(3Z)-1H-indole-2,3-dione 3-[(4-chlorophenyl)hydrazone] | 100460-67-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3Z)-1H-indole-2,3-dione 3-[(4-chlorophenyl)hydrazone]
• 英文别名: 3-(4-chloro-phenylhydrazono)-2-indolone
• CAS: 100460-67-1
• 化学式: C₁₄H₁₀ClN₃O
• 分子量: 271.706
• InChiKey: AYGQGXKXYLVIMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.49
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3Z)-1H-indole-2,3-dione 3-[(4-chlorophenyl)hydrazone] 在 劳森试剂 、 N-氯代丁二酰亚胺 作用下， 以 乙酸乙酯 、 xylene 为溶剂， 反应 2.0h， 生成 2-(4-chlorophenyl)-2H-[1,2,3]thiadiazolo[5,4-b]indole hydrochloride
  参考文献：
  名称：

  A new synthetic method for the 2H-[1,2,3]thiadiazolo[5,4-b]indoles

  摘要：

  The systematic study of oxidative cyclization of 3-hydrazono-1,3 -dihydroindole-2-thiones has been carried out and a series of new 2H-[1,2,3]thiadiazolo[5,4-b]indoles has been prepared. The elaborated reaction represents an efficient method for the synthesis of fused 1,2,3-thiadiazoles. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.059
• 作为产物：
  描述：

  对氯苯肼盐酸盐 、 靛红 以 甲醇 为溶剂， 以96%的产率得到(3Z)-1H-indole-2,3-dione 3-[(4-chlorophenyl)hydrazone]
  参考文献：
  名称：

  Synthesis and biophysical evaluation of arylhydrazono-1H-2-indolinones as β-amyloid aggregation inhibitors

  摘要：

  A series of isatin-3-arylhydrazones were synthesized and evaluated in vitro as inhibitors of A beta(1-40) aggregation using a thioflavin T fluorescence method. An exploration of the effects on A beta(1-40) aggregation of a number of diverse substituents at phenylhydrazone group and 5,6- positions of the indolinone nucleus led us to single out some new anti-aggregating compounds with IC50 values in the low micromolar range. The most active compounds carry methoxy- or hydroxy- substituents in the indolinone 5,6-positions and lipophilic groups such as iPr and Cl at 4'- and 3'-position, respectively, of the phenylhydrazone moiety. Two derivatives are noteworthy, namely 18 (IC50 = 0.4 mu M) and 42 (IC50 = 1.1 mu M). The in vitro effects of the highly active, water soluble, compound 42 on the temporal evolution of A beta(1-40) fibrils formation were further investigated by circular dichroism spectroscopy, transmission electron microscopy and dynamic light scattering studies, which clearly showed that this compound delayed and lowered the amyloid fibril formation. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.015

文献信息

• Synthesis and evaluation of oxindoles as promising inhibitors of the immunosuppressive enzyme indoleamine 2,3-dioxygenase 1
  作者：Saurav Paul、Ashalata Roy、Suman Jyoti Deka、Subhankar Panda、Gopal Narayan Srivastava、Vishal Trivedi、Debasis Manna

  DOI：10.1039/c7md00226b

  日期：——

  oxindoles from L-Trp, tryptamine and isatin. Compounds with C3-substituted oxindole moieties showed moderate inhibitory activity against the purified human IDO1 enzyme. Their optimization led to the identification of potent compounds, 6, 22, 23 and 25 (IC50 = 0.19 to 0.62 μM), which are competitive inhibitors of IDO1 with respect to L-Trp. These potent compounds also showed IDO1 inhibition potencies in

  吲哚胺2,3-二加氧酶1（IDO1）被认为是治疗癌症，慢性感染和其他与免疫抑制有关的疾病的重要治疗靶标。在理解IDO1酶的催化机理方面的最新进展表明，L-色氨酸（L- Trp ）向N-甲酰基kynurenine的转化通过环氧化物中间态进行。因此，我们从L -Trp，色胺和靛红合成了一系列3-取代的羟吲哚。具有C3取代的羟吲哚基团的化合物对纯化的人IDO1酶表现出中等的抑制活性。他们的优化导致了鉴定有效的化合物的，6，22，23和25（IC 50 = 0.19至0.62μM），它们是IDO1相对于L -Trp的竞争性抑制剂。这些有效的化合物还在MDA-MB-231细胞中的低微摩尔范围（IC 50 = 0.33–0.49μM）中显示出IDO1抑制能力。这些有效化合物在不同模型的癌细胞（MDA-MB-231，A549和HeLa）和巨噬细胞（J774A.1）中的细胞毒性微不足道。对于这些化合物，还
• Indium(<scp>iii</scp>)-catalyzed efficient synthesis of 3-arylhydrazonoindolin-2-ones and their fluorescent metal sensing studies
  作者：Shreedhar Devkota、Sonaimuthu Mohandoss、Yong Rok Lee

  DOI：10.1039/d1nj05715d

  日期：——

  In(iii)-catalyzed strategy for the preparation of 3-arylhydrazonoindolin-2-ones from 3-diazoindoles is developed and used for Fe³⁺ and Hg²⁺ ion sensing.

  研发了一种以In(iii)为催化剂的策略，用于从3-重氮吲哚制备3-芳基肼基吲哚啉-2-酮，并用于Fe3+和Hg2+离子传感。
• Visible-light-absorbing C–N cross-coupling for the synthesis of hydrazones involving C(sp²)–H/C(sp³)–H functionalization
  作者：Ambuj Kumar Kushwaha、Suresh Kumar Maury、Arsala Kamal、Himanshu Kumar Singh、Shikha Pandey、Sundaram Singh

  DOI：10.1039/d2cc07001d

  日期：——

  An efficient C–N cross-coupling approach for the synthesis of hydrazones was developed through C(sp2)–H and C(sp3)–H functionalization of indole and methylarene under visible light irradiation using photocatalyst eosin Y, ethanol:water as a green solvent and atmospheric air as an oxidant. With the aid of eosin Y, the C–H bonds of indole and methylarenes were activated followed by coupling with arylhydrazines

  通过 C(sp 2 )–H 和 C(sp 3)–H 功能化吲哚和甲基芳烃在可见光照射下使用光催化剂曙红 Y，乙醇：水作为绿色溶剂和大气空气作为氧化剂。在曙红 Y 的帮助下，吲哚和甲基芳烃的 C-H 键被激活，然后与芳基肼偶联。该程序适用于具有良好官能团相容性的各种底物，提供了一种创造性的方法，可以用廉价且易于获得的原材料制造腙。没有金属、低成本、环境友好、绿色溶剂、无毒、易于处理以及利用可见光等可再生能源是该方法的一些主要优势。
• US3966900A
  申请人：——

  公开号：US3966900A

  公开（公告）日：1976-06-29
• US4058607A
  申请人：——

  公开号：US4058607A

  公开（公告）日：1977-11-15