Tag: 100-200

《Improved Multigram Route to a Tricyclic Key Intermediate for Dibenzosuberone-Based p38 Inhibitors via an Optimized Early-Stage Heck Coupling》 was written by Forster, Michael; Wentsch-Teltschik, Heike K.; Laufer, Stefan A.. Electric Literature of C7H6Cl2 And the article was included in Organic Process Research & Development on August 20 ,2021. The article conveys some information:

The p38α MAP kinase has been a heavily investigated target in the last two decades. The structural class of dibenzosuberone-based p38 inhibitors, exemplified by the promising candidate skepinone-L, was already successfully validated in several in vivo models of inflammatory as well as oncol. indications. The increasing demand of key intermediates and final compounds caused by the ongoing development of this inhibitor class urged the conception of an optimized route for the preparation of the core dibenzosuberone scaffold in multigram quantities. Rerouting of the initial discovery route resulted in an almost 4-fold increase of overall yield to 46%, the elimination of chromatog. purification, and the substitution of two critical reaction steps, which hindered a feasible scale-up. The key modification was the introduction and optimization of an early-stage Heck coupling based on Buchwald precatalysts allowing consistently high yields (ca. 90%) at multigram scales with a favorably low Pd loading of 0.1 mol %. This newly developed synthetic access to the dibenzosuberone intermediate 2-chloro-7-hydroxy-10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-one is capable of ensuring the supply of skepinone-L and other candidates during further development. In the experimental materials used by the author, we found 3-Chlorobenzylchloride(cas: 620-20-2Electric Literature of C7H6Cl2)

3-Chlorobenzylchloride(cas: 620-20-2) has been used in the reaction of 3-methoxybenzyl chloride and ethyl 4-bromobenzoate in pure water, using zinc dust and a Pd catalyst.Electric Literature of C7H6Cl2

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

《Design, synthesis and biological evaluation of benzo[d]thiazole with dimethylpyrazole derivatives》 was published in Asian Pacific Journal of Cancer Prevention in 2019. These research results belong to Liu, Dachuan; Cheng, Xiu; Wang, Ying. Synthetic Route of C7H6Cl2 The article mentions the following:

A series of new benzothiazole derivatives containing dimethylpyrazole I [R = H, n-pentyl, benzyl, etc.] were synthesized and evaluated for their anticonvulsant activity, neurotoxicity and cytotoxicity by using the maximal electroshock (MES), rotarod neurotoxicity (TOX) and MTT colorimetric assay. Among the compounds studied, four compounds I [R = Bu, n-pentyl, 2-fluorobenzyl, 2,6-dichlorobenzyl] showed better anticonvulsant than the others at 300 mg/kg and they also showed anticonvulsant activity at the dose of 100 mg/kg. All the synthetic compounds I showed lower neurotoxicity and little cytotoxicity, so that the compounds, which with better activities, also had higher protective index. In particular, the compound I [R = 2-fluorobenzyl] showed better activity with an ED50 value of 160.4 mg/kg and higher protective index (PI) values of 2.74 in the MES test than the standard drugs sodium valproate, which used as pos. controls in this study. After that the compound I [R = 2-fluorobenzyl] demonstrated antagonistic activity against seizures induced by pentylenetetrazol, which proved compound I [R = 2-fluorobenzyl] may be exert activity through effecting GABAergic neurotransmission. After reading the article, we found that the author used 3-Chlorobenzylchloride(cas: 620-20-2Synthetic Route of C7H6Cl2)

3-Chlorobenzylchloride(cas: 620-20-2) has been used in the reaction of 3-methoxybenzyl chloride and ethyl 4-bromobenzoate in pure water, using zinc dust and a Pd catalyst.Synthetic Route of C7H6Cl2

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

In 2022,Zhuo, Junming; Zhu, Chunlin; Wu, Jinbao; Li, Zijian; Li, Chao published an article in Journal of the American Chemical Society. The title of the article was 《Reductive Radical Annulation Strategy toward Bicyclo[3.2.1]octanes: Synthesis of ent-Kaurane and Beyerane Diterpenoids》.Product Details of 5781-53-3 The author mentioned the following in the article:

Here, the authors report a general [3+2] radical annulation that allows the facile construction of bicyclo[3.2.1]octane motifs in ent-kaurane- and beyerane-type diterpenoids. This radical annulation is difficult to control but was realized by harnessing an unprecedented and counterintuitive effect of TEMPO. Eleven natural products with a wide array of oxidation states were easily prepared, demonstrating the powerful utility of this straightforward synthetic strategy. In the experiment, the researchers used many compounds, for example, Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3Product Details of 5781-53-3)

Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3) belongs to acyl chlorides. In the laboratory, acyl chlorides are generally prepared by treating carboxylic acids with thionyl chloride (SOCl2). The reaction is catalyzed by dimethylformamide and other additives.Product Details of 5781-53-3

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 66662-48-4On March 31, 2004, Dyadyuchenko, L. V.; Strelkov, V. D.; Mikhailichenko, S. N.; Zaplishny, V. N. published an article in Chemistry of Heterocyclic Compounds. The article was 《Synthesis of some halogen- and nitro-substituted nicotinic acids and their fragmentation under electron impact》. The article mentions the following:

Features of electrophilic and nucleophilic substitution under chlorination and nitration reaction conditions have been investigated for 6-hydroxy- and 6-methyl-3-cyano-4-methyl-2(1H)-pyridones. The polychloro- and nitro-substituted 3-cyano-4-methylpyridines obtained were used as synthons in the synthesis of some polyhalo- and nitro-substituted nicotinic acids and their amides. The fragmentation pathways of the synthesized compounds under electron impact have been studied. In the part of experimental materials, we found many familiar compounds, such as 2-Chloro-4,6-dimethylnicotinic acid(cas: 66662-48-4Related Products of 66662-48-4)

2-Chloro-4,6-dimethylnicotinic acid(cas: 66662-48-4) belongs to pyridine. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. As ligands, solvents, and catalysts they facilitate reactions; thus descriptions of these new ligands and their applications abound each year.Related Products of 66662-48-4

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

In 2022,Zhu, Jian-Jun; Wang, Pei-Yi; Long, Zhou-Qing; Xiang, Shu-Zhen; Zhang, Jun-Rong; Li, Zhen-Xing; Wu, Yuan-Yuan; Shao, Wu-Bin; Zhou, Xiang; Liu, Li-Wei; Yang, Song published an article in Journal of Agricultural and Food Chemistry. The title of the article was 《Design, Synthesis, and Biological Profiles of Novel 1,3,4-Oxadiazole-2-carbohydrazides with Molecular Diversity》.Application of 5781-53-3 The author mentioned the following in the article:

To unceasingly expand the mol. diversity of 1,3,4-oxadiazole-2-carbohydrazides, herein small fragments (including -CH2-, -OCH2-, and -SCH2-) were incorporated into the target compounds I (R = Ph, 2-chlorophenyl, 4-methylphenyl, etc.; R1 = Ph, 2-fuorophenyl, 4-methoxyphenyl, etc.) to screen out the potential succinate dehydrogenase inhibitors (SDHIs). The bioassay results showed that the antifungal effects (expressed by EC50) against Sclerotinia sclerotiorum, Botryosphaeria dothidea, Fusarium oxysporum, and Colletotrichun higginsianum could reach 1.29 I (R = 3-fluorophenyl, R1 = 2-chlorophenyl), 0.63 I (R = Ph, R1 = 4-methylphenyloxy), 1.50 I (R = 3-fluorophenyl, R1 = 4-fluorophenyloxy), and 2.09 I (R = 3-fluorophenyl, R1 = 4-fluorophenyloxy) μg/mL, resp., which were slightly lower than those of carbendazim (EC50 were 0.69, 0.13, 0.55, and 0.80μg/mL, resp.). Especially, compound I (R = 3-fluorophenyl, R1 = 4-methylphenyloxy) was extremely bioactive against Gibberella zeae (G. z.) with an EC50 value of 0.45μg/mL. This outcome was better than that of fluopyram (3.76μg/mL) and was similar to prochloraz (0.47μg/mL). In vivo trials against the corn scab (infected by G. z.) showed that compound I (R = 3-fluorophenyl, R1 = 4-methylphenyloxy) had control activity of 86.8% at 200μg/mL, which was better than that of boscalid (79.6%). Further investigations found that compound I (R = 3-fluorophenyl, R1 = 4-methylphenyloxy) could inhibit the enzymic activity of SDH in the G. z. strain with an IC50 value of 3.67μM, indicating that potential SDHIs might be developed. Addnl., the other biol. activities of these mols. were screened simultaneously. The anti-oomycete activity toward Phytophthora infestans afforded a minimal EC50 value of 3.22μg/mL I (R = 3-fluorophenyl, R1 = 4-methylphenyloxy); compound I (R = 4-fluorophenyl, R1 = phenyl) could strongly suppress the growth of bacterial strains Xanthomonas axonopodis pv. citri and Xanthomonas oryzae pv. oryzae with EC50 values of 3.79 and 11.4μg/mL, resp.; and compound I (R = 3-fluorophenyl, R1 = 2-chlorophenyl) displayed some insecticidal activity toward Plutella xylostella. Given their multipurpose features, these frameworks could be actively studied as potential pesticide leads. In the experimental materials used by the author, we found Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3Application of 5781-53-3)

Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3) belongs to acyl chlorides. Lacking the ability to form hydrogen bonds, acyl chlorides have lower boiling and melting points than similar carboxylic acids. For example, acetic acid boils at 118 °C, whereas acetyl chloride boils at 51 °C. Like most carbonyl compounds, infrared spectroscopy reveals a band near 1750 cm−1.Application of 5781-53-3

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reijneveld, Josephine F.; Marino, Laura; Cao, Thinh-Phat; Cheng, Tan-Yun; Dam, Dennis; Shahine, Adam; Witte, Martin D.; Filippov, Dmitri V.; Suliman, Sara; van der Marel, Gijsbert A.; Moody, D. Branch; Minnaard, Adriaan J.; Rossjohn, Jamie; Codee, Jeroen D. C.; Van Rhijn, Ildiko published an article in 2021. The article was titled 《Rational design of a hydrolysis-resistant mycobacterial phosphoglycolipid antigen presented by CD1c to T cells》, and you may find the article in Journal of Biological Chemistry.COA of Formula: C3H3ClO3 The information in the text is summarized as follows:

Whereas proteolytic cleavage is crucial for peptide presentation by classical major histocompatibility complex (MHC) proteins to T cells, glycolipids presented by CD1 mols. are typically presented in an unmodified form. However, the mycobacterial lipid antigen mannosyl-β1-phosphomycoketide (MPM) may be processed through hydrolysis in antigen presenting cells, forming mannose and phosphomycoketide (PM). To further test the hypothesis that some lipid antigens are processed, and to generate antigens that lead to defined epitopes for future tuberculosis vaccines or diagnostic tests, we aimed to create hydrolysis-resistant MPM variants that retain their antigenicity. Here, we designed and tested three different, versatile synthetic strategies to chem. stabilize MPM analogs. Crystallog. studies of CD1c complexes with these three new MPM analogs showed anchoring of the lipid tail and phosphate group that is highly comparable to nature-identical MPM, with considerable conformational flexibility for the mannose head group. MPM-3, a difluoromethylene-modified version of MPM that is resistant to hydrolysis, showed altered recognition by cells, but not by CD1c proteins, supporting the cellular antigen processing hypothesis. Furthermore, the synthetic analogs elicited T cell responses that were cross-reactive with nature-identical MPM, fulfilling important requirements for future clin. use. In the experiment, the researchers used Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3COA of Formula: C3H3ClO3)

Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3) belongs to acyl chlorides. In the laboratory, acyl chlorides are generally prepared by treating carboxylic acids with thionyl chloride (SOCl2). The reaction is catalyzed by dimethylformamide and other additives.COA of Formula: C3H3ClO3

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Tian, Yue-E.; Sun, Di; Han, Xiao-Xiao; Yang, Jin-Ming; Zhang, Song; Feng, Nan-Nan; Zhu, Li-Na; Xu, Zhong-Yuan; Che, Zhi-Ping; Liu, Sheng-Ming; Lin, Xiao-Min; Jiang, Jia; Chen, Gen-Qiang published their research in Journal of Asian Natural Products Research in 2021. The article was titled 《Synthesis, anti-oomycete activity and SAR studies of paeonol derivatives》.Computed Properties of C4H3ClO2S2 The article contains the following contents:

Three series of sulfonate derivatives I [R1 = H, OMe; R2 = H, C(O)Me; R3 = Et, Ph, 4-FC6H4, etc.] of paeonol were synthesized and screened in vitro for their anti-oomycete activity against P. capsici, resp. Among all the compounds I [R1 = OMe; R2 = C(O)Me; R3 = 4-Cl-3-O2NC6H3], displayed the best promising and pronounced anti-oomycete activity against P. capsici than zoxamide, with the EC50 values of 24.51 and 26.87 mg/L, resp. The results showed that acetyl and 4-OMe were two necessary groups. The existence of these two sites was closely related to the anti-oomycete activity. Relatively speaking, hydroxyl group was well tolerated, and the results showed that after modification of hydroxyl group with sulfonyl, the anti-oomycete activity was significantly increased. The results came from multiple reactions, including the reaction of Thiophene-2-sulfonyl chloride(cas: 16629-19-9Computed Properties of C4H3ClO2S2)

Thiophene-2-sulfonyl chloride(cas: 16629-19-9) is a member of sulfonyl chlorides. Sulfonyl chlorides are reactive sulfonic acid derivatives similar in properties and reactivity to acid chlorides of carboxylates. The sulfonic acid group, however, is a highly hindered molecule, containing a tetrahedral configuration of substituents. Computed Properties of C4H3ClO2S2

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

《Synthesis of sulfonate derivatives of maltol and their biological activity against Phytophthora capsici and Bursaphelenchus xylophilus in vitro》 was written by Tian, Yue-E.; Sun, Di; Yang, Jin-Ming; Che, Zhi-Ping; Liu, Sheng-Ming; Lin, Xiao-Min; Jiang, Jia; Chen, Gen-Qiang. Reference of Thiophene-2-sulfonyl chloride And the article was included in Journal of Asian Natural Products Research in 2020. The article conveys some information:

Sixteen sulfonate derivatives of maltol were synthesized and screened in vitro for their anti-oomycete and nematicidal activity against Phytophthora capsici and Bursaphelenchus xylophilus, resp. Among all the compounds, , , and exhibited the most promising and pronounced anti-oomycete activity against P. capsici than zoxamide, and the EC50 values of 25.42, 18.44, 23.69, and 27.99 mg/L, resp.; compounds , , , and exhibited potent nematicidal activity with LC50 values ranging from 1 to 2 mg/L, especially and showed the best promising and pronounced nematicidal activity, with LC50 values of 1.1762 and 1.2384 mg/L, resp. The experimental process involved the reaction of Thiophene-2-sulfonyl chloride(cas: 16629-19-9Reference of Thiophene-2-sulfonyl chloride)

Thiophene-2-sulfonyl chloride(cas: 16629-19-9) is a member of sulfonyl chlorides. Sulfonyl chlorides are reactive sulfonic acid derivatives similar in properties and reactivity to acid chlorides of carboxylates. The sulfonic acid group, however, is a highly hindered molecule, containing a tetrahedral configuration of substituents. Reference of Thiophene-2-sulfonyl chloride

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

The author of 《Novel 1,3,4-Oxadiazole-2-carbohydrazides as Prospective Agricultural Antifungal Agents Potentially Targeting Succinate Dehydrogenase》 were Wu, Yuan-Yuan; Shao, Wu-Bin; Zhu, Jian-Jun; Long, Zhou-Qing; Liu, Li-Wei; Wang, Pei-Yi; Li, Zhong; Yang, Song. And the article was published in Journal of Agricultural and Food Chemistry in 2019. COA of Formula: C3H3ClO3 The author mentioned the following in the article:

A novel simple 1,3,4-oxadiazole-2-carbohydrazides was reported to discover low-cost and versatile antifungal agents. Bioassay results suggested that a majority of the designed compounds were extremely bioactive against four types of fungi and two kinds of oomycetes. This extreme bioactivity was highlighted by the applausive inhibitory effects of compounds 4b, 4h, 5c, 5g, 5h, 5i, 5m, 5p, 5t, and 5v against Gibberella zeae, affording EC50 values ranging from 0.486μg/mL to 0.799μg/mL, which were superior to that of fluopyram (2.96μg/mL) and comparable to those of carbendazim (0.947μg/mL) and prochloraz (0.570μg/mL). Meanwhile, compounds 4g, 5f, 5i, and 5t showed significant actions against Fusarium oxysporum with EC50 values of 0.652, 0.706, 0.813, and 0.925μg/mL, resp. Pharmacophore exploration suggested that the N’-phenyl-1,3,4-oxadiazole-2-carbohydrazide pattern is necessary for the bioactivity. Mol. docking of 5h with succinate dehydrogenase (SDH) indicated that it can completely locate the inside of the binding pocket via hydrogen-bonding and hydrophobic interactions, revealing that this novel framework might target SDH. This result was further verified by the significant inhibitory effect on SDH activity. In addition, SEM patterns were performed to elucidate the anti-G. zeae mechanism. Given these features, this type of frameworks is a suitable template for future exploration of alternative SDH inhibitors against plant microbial infections. The results came from multiple reactions, including the reaction of Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3COA of Formula: C3H3ClO3)

Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3) belongs to acyl chlorides. Lacking the ability to form hydrogen bonds, acyl chlorides have lower boiling and melting points than similar carboxylic acids. For example, acetic acid boils at 118 °C, whereas acetyl chloride boils at 51 °C. Like most carbonyl compounds, infrared spectroscopy reveals a band near 1750 cm−1.COA of Formula: C3H3ClO3

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Zhu, Chunfang; Zhang, Meng; Tang, Qiaoling; Yang, Qian; Li, Jing; He, Xuan; Ye, Yong published their research in Journal of Agricultural and Food Chemistry on December 26 ,2019. The article was titled 《Structure and Activity of the Camellia oleifera Sapogenin Derivatives on Growth and Biofilm Inhibition of Staphylococcus aureus and Escherichia coli》.COA of Formula: C7H6Cl2 The article contains the following contents:

Sapogenin is the main block of Camellia oleifera saponin, which was purified and structurally modified by the C28 acylation reaction to synthesize 19 new derivatives The growth and biofilm inhibition of Staphylococcus aureus and Escherichia coli was measured to evaluate their antibacterial effects. A three-dimensional quant. structure-activity relationship (3D-QSAR) assay indicated that the antibacterial activities were significantly enhanced after sapogenin was modified with an aromatic ring or heterocyclic ring and electron-withdrawing substituents at the meta or para position. Among them, the derivative of sapogenin with a 2-mercapto-4-methyl-5-thiazolyl acetyl group obviously destroyed bacterial biofilm and made bacteria lysis. 3D-QSAR provides practical information for the structural design of sapogenin derivatives with strong antibacterial activity, and the C. oleifera sapogenin derivative 28-O-(2-mercapto-4-methyl-5-thiazolyl)-3β,16α,21β,22α-O-tetrahydroxy-oleantel-2-ene-23-aldehyde (S-16) is an effective candidate as an antibacterial agent for the prevention of bacterial resistance against antibiotics. In the part of experimental materials, we found many familiar compounds, such as 3-Chlorobenzylchloride(cas: 620-20-2COA of Formula: C7H6Cl2)

3-Chlorobenzylchloride(cas: 620-20-2) has been used in the reaction of 3-methoxybenzyl chloride and ethyl 4-bromobenzoate in pure water, using zinc dust and a Pd catalyst.COA of Formula: C7H6Cl2

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics