1-(2,3-二氢-4-甲基-2-硫氧代-5-噻唑)-乙酮 | 7725-93-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2,3-二氢-4-甲基-2-硫氧代-5-噻唑)-乙酮
• 英文名称: 5-acetyl-2-mercapto-4-methylthiazole
• 英文别名: 4-methyl-5-(1-oxoethyl)-2-mercaptothiazole；2-Mercapto-4-methyl-5-thiazolyl methyl ketone；1-(4-methyl-2-sulfanylidene-3H-1,3-thiazol-5-yl)ethanone
• CAS: 7725-93-1
• 化学式: C₆H₇NOS₂
• mdl: MFCD11499365
• 分子量: 173.26
• InChiKey: CVQAKSAYAODIKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  86.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  1-(2,3-二氢-4-甲基-2-硫氧代-5-噻唑)-乙酮 在 ammonium peroxydisulfate 作用下， 生成 PH002090
  参考文献：
  名称：

  Thiazolethiols and their Derivatives

  摘要：

  DOI：

  10.1021/ja01097a029
• 作为产物：
  描述：

  5-乙酰基-2-氨基-4-甲基噻唑 在 氢溴酸 、 硫脲 、 sodium nitrite 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 6.0h， 生成 1-(2,3-二氢-4-甲基-2-硫氧代-5-噻唑)-乙酮
  参考文献：
  名称：

  Mnk2和FLT3的双重抑制潜在治疗急性髓细胞性白血病

  摘要：

  迫切需要发现新型抗AML治疗药物，但该疾病复杂的异质性迄今阻碍了治疗方法的发展。FLT3抑制剂已在临床试验中显示出治疗潜力。但单药疗法已与由并行信号通路（包括MAPK和mTOR）激活介导的耐药性相关。因此，抑制两个信号通路的联系以及抑制FLT3可能是有利的。在本文中，我们建议与单独靶向FLT3相比，对FLT3和Mnk的双重抑制将为AML患者提供更好的临床选择。因此，一系列的N-苯基-4-（噻唑-5-基）嘧啶-2-胺和4-（吲哚-3-基）-N制备了-苯基嘧啶-2-胺。确定了有效的Mnk2抑制剂，FLT3抑制剂以及Mnk2和FLT3的双重抑制剂，并评估了它们对MV4-11 AML细胞系的抗增殖活性。与单独抑制FLT3或Mnk2相比，对FLT3和Mnk2的双重抑制导致MV4-11细胞凋亡的细胞死亡增加。

  DOI：

  10.1016/j.ejmech.2017.08.006

文献信息

• N6-α-haloacyl sydnone imine derivatives
  作者：A. S. Samarskaya、I. A. Cherepanov、I. A. Godovikov、V. N. Kalinin

  DOI：10.1134/s0012500815080017

  日期：2015.8

  A preparative method of synthesis of N6-α-haloacyl sydnone imine derivatives has been developed. These compounds are convenient intermediates for the synthesis of a large variety of N6-α-amino-substituted and N6-α-thio-substituted acyl derivatives of sydnone imines. The obtained sydnone imine derivatives may be of interest in the context of searching for new physiologically active compounds.

  开发了一种合成 N6-α-卤代酰基 sydnone 亚胺衍生物的制备方法。这些化合物是合成大量 N6-α-氨基取代和 N6-α-硫代取代的 sydnone 亚胺酰基衍生物的方便中间体。获得的sydnone亚胺衍生物可能在寻找新的生理活性化合物的背景下感兴趣。
• Synthesis, X-ray Analysis, Biological Evaluation and Molecular Docking Study of New Thiazoline Derivatives
  作者：Yahia N. Mabkhot、H. Algarni、Abdulrhman Alsayari、Abdullatif Bin Muhsinah、Nabila A. Kheder、Zainab M. Almarhoon、Faiz A. Al-aizari

  DOI：10.3390/molecules24091654

  日期：——

  A series of new thiazoline derivatives were synthesized. Structure analyses were accomplished employing 1H-NMR, 13C-NMR, X-ray and MS techniques. The in vitro antitumor activities were assessed against human hepatocellular carcinoma (HepG-2) and colorectal carcinoma (HCT-116) cell lines. The results revealed that the thiazolines 5b and 2c exhibited significant activity against the two cell lines. The

  合成了一系列新的噻唑啉衍生物。使用1H-NMR、13C-NMR、X-射线和MS技术完成结构分析。针对人肝细胞癌 (HepG-2) 和结直肠癌 (HCT-116) 细胞系评估了体外抗肿瘤活性。结果表明，噻唑啉 5b 和 2c 对两种细胞系表现出显着的活性。体外抗菌筛选表明，噻唑啉 2c、5b 和 5d 对沙门氏菌具有良好的抑制活性。此外，噻唑啉 2e 和 5b 对大肠杆菌的抑制活性与参考化合物庆大霉素的抑制活性相当。
• A Facile Synthesis of Thiazole‐2(3<i>H</i>)‐thiones Through [Hydroxy(tosyloxy)iodo]benzene
  作者：Ranjana Aggarwal、Rashmi Pundeer、Vinod Kumar、Vishwas Chaudhri、Shiv P. Singh、Om Prakash

  DOI：10.1081/scc-200025631

  日期：2004.1.1

  Abstract A one‐pot facile synthesis of thiazole‐2(3H)‐thiones (4) has been achieved by hypervalent iodine oxidation of ketones (1) using [hydroxy(tosyloxy)iodo]benzene, followed by the treatment of the reaction mixture with dithiocarbamate salts (3). The intermediate α‐tosyloxyketones (2) have also been isolated and converted to the target compounds.

  摘要 通过使用 [羟基（甲苯磺酰氧基）碘] 苯对酮（1）进行高价碘氧化，然后用反应混合物处理，实现了噻唑-2（3H）-硫酮（4）的一锅简便合成。二硫代氨基甲酸盐 (3)。中间体 α-甲苯磺酰氧基酮 (2) 也已被分离并转化为目标化合物。
• 5-acyl-2-thiazolesulfenamides
  申请人：MONSANTO CHEMICALS

  公开号：US02841583A1

  公开（公告）日：1958-07-01

  The invention comprises compounds of the formula: <;FORM:0790800/IV (b)/1>; wherein R and R1 are hydrocarbon, chlorine-substituted hydrocarbon, alkoxy, carbonyl, carbalkoxy-substituted hydrocarbon radicals or sulphur-containing heterocyclic radicals having between them 8 to 20 carbon atoms, X-is the anion of a therapeutically acceptable non-toxic acid and Z contains not more than 7 carbon atoms and is a carbalkoxy radical, carbamyl radical, N-dialkylcarbamyl radical, benzoyl radical, acetyl radical or hydrogen. Such compounds are obtained by quaternizing a compound of the general formula: <;FORM:0790800/IV (b)/2>; with a quaternizing agent of the general formula R1X where Z1 is a nitroso radical or an organic radical containing not more than seven carbon atoms and is a carbalkoxy, benzoyl, N-dialkylcarbamyl, carbamyl or acetyl radical, compounds wherein Z is hydrogen being prepared by the additional step of hydrolysing compounds wherein Z is a carbalkoxy radical or of hydrogenating compounds prepared from those wherein Z1 is a nitroso radical. In examples: (1) N-carbethoxy-N1-nonylpiperazine is reacted with methyl iodide to give N-carbethoxy - N1 - methyl - N1 - n - nonylpiperazinium iodide; (2) N - carbethoxy - N1 - methylpiperazine and n-dodecyl bromide are reacted to give N-carbethoxy-N1-methyl-N1-n-dodecylpiperazinium bromide; (3) N-nitroso-N1-benzylN1-methyl-piperazinium chloride is hydrogenated using a Raney nickel catalyst to give N-benzyl-N-methylpiperazinium chloride hydrochloride. In a generally similar manner to (1) there are prepared (4) N-carbethoxy-N1-allyl-N1(a - carbethoxyethyl) piperazinium bromide; (5) N - methyl - N - n - tridecylpiperazinium chloride hydrochloride; (6) N - benzoyl - N1-methyl - N1 - n - dodecylpiperazinium bromide; (7) N - dimethylcarbamyl - N1 - methyl - N1-benzylpiperazinium chloride; (8) N - carbethoxy - N1 - methyl - N1 - (2 - heptynyl) - piperazinium bromide. A list is given of similarly prepared compounds, the radicals in specific compounds being selected from (at Z) carbethoxy, carbomethoxy, benzoyl, acetyl, carbamyl, dimethylcarbamyl and hydrogen; (at R) methyl, ethyl, butyl, benzyl, phenethyl and allyl; and (at R1) heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, undecenyl, propynyl, heptynyl, benzyl, p-chlorobenzyl, 2,4-dichlorobenzyl, p-methoxybenzyl, o- and m-methylbenzyl, phenylallyl, benzoylmethyl, a - or b -thenyl, carbdodecyloxymethyl and a -carbethoxyethyl radicals. N - benzoyl - N1 - methylpiperazine and N - dimethyl - carbamyl - N1 - methylpiperazine are prepared by reaction of N-methylpiperazine with the appropriate acid chlorides.

  该发明涉及公式如下的化合物：<;FORM:0790800/IV (b)/1>; 其中R和R1是烃基，氯代烃基，烷氧基，羰基，羰基烷氧基取代的烃基基团或含硫杂环基团，它们之间有8到20个碳原子，X是治疗上可接受的无毒酸的阴离子，Z含有不超过7个碳原子，是羰基烷氧基基团，氨基甲酰基基团，N-二烷基氨基甲酰基基团，苯甲酰基基团，乙酰基基团或氢。这些化合物是通过用一般式为<;FORM:0790800/IV (b)/2>;的化合物与一般式为R1X的季铵化试剂季铵化得到的，其中Z1是亚硝基基团或含不超过七个碳原子的有机基团，是羰基烷氧基基团，苯甲酰基，N-二烷基氨基甲酰基，氨基甲酰基或乙酰基基团，其中Z为氢的化合物是通过额外的水解步骤制备的，其中Z为羰基烷氧基基团或氢化由Z1为亚硝基基团制备的化合物。例如：（1）N-羧乙氧基-N1-壬基哌嗪与碘甲烷反应，得到N-羧乙氧基-N1-甲基-N1-壬基哌嗪碘化铵；（2）N-羧乙氧基-N1-甲基哌嗪和正十二溴化物反应，得到N-羧乙氧基-N1-甲基-N1-正十二基哌嗪溴化铵；（3）N-亚硝基-N1-苄基N1-甲基哌嗪盐酸盐经Raney镍催化氢化，得到N-苄基-N-甲基哌嗪盐酸盐。类似于（1）的方式制备了（4）N-羧乙氧基-N1-烯丙基-N1（a-羧乙氧基乙基）哌嗪溴化铵；（5）N-甲基-N-正十三基哌嗪盐酸盐；（6）N-苯甲酰基-N1-甲基-N1-正十二基哌嗪溴化铵；（7）N-二甲基氨基甲酰基-N1-甲基-N1-苄基哌嗪盐酸盐；（8）N-羧乙氧基-N1-甲基-N1-（2-庚炔基）-哌嗪溴化铵。列出了类似制备的化合物的列表，特定化合物中的基团从（在Z处）羧乙氧基，羰甲氧基，苯甲酰基，乙酰基，氨基甲酰基，二甲基氨基甲酰基和氢中选择；（在R处）甲基，乙基，丁基，苄基，苯乙基和烯丙基中选择；（在R1处）庚基，辛基，壬基，癸基，十一烷基，十二烷基，十三烷基，十四烷基，十五烷基，十六烷基，十一烯基，丙炔基，庚炔基，苯甲基，对氯苯甲基，2,4-二氯苯甲基，对甲氧基苯甲基，邻-和间-甲基苯甲基，苯基烯丙基，苯甲酰甲基，α-或β-烯基，羧十二氧甲基和α-羧乙氧基乙基基团中选择。通过N-苯甲酰基-N1-甲基哌嗪和N-二甲基氨基甲酰基-N1-甲基哌嗪与适当的酸氯化物反应制备N-苯甲酰基-N1-甲基哌嗪和N-二甲基氨基甲酰基-N1-甲基哌嗪。

• Morpholine Compound
  申请人：Tanaka Yoshihito

  公开号：US20070265257A1

  公开（公告）日：2007-11-15

  A compound represented by the formula (1) wherein ring A is aryl optionally having substituent(s) and the like; ring B is arylene optionally having substituent(s) and the like; m=0-2; n=1-5; X is a bond and the like; Y is a bond and the like; and Z is hydrogen atom and the like or a pharmaceutically acceptable salt thereof, and a hydrate or solvate thereof have affinity for CCR3, and can be pharmaceutical products for the treatment and/or prophylaxis of immune or inflammatory diseases.

  化合物的化学式为(1)，其中环A是芳基，可选地具有取代基等；环B是芳烃，可选地具有取代基等；m=0-2；n=1-5；X是键等；Y是键等；Z是氢原子等或其药学上可接受的盐，其水合物或溶剂化物具有对CCR3的亲和力，并可用于治疗和/或预防免疫或炎症性疾病的药物产品。