N-(4-(苯并[d]恶唑-2-基)苯基)乙酰胺 | 27337-45-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: N-(4-(苯并[d]恶唑-2-基)苯基)乙酰胺
• 英文名称: N-(4-(benzo[d]oxazol-2-yl)phenyl)acetamide
• 英文别名: N-(benzo[d]oxazol-2-yl)acetamide；N-(4-benzooxazol-2-yl-phenyl)-acetamide；acetic acid-(4-benzoxazol-2-yl-anilide)；Essigsaeure-(4-benzoxazol-2-yl-anilid)；2-(Acetamidophenyl)benzoxazol；N-[4-(1,3-benzoxazol-2-yl)phenyl]acetamide
• CAS: 27337-45-7
• 化学式: C₁₅H₁₂N₂O₂
• 分子量: 252.272
• InChiKey: UWXLQEOSAWVEHW-UHFFFAOYSA-N

物化性质

• 熔点：
  212 °C
• 沸点：
  449.0±28.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)
• 溶解度：
  1.3 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-(苯并[d]恶唑-2-基)苯基)乙酰胺 在 劳森试剂 、 六甲基磷酰三胺 作用下， 反应 6.0h， 以60%的产率得到2-(4-thioacetamidophenyl)benzoxazole
  参考文献：
  名称：

  Antitumor Benzothiazoles. 7. Synthesis of 2-(4-Acylaminophenyl)benzothiazoles and Investigations into the Role of Acetylation in the Antitumor Activities of the Parent Amines

  摘要：

  2-(4-Aminophenyl)benzothiazoles display potent and selective antitumor activity against inter alia breast, ovarian, colon, and renal cell lines, but their mechanism of action, though yet to be defined, may be novel. Metabolism is suspected to play a central role in the mode of action of these benzothiazoles since drug uptake and biotransformation were observed in sensitive cell lines (e.g., breast MCF-7 and MDA 468 cells) in vitro, whereas insensitive cell lines (e.g., prostate PC 3 cells) showed negligible uptake and biotransformation. N-Acyl derivatives of the arylamines have been synthesized, and in vitro studies confirm N-acetylation and oxidation as the main metabolic transformations of 2-(4-aminophenyl)benzothiazoles, with the predominant process being dictated by the nature of the 3'-substituent. The prototype amine 3 underwent mainly N-acetylation in vitro, while 3'-substituted analogues 4 and 5 were primarily oxidized. N-Acetylation of 4 to 11 exerts a drastic dyschemotherapeutic effect in vitro, but acetylation of the halogeno congeners 5-7 gave acetylamines 12-14 which substantially retain selective antitumor activity. In vivo pharmacokinetic studies in rats confirmed rapid and exclusive N-acetylation of the 3'-methyl analogue 4, but less acetylation with the 3'-chloro analogue 5. Distinct expression patterns of N-acetyltransferase NAT1 and NAT2 have been demonstrated in our panel of cell lines.

  DOI：

  10.1021/jm981076x
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 lead(IV) acetate 、 苯 作用下， 生成 N-(4-(苯并[d]恶唑-2-基)苯基)乙酰胺
  参考文献：
  名称：

  626.从席夫氏碱制备苯并咪唑和苯并恶唑。第一部分

  摘要：

  DOI：

  10.1039/jr9490002971

文献信息

• Palladium-catalyzed desulfitative C-arylation of a benzo[d]oxazole C–H bond with arene sulfonyl chlorides
  作者：Manli Zhang、Shouhui Zhang、Miaochang Liu、Jiang Cheng

  DOI：10.1039/c1cc14718h

  日期：——

  A palladium-catalyzed direct desulfitative C-arylation of a benzo[d]oxazole C-H bond with arene sulfonyl chlorides is described. The procedure tolerates halo, cyano, nitro, trifluoromethyl, acetyl and acetylamino groups on the phenyl ring of sulfonyl chlorides, providing the arylation products in moderate to good yields. It represents a practical and attractive alternative for the synthesis of 2-aryl

  描述了苯并[d]恶唑CH键与芳烃磺酰氯的钯催化的直接脱硫C-芳基化。该方法容许磺酰氯苯环上的卤素，氰基，硝基，三氟甲基，乙酰基和乙酰氨基基团，以中等至良好的产率提供芳基化产物。它代表了合成2-芳基苯并恶唑的实用且有吸引力的替代方法。
• Pd/Cu-Catalyzed C–H/C–H Cross Coupling of (Hetero)Arenes with Azoles through Arylsulfonium Intermediates
  作者：Ze-Yu Tian、Zeng-Hui Lin、Cheng-Pan Zhang

  DOI：10.1021/acs.orglett.1c01322

  日期：2021.6.4

  A highly efficient method for the selective formal C–H/C–H cross-coupling of azoles and (hetero)arenes was established through arylsulfonium intermediates under transition-metal catalysis, which produced a variety of 2-(hetero)aryl azoles in good to excellent yields. Advantages of the reaction included mildness, a good functional group tolerance, a wide range of substrates, a high regio- and chemoselectivity

  在过渡金属催化下，通过芳基锍中间体建立了一种用于唑类和（杂）芳烃的选择性形式 C-H/C-H 交叉偶联的高效方法，该方法可以很好地生产各种 2-（杂）芳基唑类化合物。以优异的产量。该反应的优点包括温和、官能团耐受性好、底物范围广、区域选择性和化学选择性高、一锅法以及不使用氧化剂的复杂分子的后期功能化，提供了一种有前景的策略用于过渡金属催化的唑类的 C-H 芳基化。
• Base-Free Selective <i>O</i> -Arylation and Sequential [3,3]-Rearrangement of Amidoximes with Diaryliodonium Salts: Synthesis of 2-Substituted Benzoxazoles
  作者：Wei-Min Shi、Xiao-Hua Li、Cui Liang、Dong-Liang Mo

  DOI：10.1002/adsc.201700906

  日期：2017.12.11

  of functionalized 2‐substituted benzoxazoles can be prepared in good yields from amidoximes and diaryliodonium salts by selective O‐arylation and sequential [3,3]‐rearrangement under metal‐free conditions. O‐arylation of amidoximes was promoted by 3 Å molecule sieves in the absence of a base and a sequential TFA‐mediated [3,3]‐rearrangement was used to synthesize 2‐substituted benzoxazoles. Both of

  在无金属条件下，可以通过选择性O芳基化和顺序[3,3]重排，从ox胺肟和二芳基碘鎓盐中以高收率制备各种功能化的2-取代苯并恶唑。ø偕胺肟的-arylation用3埃分子筛在不存在碱的和促进连续TFA介导的，使用[3,3] -rearrangement以合成2-取代的苯并恶唑。两者的ø -芳基产品和重排产物用宽范围敏感的官能团，如酯，醛，硝基，乙烯基，胺和酰胺基团除了卤化物的兼容。分两步以克规模制备了带有双苯并恶唑的双齿N-配体。
• Fluorescence and Structure of Proteins as measured by Incorporation of Fluorophore. II. Synthesis of Maleimide Derivatives as Fluorescence-Labeled Protein-Sulfhydryl Reagents.
  作者：Yuichi Kanaoka、Minoru Machida、Yoshio Ban、Takamitsu Sekine

  DOI：10.1248/cpb.15.1738

  日期：——

  A novel approach to studies of structure and function of proteins utilizing fluorescencelabeled specific reagent is proposed. N-[p-(2-Benzoxazolyl) phenyl] maleimide (IIIa) and N-[p-(2-benzthiazolyl) phenyl] maleimide (IIIb) were synthesized as sulfhydryl reagents of this type and the addition reaction with cysteine ester was investigated. Cyclization of maleamic acids with PPA is demonstrated to be a good method for synthesis of N-substituted maleimides.

  提出了一种利用荧光标记特定试剂研究蛋白质结构和功能的新方法。合成了N-[p-(2-苯并恶唑基)苯基]马来酰亚胺（IIIa）和N-[p-(2-苯并噻唑基)苯基]马来酰亚胺（IIIb）作为此类巯基试剂，并对其与半胱氨酸酯的加成反应进行了研究。此外，使用PPA进行马来酰胺酸的环化证明是一种合成N-取代马来酰亚胺的良好方法。
• 2-arylbenzazole compounds
  申请人：Cancer Research Campaign Technology Limited

  公开号：US06034246A1

  公开（公告）日：2000-03-07

  There are disclosed herein 2-phenylbenzazole compounds having a 3'-substituent and a 4'-NR.sup.2 R.sup.6 substituent in the phenyl group where R.sup.5 and R.sup.6 are each hydrogen or alkyl, or where the $'-NR.sup.5 R.sup.6 substituent is N-acyl (or N-benzoyl). There are also disclosed 2-phenylbenzazole compounds in the form of 4'-N sulphamate salts. Such compounds exhibit significant selective cytotoxic activity in respect of tumor cells and provide potentially useful chemotherapeutic agents for selective treatment of a range of cancers.

  本文披露了一种具有3'-取代基和4'-NR.sup.2 R.sup.6 取代基的2-苯基苯并咪唑化合物，其中R.sup.5和R.sup.6分别为氢或烷基，或者$'-NR.sup.5 R.sup.6 取代基为N-酰基（或N-苯甲酰基）。还披露了以4'-N磺酰酸盐形式存在的2-苯基苯并咪唑化合物。这些化合物在肿瘤细胞方面表现出显著的选择性细胞毒性活性，并提供了潜在有用的化疗药物，用于选择性治疗一系列癌症。