2-chloro-1-(5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)ethenone | 380196-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-chloro-1-(5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)ethenone
• 英文别名: 2-chloro-1-[5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]ethan-1-one；2-chloro-1-[3-(4-methoxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]ethanone
• CAS: 380196-84-9
• 化学式: C₁₈H₁₇ClN₂O₂
• mdl: MFCD02720609
• 分子量: 328.798
• InChiKey: YJDRECSFQDETIE-UHFFFAOYSA-N

物化性质

• 熔点：
  129 °C(Solv: ethanol (64-17-5))
• 沸点：
  473.1±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-1-(5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)ethenone 在 sodium azide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 2-azido-1-[5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone
  参考文献：
  名称：

  高效吡唑啉基三唑的设计，合成和抗菌研究

  摘要：

  摘要 （pyrazolinyltriazole杂交的文库 3A - 升 ， 4A - 升 ）中的溶液通过无溶剂条件下，叠氮基乙酰吡唑啉和乙炔二酯的叠氮化物-炔烃的偶极（胡伊斯根）环加成来合成。研究了杂种对四种人类病原体的体外抗菌活性。 与标准药环丙沙星相比， 大肠杆菌 （ATCC 25922）， 肺炎克雷伯菌 （ATCC 13883）， 奇异变形杆菌 （ATCC 12453）和 金黄色葡萄球菌 （ATCC 29213）。合成的24种化合物中有6种[ 3d ， 最小抑菌浓度（MIC）为3.9 µg / mL]的 k ， l 和 4d ， k ， l 比环丙沙星更有效。实际上，所有24种新化合物对 金黄色葡萄球菌 的高抗菌活性 表明，具有这种吡唑啉基三唑骨架的此类化合物可能会作为一类新的潜在抗菌剂出现。此外，其他三种病原体也被大多数合成化合物（ 3a ， c ， d ， g ， k ， l ，

  DOI：

  10.1007/s11164-016-2774-6
• 作为产物：
  描述：

  4-甲氧基查耳酮 在 一水合肼 、 三乙胺 作用下， 以 乙醇 、 苯 为溶剂， 反应 5.0h， 生成 2-chloro-1-(5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)ethenone
  参考文献：
  名称：

  Synthesis and Antimicrobial Activities of Some 1-[(N, N-Disubstitutedthiocarbamoylthio)acetyl]-3,5-diaryl-2-pyrazolines

  摘要：

  The increasing clinical importance of drug-resistant fungal and bacterial pathogens has lent additional urgency to microbiological research and new antimicrobial compound development. For this put-pose, new pyrazoline derivatives were synthesized and evaluated for antimicrobial activity.Some 1-[(N,N-disubstitutedthiocarbamoylthio)acetyl]-3,5-dialyl-2-pyrazolines derivatives were synthesized by reacting 1-(chloroacetyl)-3,5-diaryl-2-pyrazolines with appropriate potassium salts of secondary amine dithiocarbamic acids. The chemical structures of the compounds were elucidated by IR, H-1-NMR, and FAB(+)-MS spectral data. Their antimicrobial activities against Staphylococcus aureus (B-767), Escherichia coli (B-3704), Pseudomonas aeruginosa (ATCC 27853), Proteus vulgaris (NRLL B-123), and Candida. albicans (NRRL-27077) were investigated. The results showed that some of the compounds have notable activity against S. aureus and C. albicans.

  DOI：

  10.1080/104265090930452

文献信息

• Pharmacophore hybridization approach to discover novel pyrazoline-based hydantoin analogs with anti-tumor efficacy
  作者：Neha Upadhyay、Kalpana Tilekar、Fulvio Loiodice、Natalia Yu. Anisimova、Tatiana S. Spirina、Darina V. Sokolova、Galina B. Smirnova、Jun-yong Choe、Franz-Josef Meyer-Almes、Vadim S. Pokrovsky、Antonio Lavecchia、CS Ramaa

  DOI：10.1016/j.bioorg.2020.104527

  日期：2021.2

  antitumor hybrid incorporating diaryl pyrazoline and pyrrolidine-2,5-dione scaffolds with “imidazoline-2,4-dione” moiety has been incorporated. Complete biological studies revealed the most potent analog among all i.e. compound H13, which was at-least 10-fold more potent compared to the corresponding pyrrolidine-2,5-dione, in colon and breast cancer cells. In-vitro studies showed activation of caspases

  为了寻找新的、更安全的抗癌药物，采用了两种特殊支架（即二芳基吡唑啉和咪唑烷-2,4-二酮（乙内酰脲））的结构引导药效团杂交策略，产生了一系列新型化合物（H1-H22 ））。在此，我们最近报道的抗肿瘤杂合体的“吡咯烷-2,5-二酮”部分的生物等排替换，该杂合体结合了二芳基吡唑啉和吡咯烷-2,5-二酮支架，并具有“咪唑啉-2,4-二酮”部分。 。完整的生物学研究揭示了所有类似物中最有效的类似物，即化合物H13，其在结肠癌细胞和乳腺癌细胞中的效力比相应的吡咯烷-2,5-二酮至少高10倍。体外研究表明，半胱天冬酶被激活，细胞周期 G0/G1 期停滞，抗凋亡蛋白 (Bcl-2) 表达减少，DNA 损伤增加。对 HT-29（人结直肠腺癌）动物异种移植模型的体内测定揭示了显着的抗肿瘤功效以及口服生物利用度，在 50 mg/kg 剂量下，最大 TGI 为 36%（腹腔注射）和 44%（口服）。这些发现证实了杂交吡唑啉和咪唑烷-2
• Synthesis and antinociceptive activities of some pyrazoline derivatives
  作者：Zafer Asim Kaplancikli、Gülhan Turan-Zitouni、Ahmet Özdemir、Özgür Devrim Can、Pierre Chevallet

  DOI：10.1016/j.ejmech.2008.09.002

  日期：2009.6

  In the present study, some pyrazoline derivatives were synthesized to investigate their potential antinociceptive activities. 1-[(Benzoxazole/benzimidazole-2-yl)thioacetyl]pyrazoline derivatives were obtained by reacting 3,5-diaryl-1-(2-chloroacetyl)pyrazolines with 2-marcaptobenzoxazole/benzimidazole. The chemical structures of the compounds were elucidated by IR, 1H NMR and FAB+-MS spectral data

  在本研究中，合成了一些吡唑啉衍生物以研究其潜在的抗伤害感受活性。通过使3，5-二芳基-1-（2-氯乙酰基）吡唑啉与2-巯基苯并恶唑/苯并咪唑反应获得1-[（苯并恶唑/苯并咪唑-2-基）硫代乙酰基]吡唑啉衍生物。通过IR，1 H NMR和FAB + -MS光谱数据和元素分析来阐明化合物的化学结构。 所有化合物（100 mg / kg）在热板和乙酸诱导的扭体试验中均显示出显着的抗伤害感受活性。纳洛酮（5 mg / kg）预处理逆转了抗伤害感受活性，表明阿片样物质系统参与了镇痛作用。在Rota-Rod模型中评估时，没有一种化合物会损害动物的运动协调能力。 这些结果支持了以前的论文，这些论文报道了各种苯并恶唑/苯并咪唑-吡唑啉衍生物化合物对阿片类药物的镇痛活性。
• Synthesis and Anticancer Activity of Isatin-Based Pyrazolines and Thiazolidines Conjugates
  作者：Dmytro Havrylyuk、Natalya Kovach、Borys Zimenkovsky、Olexandr Vasylenko、Roman Lesyk

  DOI：10.1002/ardp.201100055

  日期：2011.8

  The synthesis and antitumor activity screening of novel isatin based conjugates with thiazolidine and pyrazoline moieties were performed. Reaction of 3,5‐diaryl‐4,5‐dihydropyrazoles with chloroacetyl chloride yielded starting 2‐chloro‐1‐(3,5‐diaryl‐4,5‐dihydropyrazol‐1‐yl)‐ethanones which were utilized in alkylation of isatin and 5‐bromoisatin. Thus, corresponding 1‐[2‐(3,5‐diaryl‐4,5‐dihydropyraz

  进行了具有噻唑烷和吡唑啉部分的新型靛红基缀合物的合成和抗肿瘤活性筛选。3,5-二芳基-4,5-二氢吡唑与氯乙酰氯反应生成起始的2-氯-1-（3,5-二芳基-4,5-二氢吡唑-1-基）-乙酮，用于靛红的烷基化和 5-溴皂苷。因此，得到了相应的1-[2-(3,5-二芳基-4,5-二氢吡唑-1-基)-2-氧乙基]-1H-吲哚-2,3-二酮(1a-1d)。化合物 1a-1d 已用于与 4-噻唑烷酮的 Knoevenagel 缩合反应，得到一系列 5-亚苯基衍生物 2a-2f 和 3a-3d。测试合成的化合物在 NCI60 细胞系中的抗癌活性。被测化合物中，5-溴-1-2-[5-(4-氯苯基)-3-(4-甲氧基苯基)-4,5-二氢吡唑-1-基]-2-氧乙基}-1H-吲哚-2,
• Synthesis and Antimicrobial Activities of Some 1-[(N, N-Disubstitutedthiocarbamoylthio)acetyl]-3,5-diaryl-2-pyrazolines
  作者：Gülhan Turan-Zitouni、Ahmet Özdemir、Zafer Asim Kaplancikli、Pierre Chevallet、Yagmur Tunali

  DOI：10.1080/104265090930452

  日期：2005.12

  The increasing clinical importance of drug-resistant fungal and bacterial pathogens has lent additional urgency to microbiological research and new antimicrobial compound development. For this put-pose, new pyrazoline derivatives were synthesized and evaluated for antimicrobial activity.Some 1-[(N,N-disubstitutedthiocarbamoylthio)acetyl]-3,5-dialyl-2-pyrazolines derivatives were synthesized by reacting 1-(chloroacetyl)-3,5-diaryl-2-pyrazolines with appropriate potassium salts of secondary amine dithiocarbamic acids. The chemical structures of the compounds were elucidated by IR, H-1-NMR, and FAB(+)-MS spectral data. Their antimicrobial activities against Staphylococcus aureus (B-767), Escherichia coli (B-3704), Pseudomonas aeruginosa (ATCC 27853), Proteus vulgaris (NRLL B-123), and Candida. albicans (NRRL-27077) were investigated. The results showed that some of the compounds have notable activity against S. aureus and C. albicans.
• Synthesis of<i>N</i>-Acyl Triazolyl-Pyrazolines via Acylation Initiated by the Hydrazone Moiety with Carboxylic Acids
  作者：Archana Sivasubramaniyan、Dinesh Murugan、Ranganathan Raja、Sathishkumar Murugan、Shanmugavelan Poovan、Ponnuswamy Alagusundaram

  DOI：10.1080/00397911.2015.1104357

  日期：2015.12.2

  An efficient synthesis of N-acyl/N-substituted acyl pyrazolines and their triazole hybrids have been accomplished via acylation of pyrazolines and pyrazoline-triazole hybrids with carboxylic acids and/or substituted carboxylic acids in the absence of activating agents/catalysts. In the present study, a mechanism envisaging the in situ generation of a new transient acylating intermediate has been proposed to explain the acylation.