IND9413 | 224033-53-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: IND9413
• 英文别名: 6-(2-naphthyl)imidazo[2,1-b]thiazole；6-(naphthalen-2-yl)imidazo[2,1-b]thiazole；6-Naphthalen-2-ylimidazo[2,1-b][1,3]thiazole
• CAS: 224033-53-8
• 化学式: C₁₅H₁₀N₂S
• mdl: MFCD01456273
• 分子量: 250.324
• InChiKey: COTLOLWHOHUCAN-UHFFFAOYSA-N

物化性质

• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  IND9413 在 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 6.0h， 生成 (E)-6-(naphthalen-2-yl)imidazo[2,1-b]thiazole-5-carbaldehyde O-(3,4-dichlorobenzyl) oxime
  参考文献：
  名称：

  DL5050, a Selective Agonist for the Human Constitutive Androstane Receptor

  摘要：

  The constitutive androstane receptor (CAR) is a xenobiotic sensor governing the transcription of genes involved in drug disposition, energy homeostasis, and cell proliferation. However, currently available human CAR (hCAR) agonists are nonselective, which commonly activate hCAR along with other nuclear receptors, especially the closely related human pregnane X receptor (hPXR). Using a well-known hCAR agonist CITCO as a template, we report our efforts in the discovery of a potent and highly selective hCAR agonist. Two of the new compounds of the series, 18 and 19 (DL5050), demonstrated excellent potency and selectivity for hCAR over hPXR. DL5050 preferentially induced the expression of CYP2B6 (target of hCAR) over CYP3A4 (target of hPXR) on both the mRNA and protein levels. The selective hCAR agonist DL5050 represents a valuable tool molecule to further define the biological functions of hCAR, and may also be used as a new lead in the discovery of hCAR agonists for various therapeutic applications.

  DOI：

  10.1021/acsmedchemlett.9b00079
• 作为产物：
  描述：

  2-萘乙酮 在 sodium carbonate 作用下， 反应 1.5h， 生成 IND9413
  参考文献：
  名称：

  高价碘（III）磺酸盐在液体PEG-400中介导的6–Arylimidazo [2,1–b]噻唑的合成

  摘要：

  通过与芳基酮，高价碘（III）磺酸盐和2-氨基苯甲酸酯反应，将PEG-400 [聚（乙二醇-400）]用作反应生成6-芳基咪唑[2,1-b]噻唑的一锅法反应介质。氨基噻唑。已经观察到速率显着提高和产量提高。

  DOI：

  10.1002/jccs.201190103

文献信息

• Metal-Free Oxidative Deamination Cross-Coupling of Imidazo­heterocycles with 2-Aminobenzothiazoles
  作者：Ri-Yuan Tang、Xiao-Ming Ji、Li Xu、Yun Yan、Fan Chen

  DOI：10.1055/s-0035-1560395

  日期：——

  metal-free oxidative deamination–cross-coupling of imidazoheterocycles with 2-aminobenzothiazoles in the presence of tert-butyl nitrite is reported for the first time. This simple protocol tolerates a wide range of functional groups to afford various benzothiazole–imidazoheterocycles in moderate to excellent yields, with the release of nitrogen and water as benign byproducts. A metal-free oxidative deam

  摘要 首次报道了在亚硝酸叔丁酯存在下，咪唑杂环与2-氨基苯并噻唑的无金属氧化脱氨交联反应。这个简单的方案可耐受各种官能团，以中等至极好的收率提供各种苯并噻唑-咪唑杂环，并释放出氮和水作为良性副产物。 首次报道了在亚硝酸叔丁酯存在下，咪唑杂环与2-氨基苯并噻唑的无金属氧化脱氨交联反应。这个简单的方案可耐受各种官能团，以中等至极好的收率提供各种苯并噻唑-咪唑杂环，并释放出氮和水作为良性副产物。
• [EN] COMPOUNDS FOR TREATING DUCHENNE MUSCULAR DYSTROPHY<br/>[FR] COMPOSÉS POUR TRAITER LA DYSTROPHIE MUSCULAIRE DE DUCHENNE
  申请人：SUMMIT CORP PLC

  公开号：WO2009013477A1

  公开（公告）日：2009-01-29

  Compounds of general formula (I), wherein X1, X2, X3, R1, R2, R3, Y and Z are as defined herein are useful for the treatment and prevention of Duchenne muscular dystrophy, Becker muscular dystrophy and cachexia.

  通式（I）的化合物，其中X1、X2、X3、R1、R2、R3、Y和Z的定义如本文所述，对于治疗和预防杜兴氏肌肉萎缩症、贝克氏肌肉萎缩症和消瘦症是有用的。
• Organophotoredox-Catalyzed C–H Alkylation of Imidazoheterocycles with Malonates: Total Synthesis of Zolpidem
  作者：Narendra R. Chaubey、Anant R. Kapdi、Biswanath Maity

  DOI：10.1055/s-0040-1706103

  日期：2021.4

  bromomalonates under mild conditions is reported, providing excellent yields of the products at room temperature. This is the first report involving malonates as coupling partners leading to the synthesis of a range of functionalized products including total synthesis of zolpidem, a sedative­-hypnotic drug molecule.

  在过去的几年中，由于在无金属和无过氧化物的环境中催化反应的可能性，有机光催化的C–H键功能化引起了很多关注。沿这些路线继续，报道了在温和的条件下用溴代丙二酸酯对咪唑并[1,2- a ]吡啶和相关杂环进行有机光氧化还原催化的CHH功能，可在室温下提供优异的收率。这是第一份涉及丙二酸酯作为偶联伙伴的报告，导致合成了一系列功能化产品，包括镇静催眠药物分子唑吡坦的全合成。
• NOVEL ANTIPRION COMPOUNDS
  申请人：The Regents of the University of California

  公开号：US20140329863A1

  公开（公告）日：2014-11-06

  Described herein are novel compositions and methods of treatment addressing diseases such as neurodegenerative diseases, including prion diseases and Alzheimer's disease.

  本文描述了一种新的组合物和治疗方法，用于治疗神经退行性疾病，包括朊病和阿尔茨海默病。
• Sulfonyl hydrazide induced sulfenylation of imidazoheteroarenes: A ‘catalyst and solvent free’ protocol
  作者：Sourav Mal、Manoranjan Jana

  DOI：10.1080/00397911.2022.2069506

  日期：2022.4.3

  hassle free sustainable protocol for the sulfenylation of imidazoheterocycles has been developed. Sulfonyl hydrazides have been used as the generator of active thio carrier in situ in the form of “sulfono thionate” under neat condition to produce the desired sulfenylated imidazoheterocycles in good to excellent yields. The new methodology does not demand the requirement of any solvent or catalyst by simply

  摘要 已经开发了一种简单且无忧的咪唑杂环亚磺酰化可持续方案。磺酰肼已被用作原位活性硫代载体的生成剂，在纯条件下以“磺基硫酸盐”的形式以良好至优异的产率生产所需的亚磺酰化咪唑杂环化合物。新方法不需要任何溶剂或催化剂，只需调节反应物的比例即可。因此，该方法更环保且易于处理。