dibenzo[c,f[1,2]thiazepine S,S -Dioxide Core, Quality Control of 622-40-2, the publication is Synthesis (2022), 54(17), 3874-3882, database is CAplus.

In the course of the synthesis of fused-ring analogs of the antidepressant drug tianeptine, representatives of three new heterocyclic ring systems, indolo[1,7- bc][1,2]benzothiazepines (and their 4,5-dihydro analogs), 5,6-dihydroquino[1,8- bc][1,2]benzothiazepine, and [1,2]benzothiazepino[4,3,2- jk]carbazoles, as well as their intermediates, was prepared The tetracyclic and pentacyclic ring systems containing either an oxo or a hydroxy functional group are suitable for introducing various side chains, including potential pharmacophores. For this latter transformation, examples are demonstrated by conversion of the hydroxy group into a chloro moiety and subsequent reaction with amines or with primary alcs. bearing a tertiary amino side chain. Two fused-ring derivatives exhibiting the side-chain characteristics of tianeptine was also synthesized. Altogether 40 compounds were described in the present manuscript, eight of them are also characterized by single-crystal X-ray diffraction.

Synthesis published new progress about 622-40-2. 622-40-2 belongs to alcohols-buliding-blocks, auxiliary class Morpholine,Alcohol, name is 2-Morpholinoethanol, and the molecular formula is C6H13NO2, Quality Control of 622-40-2.

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

Chen, Xingmei published the artcileMachine learning-based prediction of toxicity of organic compounds towards fathead minnow, Quality Control of 622-40-2, the publication is RSC Advances (2020), 10(59), 36174-36180, database is CAplus and MEDLINE.

Predicting the acute toxicity of a large dataset of diverse chems. against fathead minnows (Pimephales promelas) is challenging. In this paper, 963 organic compounds with acute toxicity towards fathead minnows were split into a training set (482 compounds) and a test set (481 compounds) with an approx. ratio of 1 : 1. Only six mol. descriptors were used to establish the quant. structure-activity/toxicity relationship (QSAR/QSTR) model for 96 h pLC₅₀ through a support vector machine (SVM) along with genetic algorithm. The optimal SVM model (R² = 0.756) was verified using both internal (leave-one-out cross-validation) and external validations. The validation results (q_int² = 0.699 and q_ext² = 0.744) were satisfactory in predicting acute toxicity in fathead minnows compared with other models reported in the literature, although our SVM model has only six mol. descriptors and a large data set for the test set consisting of 481 compounds

RSC Advances published new progress about 622-40-2. 622-40-2 belongs to alcohols-buliding-blocks, auxiliary class Morpholine,Alcohol, name is 2-Morpholinoethanol, and the molecular formula is C6H13NO2, Quality Control of 622-40-2.

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

Uddin, Jashim Md. published the artcileDesign, Synthesis, and Structure-Activity Relationship Studies of Fluorescent Inhibitors of Cycloxygenase-2 as Targeted Optical Imaging Agents, Computed Properties of 14703-69-6, the publication is Bioconjugate Chemistry (2013), 24(4), 712-723, database is CAplus and MEDLINE.

Cyclooxygenase-2 (COX-2) is an attractive target for mol. imaging because it is an inducible enzyme that is expressed in response to inflammatory and proliferative stimuli. Recently, the authors reported that conjugation of indomethacin with carboxy-X-rhodamine dyes results in the formation of effective, targeted, optical imaging agents able to detect COX-2 in inflammatory tissues and premalignant and malignant tumors. The present paper summarizes the details of the structure-activity relationship (SAR) studies performed for lead optimization of these dyes. A wide range of fluorescent conjugates were designed and synthesized, and each of them was tested for the ability to selectively inhibit COX-2 as the purified protein and in human cancer cells. The SAR study revealed that indomethacin conjugates are the best COX-2-targeted agents compared to the other carboxylic acid-containing nonsteroidal anti-inflammatory drugs (NSAIDs) or COX-2-selective inhibitors (COXIBs). An n-butyldiamide linker is optimal for tethering bulky fluorescent functionalities onto the NSAID or COXIB cores. The activity of conjugates also depends on the size, shape, and electronic properties of the organic fluorophores. These reagents are taken up by COX-2-expressing cells in culture, and the uptake is blocked by pretreatment with a COX inhibitor. In in vivo settings, these reagents become highly enriched in COX-2-expressing tumors compared to surrounding normal tissue, and they accumulate selectively in COX-2-expressing tumors as compared with COX-2-neg. tumors grown in mice. Thus, COX-2-targeted fluorescent inhibitors are useful for preclin. and clin. detection of lesions containing elevated levels of COX-2.

Bioconjugate Chemistry published new progress about 14703-69-6. 14703-69-6 belongs to alcohols-buliding-blocks, auxiliary class Amine,Benzene,Phenol, name is 3-(Methylamino)phenol, and the molecular formula is C4H5NS2, Computed Properties of 14703-69-6.

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

Lyons, Amanda Jane published the artcileScaling up a C-H Borylation: Addressing the Safety Concerns of an Iridium-Catalyzed Process for Multikilo Scale Manufacture, Category: alcohols-buliding-blocks, the publication is Organic Process Research & Development (2022), 26(5), 1378-1388, database is CAplus.

Ir-catalyzed C-H borylation reactions are a rapid and versatile entry into Suzuki coupling partners, but their inherent safety issues can limit their use in large-scale manufacture The stoichiometric byproduct from this reaction, HBpin, can liberate H gas on contact with moisture in air, as well as acting as an effective borylating agent in the reaction, resulting in an addnl. pathway for the generation of H. Using a targeted, multidisciplinary approach, a C-H borylation process to generate a key intermediate in the synthesis of an API was redesigned in preparation for large-scale manufacture Through careful evaluation of the existing process and the use of high-throughput experimentation, PAT techniques, NMR, process safety experimentation, and process engineering, the process was constructed so that inherent risks associated with this reaction were minimized and contained to a final controlled quench of the reactive byproducts of the reaction. The final process was transferred to a manufacturing facility, delivering >70 kg of the borylated product over two batches.

Organic Process Research & Development published new progress about 25240-59-9. 25240-59-9 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester,Boronic Acids,Boronate Esters, name is 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, and the molecular formula is C6H13BO3, Category: alcohols-buliding-blocks.

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

Pozo, Iago published the artcileToward 2-Thiophyne: Ketocarbene versus Hetaryne Intermediates from 2-(Trimethylsilyl)thiophen-3-yl Triflate, Synthetic Route of 17236-59-8, the publication is Organic Letters (2021), 23(19), 7376-7380, database is CAplus and MEDLINE.

The reaction of 2-(trimethylsilyl)thiophen-3-yl triflate with CsF in the presence of 2,3,4,5-tetraphenylcyclopentadienone affords 4,5,6,7-tetraphenylbenzo[b]thiophene, as it would be expected from the hypothesized generation and trapping of 2-thiophyne. However, a detailed exptl. and computational study discards the intermediacy of this elusive 5-membered hetaryne. Instead, a complex mechanism involving the generation of an intermediate ketocarbene, which adds to the cyclopentadienone to give an isolable tricyclic intermediate, followed by thermal rearrangements, is proposed.

Organic Letters published new progress about 17236-59-8. 17236-59-8 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Alcohol, name is Thiophen-3-ol, and the molecular formula is C4H4OS, Synthetic Route of 17236-59-8.

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

Tota, Arianna published the artcileN-N Bond Formation Using an Iodonitrene as an Umpolung of Ammonia: Straightforward and Chemoselective Synthesis of Hydrazinium Salts, Related Products of alcohols-buliding-blocks, the publication is Advanced Synthesis & Catalysis (2021), 363(1), 194-199, database is CAplus.

The formation of hydrazinium salts by N-N bond formation has typically involved the use of hazardous and difficult to handle reagents. Here, mild and operationally simple conditions for the synthesis of hydrazinium salts are reported. Electrophilic nitrogen transfer to the nitrogen atom of tertiary amines is achieved using iodosylbenzene as oxidant and ammonium carbamate as the N-source. The resulting process is highly chemoselective and tolerant to other functional groups. A wide scope is reported, including examples with bioactive mols. Insights on the structure of hydrazinium salts were provided by X-ray anal.

Advanced Synthesis & Catalysis published new progress about 622-40-2. 622-40-2 belongs to alcohols-buliding-blocks, auxiliary class Morpholine,Alcohol, name is 2-Morpholinoethanol, and the molecular formula is C5H6BNO2, Related Products of alcohols-buliding-blocks.

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

Viger, Mathieu L. published the artcileDistinct ON/OFF fluorescence signals from dual-responsive activatable nanoprobes allows detection of inflammation with improved contrast, Safety of 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, the publication is Biomaterials (2017), 119-131, database is CAplus and MEDLINE.

Visualization of biochem. changes associated with disease is of great clin. significance, as it should allow earlier, more accurate diagnosis than structural imaging, facilitating timely clin. intervention. Herein, we report combining stimuli-responsive polymers and near-IR fluorescent dyes (emission max: 790 nm) to create robust activatable fluorescent nanoprobes capable of simultaneously detecting acidosis and oxidative stress associated with inflammatory microenvironments. The spectrally-resolved mechanism of fluorescence activation allows removal of unwanted background signal (up to 20-fold reduction) and isolation of a pure activated signal, which enables sensitive and unambiguous localization of inflamed areas; target-to-background ratios reach 22 as early as 3 h post-injection. This new detection platform could have significant clin. impact in early detection of pathologies, individual tailoring of drug therapy, and image-guided tumor resection.

Biomaterials published new progress about 25240-59-9. 25240-59-9 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester,Boronic Acids,Boronate Esters, name is 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, and the molecular formula is C17H14N2O2, Safety of 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol.

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

Amery, G. W. published the artcileSynthesis and identification of some N-methylated aminonitrophenols, Application In Synthesis of 14703-69-6, the publication is Journal of the Chemical Society [Section] C: Organic (1967), 1053-7, database is CAplus.

The synthesis of a number of new N-methyl and N,N-dimethylaminonitrophenols is described. Spectroscopy assisted in deducing the orientation of these compounds In particular, the position of the nitro group, relative to the OH group, can be clearly discerned by comparison of the spectrum of the hydroxynitroanilinium ion with those of the 3 nitrophenols. 26 references.

Journal of the Chemical Society [Section] C: Organic published new progress about 14703-69-6. 14703-69-6 belongs to alcohols-buliding-blocks, auxiliary class Amine,Benzene,Phenol, name is 3-(Methylamino)phenol, and the molecular formula is C7H9NO, Application In Synthesis of 14703-69-6.

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

Cao, Sheng published the artcileSubstituent Effects on Oxidation-Induced Formation of Quinone Methides from Arylboronic Ester Precursors, Application In Synthesis of 25240-59-9, the publication is Chemistry – A European Journal (2013), 19(27), 9050-9058, database is CAplus and MEDLINE.

A series of arylboronic esters containing different aromatic substituents and various benzylic leaving groups (Br or N⁺Me₃Br^–) have been synthesized. The substituent effects on their reactivity with H₂O₂ and formation of quinone methide (QM) have been investigated. NMR spectroscopy and Et vinyl ether (EVE) trapping experiments were used to determine the reaction mechanism and QM formation, resp. QMs were not generated during oxidative cleavage of the boronic esters but by subsequent transformation of the phenol products under physiol. conditions. The oxidative deboronation is facilitated by electron-withdrawing substituents, such as aromatic F, NO₂, or benzylic N⁺Me₃Br^–, whereas electron-donating substituents or a better leaving group favor QM generation. Compounds containing an aromatic CH₃ or OMe group, or a good leaving group (Br), efficiently generate QMs under physiol. conditions. Finally, a quant. relationship between the structure and activity has been established for the arylboronic esters by using a Hammett plot. The reactivity of the arylboronic acids/esters and the inhibition or facilitation of QM formation can now be predictably adjusted. This adjustment is important as some applications may benefit and others may be limited by QM generation.

Chemistry – A European Journal published new progress about 25240-59-9. 25240-59-9 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester,Boronic Acids,Boronate Esters, name is 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, and the molecular formula is C6H13BO3, Application In Synthesis of 25240-59-9.

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

Lemke, Carina published the artcileChromenones as Multineurotargeting Inhibitors of Human Enzymes, Synthetic Route of 622-40-2, the publication is ACS Omega (2019), 4(26), 22161-22168, database is CAplus and MEDLINE.

The complex nature of multifactorial diseases, such as Morbus Alzheimer, has produced a strong need to design multitarget-directed ligands to address the involved complementary pathways. A purposive structural modification of a tetratarget small-mol. contilisant and generated a combinatorial library of substituted chromen-4-ones I (R = pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl, etc.; n = 2, 3, 4, 5) is reported. The compounds comprise a basic moiety which is linker-connected to the 6-position of the heterocyclic chromenone core. The syntheses were accomplished by Mitsunobu- or Williamson-type ether formations. The resulting library members were evaluated at a panel of seven human enzymes, all of which being involved in the pathophysiol. of neurodegeneration. A concomitant inhibition of human acetylcholinesterase and human monoamine oxidase B, with IC50 values of 5.58 and 7.20 μM, resp., was achieved with the dual-target 6-(4-(piperidin-1-yl)butoxy)-4H-chromen-4-one.

ACS Omega published new progress about 622-40-2. 622-40-2 belongs to alcohols-buliding-blocks, auxiliary class Morpholine,Alcohol, name is 2-Morpholinoethanol, and the molecular formula is C6H13NO2, Synthetic Route of 622-40-2.

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