5-甲基-3-异噁唑基异硫氰酸 | 321309-33-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-甲基-3-异噁唑基异硫氰酸
• 英文名称: 5-methylisoxazolyl-3-isothiocyanate
• 英文别名: 3-isothiocyanato-5-methylisoxazole；3-Isothiocyanato-5-methyl-1,2-oxazole
• CAS: 321309-33-5
• 化学式: C₅H₄N₂OS
• mdl: MFCD02681896
• 分子量: 140.166
• InChiKey: YADFBVUOBWXDRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  70.5
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R20/21/22,R36/37/38
• 海关编码：
  2934999090
• 危险品运输编号：
  UN 2811

反应信息

• 作为反应物：
  描述：

  5-甲基-3-异噁唑基异硫氰酸 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 0.5h， 生成 1-[5-(3-methylphenylamino)-1,2,4-thiadiazol-3-yl]-propan-2-ol
  参考文献：
  名称：

  Novel 1,2,4-Thiadiazole Derivatives as Potent Neuroprotectors: Approach to Creation of Bioavailable Drugs

  摘要：

  Novel 1,2,4-thiadiazole derivatives as potent neuroprotectors were synthesized and identified. Their ability to inhibit the glutamate stimulated Ca uptake was measured. Permeation experiments on the phospholipid membranes were conducted, and the apparent permeability coefficients were obtained. The partition coefficients in n-octanol/buffer (pH 7.4) and n-hexane/buffer (pH 7.4) immiscible phases (as model systems for characterizing gastrointestinal tract membranes and BBB) were determined. A classification of the studied compounds from the standpoint of "permeability-activity" properties was proposed.

  DOI：

  10.1021/mp300011r
• 作为产物：
  描述：

  7-methyl-3-(5-methylisoxazol-3-yl)-2H-isoxazolo[2,3-a][1,3,5]triazine-2,4(3H)-dithione 以 氘代氯仿 为溶剂， 生成 5-甲基-3-异噁唑基异硫氰酸
  参考文献：
  名称：

  5-甲基-3-异恶唑基异硫氰酸酯的二聚体

  摘要：

  DOI：

  10.1007/s10593-007-0230-7

文献信息

• 4-Chlorocolchicine derivatives bearing a thiourea side chain at the C-7 position as potent anticancer agents
  作者：Hiroyuki Nishiyama、Masahiro Ono、Takuya Sugimoto、Toshio Sasai、Naoyuki Asakawa、Satoshi Ueno、Yoshitaka Tominaga、Takashi Yaegashi、Masato Nagaoka、Takeshi Matsuzaki、Noriyuki Kogure、Mariko Kitajima、Hiromitsu Takayama

  DOI：10.1039/c3md00287j

  日期：——

  A series of 4-substituted colchicine derivatives were synthesized and evaluated with an eye toward developing new anticancer agents. As a result, 4-chlorocolchicine derivatives bearing a thioureide side chain at the C-7 position were found to exhibit significant cytotoxicities to three human cancer cell lines (A549, HT-29, and HCT116). In particular, compound 26 having an ethylthioureide group at the C-7 had high antitumor activity in vivo and a broad effective dosage range. Furthermore, compound 58, which has a (5-methylpyrazol-3-yl)thioureide group at the C-7 side chain, exhibited strong cytotoxicity and desirable metabolic stability in vitro.

  合成了一系列4-取代的秋水仙碱衍生物，并对其进行了评估，旨在开发新型抗癌药物。结果发现，在C-7位带有硫脲侧链的4-氯秋水仙碱衍生物对三种人癌细胞系（A549、HT-29和HCT116）显示出显著的细胞毒性。特别是，在C-7位带有乙基硫脲的化合物26在体内具有高抗肿瘤活性，并且有效剂量范围广泛。此外，在C-7位侧链带有(5-甲基吡唑-3-基)硫脲的化合物58，在体外表现出强烈的细胞毒性和良好的代谢稳定性。
• Novel 5-N,N-disubstituted-5-amino-3-(2-oxopropyl)-1,2,4-thiadiazoles: synthesis and study of neuroprotective and antiproliferative properties
  作者：A. N. Proshin、T. P. Trofimova、O. N. Zefirova、L. N. Petrova、D. A. Skvortsov、S. O. Bachurin

  DOI：10.1007/s11172-019-2700-3

  日期：2019.12

  A series of eight novel 5-N,N-disubstituted-5-amino-3-(2-oxopropyl)-1,2,4-thiadiazoles with diverse lipophilic groups was obtained by reaction of 3-isothiocyanato-5-methylisoxazole with secondary amines. All the compounds of the series (independently on the type of the substituents) were found to be ineffective as inhibitors of calcium ions uptake in synaptosomes of rat cerebral cortex. Screening of the cytotoxicity to four cell lines (breast adenocarcinoma MCF-7, conditionnally normal breast epithelial cells MCF-10A, lung carcinoma A549, non-cancer lung fibroblasts VA13) revealed three compounds with good selectivity to cancer cells MCF-7 in comparison with non-cancer cell line MCF- 10A. These 1,2,4-thiadiazoles can serve as new leads for further study of their antitumor properties.

  获得了一系列八种新型的5-N,N-二取代-5-氨基-3-(2-氧丙基)-1,2,4-噻二唑，它们具有多样的亲脂性基团，通过3-异硫氰酸盐-5-甲基异噁唑与次级胺反应合成。该系列的所有化合物（不论取代基类型）在大鼠大脑皮层突触体中被发现对钙离子摄取无抑制效果。对四种细胞系（乳腺腺癌 MCF-7、条件正常乳腺上皮细胞 MCF-10A、肺癌 A549、非癌肺成纤维细胞 VA13）进行的细胞毒性筛选显示，与非癌细胞系 MCF-10A 相比，有三种化合物对癌细胞 MCF-7 具有良好的选择性。这些1,2,4-噻二唑可以作为进一步研究其抗肿瘤性质的新靶点。
• Screening of a series of 3,5-disubstituted 1,2,4-thiadiazoles for selectivity of cytotoxic action to cancer cells
  作者：A. N. Proshin、T. P. Trofimova、O. N. Zefirova、I. V. Zhirkina、D. A. Skvortsov、S. O. Bachurin

  DOI：10.1007/s11172-021-3116-4

  日期：2021.3

  New 3,5-disubstituted-1,2,4-thiadiazoles were synthesized and together with a series of their analogs obtained earlier were tested for cytotoxic activity to breast adenocarcinoma MCF-7 and lung carcinoma A 549 cells. The selectivity of cytotoxic action was determined in comparison to etiologically noncancerous breast epithelial cells MCF-10A and lung fibroblasts VA13. From five- to six-fold selectivity of cytotoxic action was revealed for 3,4-dichlorophenyl-3-[2-(2-morpholin-4-ylethylamino)propyl]-[1,2,4]thiadiazol-5-yl}amine and (2-5-[(4-diethylami-nobenzyl)pyridin-3-ylmethylamino]-[1,2,4]thiadiazol-3-yl}-1-methylvinyl)-(2,2,6,6-tetra-methylpiperidin-4-yl)amine in the pairs A 549/VA13 and MCF-7/MCF-10A, respectively. Some structure—property relationships for the compounds under study were discussed.

  合成了新的 3,5-二取代-1,2,4-噻二唑，并与之前获得的一系列类似物一起测试了对乳腺癌 MCF-7 和肺癌 A 549 细胞的细胞毒活性。与病因学上的非癌性乳腺上皮细胞 MCF-10A 和肺成纤维细胞 VA13 相比，确定了细胞毒作用的选择性。 3,4-二氯苯基-3-[2-(2-吗啉-4-基乙基氨基)丙基]-[1,2,4]噻二唑-5-基的细胞毒性作用选择性提高了五到六倍}胺和(2-5-[(4-二乙基氨基苄基)吡啶-3-基甲基氨基]-[1,2,4]噻二唑-3-基}-1-甲基乙烯基)-(2,2,6, 6-四甲基哌啶-4-基)胺分别为 A 549/VA13 和 MCF-7/MCF-10A 对。讨论了所研究化合物的一些结构-性质关系。
• Towards the rational design of novel drugs based on solubility, partitioning/distribution, biomimetic permeability and biological activity exemplified by 1,2,4-thiadiazole derivatives
  作者：T. V. Volkova、I. V. Terekhova、O. I. Silyukov、A. N. Proshin、A. Bauer-Brandl、G. L. Perlovich

  DOI：10.1039/c6md00545d

  日期：——

  Novel 1,2,4-thiadiazole derivatives as potent neuroprotectors were synthesized and their solubility, distribution coefficients, permeability and biological properties were studied.

  合成了新型1,2,4-噻二唑衍生物，作为有效的神经保护剂，并研究了它们的溶解度、分配系数、渗透性和生物学性质。
• General Access to <i>N</i> −CF ₃ Secondary Amines and Their Transformation to <i>N</i> −CF ₃ Sulfonamides
  作者：Leibing Wang、Jieping Wang、Sitao Ye、Beihan Jiang、Zihao Guo、Yasir Mumtaz、Wenbin Yi

  DOI：10.1002/anie.202212115

  日期：2022.12.5

  A new and mild method for the generation of HF from triethylsilane and silver fluoride leads to a highly efficient one-pot synthesis of N−CF3 secondary amines. Novel N−CF3 sulfonamides were constructed from these promising amine building blocks and sulfonyl bromides in an unprecedented route.

  一种由三乙基硅烷和氟化银生成 HF 的新型温和方法可实现N -CF 3仲胺的高效一锅法合成。新型N -CF 3磺胺类化合物是通过前所未有的途径由这些有前途的胺结构单元和磺酰溴构建而成的。