phenyl 2-thioxobenzo[d]oxazole-3(2H)-carboxylate | 49740-35-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: phenyl 2-thioxobenzo[d]oxazole-3(2H)-carboxylate
• 英文别名: phenyl 2-thioxo-3H-benzoxazole-3-carboxylate；3-(phenoxycarbonyl)benzoxazole-2(3H)-thione；N-(phenoxycarbonyl)benzoxazoline-2-thione；N-Phenoxycarbonylbenzoxazole-2-thione；2-thioxo-benzooxazole-3-carboxylic acid phenyl ester；phenyl 2-thioxo-1,3-benzoxazole-3(2H)-carboxylate；phenyl 2-sulfanylidene-1,3-benzoxazole-3-carboxylate
• CAS: 49740-35-4
• 化学式: C₁₄H₉NO₃S
• 分子量: 271.296
• InChiKey: RPRRUBBAUIEOQB-UHFFFAOYSA-N

物化性质

• 沸点：
  392.9±25.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  phenyl 2-thioxobenzo[d]oxazole-3(2H)-carboxylate 以 甲苯 、 苯 为溶剂， 生成 phenyl 2-[(3,3,4,4-tetramethylthietan-2-ylidene)amino]phenyl carbonate
  参考文献：
  名称：

  Photocycloaddition Reactions of Alkyl and Aryl 2-Thioxo-3H-benzoxazole- 3-carboxylates to Alkenes

  摘要：

  The photochemical reactions of alkyl and aryl 2-thioxo-3H-benzoxazole-3-carboxylates 1 have been examined. Irradiation of 1 in the presence of tetra- and trisubstituted alkenes 2a and 2b, 2-methylprop-2-ene nitrile 2e, and dienes 2f and 2g gave [2+2] cycloadducts of the C=S bond of 2-thioxobenzoxazoles and the C=C bond of alkenes, spiro[benzoxazole-thietanes] 3, 4, 8-13, 15, 18, 20, 23-26 in moderate-to-good yields. The photoaddition reactions proceed in a regiospecific manner. The spirocyclic compounds obtained are indefinitely stable at room temperature. Irradiation of la in the presence of 1,1- and 1,2-disubstituted alkenes 2c and 2d yielded the products 5-7 of oxazole-ring cleavage. Compound 1d also underwent photoaddition with alkenes to yield spiro[benzoxazole-thietanes] and/or 2-substituted benzoxazoles and/or iminothietanes, depending on the nature of the substituents present in the alkenes. On intramolecular [2 + 2] photoadduct, tetracyclic 27, was obtained, when ethenyl 2-thioxobenzoxazole-3-carboxylate 1e was irradiated.

  DOI：

  10.1002/1522-2675(200208)85:8<2383::aid-hlca2383>3.0.co;2-e
• 作为产物：
  描述：

  氯甲酸苯酯 、 2-巯基苯并恶唑 反应 1.0h， 生成 phenyl 2-thioxobenzo[d]oxazole-3(2H)-carboxylate
  参考文献：
  名称：

  [EN] INHIBITORS TO TARGET HIV-1 NEF-CD80/CD86 INTERACTIONS FOR THERAPEUTIC INTERVENTION
  [FR] INHIBITEURS DESTINÉS À CIBLER DES INTERACTIONS NEF-CD80/CD86 DU VIH-1 POUR UNE INTERVENTION THÉRAPEUTIQUE

  摘要：

  公式I、II和III的化合物及其立体异构体、药学上可接受的盐、多型体、溶剂合物和水合物在本公开中有所描述。所述化合物可在需要的受试者中恢复免疫激活，以应对感染或与HIV感染相关的疾病。

  公开号：

  WO2020035880A1

文献信息

• Photocycloaddition of N-alkoxycarbonylbenzoxazole-2-thiones to alkenes: isolation of stable aminothietanes
  作者：Takehiko Nishio

  DOI：10.1039/a900699k

  日期：——

  N-Alkoxy- and N-aryloxycarbonylbenzoxazole-2-thiones 1 undergo photocycloaddition with alkenes 2 in a regiospecific manner to yield stable spirocyclic aminothietanes 3–4, 7–9 and 11 in fair to high yields.

  N-烷氧基和N-芳氧基酰基苯并恶唑-2-硫酮1在光引发下与烯烃2发生区域选择性的光环加成反应，以中等至高产率生成稳定的螺环氨基噻吩3-4、7-9和11。
• Photoaddition Reactions of Benzoxazole-2(3H)-thiones to Cycloalkenes and Heteroaromatics
  作者：Takehiko Nishio、Kiyoko Shiwa、Masami Sakamoto

  DOI：10.1002/hlca.200390266

  日期：2003.10

  cyclohexa-1,4-diene (2d), and indene (2e) yielded 2-substituted benzoxazoles 4–13, 18 and 19, and iminothietanes 14–17, by intramolecular trapping of the acyl or MeOCO and PhOCO groups by thiolate anion of the zwitterionic intermediate I and by the phenolate anion of the zwitterionic intermediate II, respectively, derived from the spirocyclic amino-thietanes AT formed by [2+2] cycloaddition of the CS bond of

  苯并恶唑-2-硫酮的光加成反应1与环烯烃2和杂芳族化合物3进行了检查。的照射Ñ -acylbenzoxazole -2-硫酮1A和1B，和3-（甲氧羰基） -苯并恶唑-2-和3-（苯氧基羰基）（3 ħ）-thiones（1F和1H。，RESP）在环烯烃的存在2A -图2c，环己-1,4-二烯（2D）和茚（2E），得到2-取代的苯并恶唑4 - 13，18和19，和iminothietanes 14- 17，由两性离子中间体的硫醇盐阴离子的酰基或MeOCO和PhOCO基团的分子内俘获我和由两性离子中间体的酚盐阴离子II，分别从螺环氨基thietanes衍生AT通过形成[2 + 2] 1的CS键和2的CC键的环加成。在杂芳族化合物3的存在下照射1只能得到2-取代的苯并恶唑20 – 33。
• [EN] DIPHOSPHATE MIMETICS AND USES THEREOF<br/>[FR] MIMÉTIQUES DE DIPHOSPHATE ET LEURS UTILISATIONS
  申请人：HARVARD COLLEGE

  公开号：WO2013006758A1

  公开（公告）日：2013-01-10

  The present invention provides compounds of Formulae (I)-(V), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. In one aspect, compounds of the present invention are useful as glycosyltransferase inhibitors, in particular, O-linked N- acetylglucosamine (O-GlcNAc) transferase (OGT) inhibitors. In another aspect, compounds of the present invention are useful as kinase inhibitors, in particular, PLKl inhibitors, GSK3P inhibitors, or MAPKAPK2 inhibitors. The present invention further provides methods of using the inventive compounds, e.g., as biological probes to study the inhibition of OGT and/or kinase activity and as therapeutics, e.g., for the treatment of OGT-associated and/or kinase-associated conditions.

  本发明提供了式（I）-（V）的化合物，其药学上可接受的盐以及药物组合物。在一个方面，本发明的化合物可用作糖基转移酶抑制剂，特别是O-连接N-乙酰葡萄糖胺（O-GlcNAc）转移酶（OGT）抑制剂。在另一个方面，本发明的化合物可用作激酶抑制剂，特别是PLKl抑制剂、GSK3P抑制剂或MAPKAPK2抑制剂。本发明还提供了使用创新化合物的方法，例如作为生物探针来研究OGT和/或激酶活性的抑制，以及作为治疗剂，例如用于治疗与OGT相关和/或激酶相关的疾病。
• Acylation and Alkoxycarbony-lation of Benzoxazoline-2-thione and Benzothiazoline-2-thione
  作者：Takehiko Nishio、Kiyoko Shiwa

  DOI：10.3987/com-03-s(p)10

  日期：——

  Acylation of benzoxazoline-2-thione (1) and benzothiazoline-2-thione (2) with acetic anhydride (3) and acyl chlorides (4) gave N-acyl (5, 6) and/or S-acyl (7, 8) derivatives depending on the nature of acylating agents and bases used. Alkoxycarbonylation of 1 with aralkyl chlorocarbonates (9) gave N-alkoxycarbonyl derivatives (10) mainly, while that of 2 with aralkyl chloroccarbonates (9) gave S-alkoxycarbonyl derivatives (12) exclusively. Photolysis of N-acyl derivatives (5 or 6) in the presence of alcohols afforded 1 or 2, respectively, together with esters (16).
• DIPHOSPHATE MIMETICS AND USES THEREOF
  申请人：Kahne Suzanne Walker

  公开号：US20140163079A1

  公开（公告）日：2014-06-12

  The present invention provides compounds of Formulae (I)-(V), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. In one aspect, compounds of the present invention are useful as glycosyltransferase inhibitors, in particular, O-linked N-acetylglucosamine (O-GlcNAc) transferase (OGT) inhibitors. In another aspect, compounds of the present invention are useful as kinase inhibitors, in particular, PLK1 inhibitors, GSK3P inhibitors, or MAPKAPK2 inhibitors. The present invention further provides methods of using the inventive compounds, e.g., as biological probes to study the inhibition of OGT and/or kinase activity and as therapeutics, e.g., for the treatment of OGT-associated and/or kinase-associated conditions.