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1-(2-methyl-4-chlorophenyl)-3-(2-hydroxyethyl)thiourea | 52266-61-2

中文名称
——
中文别名
——
英文名称
1-(2-methyl-4-chlorophenyl)-3-(2-hydroxyethyl)thiourea
英文别名
1-(4-Chloro-2-methylphenyl)-3-(2-hydroxyethyl)thiourea
1-(2-methyl-4-chlorophenyl)-3-(2-hydroxyethyl)thiourea化学式
CAS
52266-61-2
化学式
C10H13ClN2OS
mdl
——
分子量
244.745
InChiKey
DPAYVMJWTCCUPF-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    1.8
  • 重原子数:
    15
  • 可旋转键数:
    3
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.3
  • 拓扑面积:
    76.4
  • 氢给体数:
    3
  • 氢受体数:
    2

反应信息

  • 作为反应物:
    描述:
    1-(2-methyl-4-chlorophenyl)-3-(2-hydroxyethyl)thiourea盐酸 作用下, 以 为溶剂, 以40%的产率得到2-硫杂氮醇胺,N-(4-氯-2-甲基苯基)-4,5-二氢-
    参考文献:
    名称:
    Synthesis, Insecticidal Activities, and SAR Studies of Novel Pyridylpyrazole Acid Derivatives Based on Amide Bridge Modification of Anthranilic Diamide Insecticides
    摘要:
    Anthranilic diamides are one of the most important classes of modern agricultural insecticides. To discover new structure-modified compounds with high activity, series of novel carbonyl thioureas, carbonyl ureas, oxadiazoles, carbonyl thiophosphorylureas, oxadiazole-containing amides, and thiazoline-containing amides were designed through the modification of the amide bridge based on the structure of chlorantraniliprole and were synthesized, and bioassays were carried out. The compounds were characterized and confirmed by melting point, IR, H-1 NMR, and elemental analyses or HRMS. Preliminary bioassays indicated that some compounds exhibited significant insecticidal activities against oriental armyworm, diamondback moth, beet armyworm, corn borer, and mosquito. Among them, trifluoroethoxyl-containing carbonyl thiourea 20a showed best larvicidal activity against oriental armyworm, with LC50 and LC95 values of 0.1812 and 0.7767 mg/L, respectively. Meanwhile, 20c and 20e showed 86 and 57% death rates against diamondback moth at 0.005 mg/L, and the LC50 values of the two compounds were 0.0017 and 0.0023 mg/L, respectively, which were lower than that of the control chlorantraniliprole. The relationship between structure and insecticidal activity was discussed, and the HF calculation results indicated that the carbonyl thiourea moiety plays an important role in the insecticidal activity. The present work demonstrated that the trifluoroethoxyl-containing carbonyl thioureas can be used as lead compounds for further development of novel insecticides.
    DOI:
    10.1021/jf4012467
  • 作为产物:
    参考文献:
    名称:
    1-Hydroxyalkyl-3-phenylthioureas as novel HDL-elevating agents
    摘要:
    A series of 1-hydroxyalkyl-3-phenylthiourea analogs were prepared and evaluated as HDL-and Apo A-I-elevating agents. Derivatives 5h. 7j, 7n, and 7o were found to be as effective or superior to gernfibrozil (1). (C) 2004 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmcl.2004.10.094
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文献信息

  • 1-Hydroxyalkyl-3-phenylthioureas as novel HDL-elevating agents
    作者:Gary M. Coppola、Robert E. Damon、J. Bruce Eskesen、Dennis S. France、James R. Paterniti
    DOI:10.1016/j.bmcl.2004.10.094
    日期:2005.2
    A series of 1-hydroxyalkyl-3-phenylthiourea analogs were prepared and evaluated as HDL-and Apo A-I-elevating agents. Derivatives 5h. 7j, 7n, and 7o were found to be as effective or superior to gernfibrozil (1). (C) 2004 Elsevier Ltd. All rights reserved.
  • Three-dimensional quantitative structure–activity studies of octopaminergic agonists responsible for the inhibition of sex-pheromone production in Hercoverpa armigera
    作者:Akinori Hirashima、Ada Rafaeli、Carina Gileadi、Eiichi Kuwano
    DOI:10.1016/s0968-0896(99)00189-3
    日期:1999.11
    The quantitative structure-activity relationship (QSAR) of octopaminergic agonists responsible for the inhibition of sex-pheromone production in Hercoverpa armigera, was analyzed using physicochemical parameters, molecular shape analysis (MSA), molecular field analysis (MFA), and receptor surface model (RSM), respectively. The dose-response studies were performed in vitro analyzing the effect of these compounds on intracellular cAMP production in the presence of pheromone biosynthesis activating neuropeptide (PBAN) at 1 pmol/intersegment. Six active derivatives were identified in the order of decreasing pheromonostatic activity: 2-(2,6-dimethylanilino)imidazolide (6) > 2-(2-methyl-4-chloroanilino)oxazolidine (1) > clonidine (5) > 2-(2,6-diethylanilino)thiazolidine (8) > 2-(3,5-dichlorobenzylamino)-2-oxazoline (4) > tolazoline (10) which were all active in the nanomolar range in inhibition of cAMP production by 1 pmol PBAN/intersegment. Four other compounds were less active having K-i in the micromolar range. An MSA was tried to obtain QSAR equation that incorporates spatial molecular similarity data of those compounds. MFA on the training set of those compounds evaluated effectively the energy between a probe and a molecular model at a series of points defined by a rectangular or spherical grid. An RSM was generated using some subset of the most active structures. Three-dimensional energetics descriptors were calculated from RSM/ligand interaction and these three-dimensional descriptors were used in QSAR analysis. These results indicate that these derivatives could provide useful information in the characterization and differentiation of octopaminergic receptor types and subtypes. (C) 1999 Elsevier Science Ltd. All rights reserved.
  • US3950537A
    申请人:——
    公开号:US3950537A
    公开(公告)日:1976-04-13
  • US4009284A
    申请人:——
    公开号:US4009284A
    公开(公告)日:1977-02-22
  • Synthesis, Insecticidal Activities, and SAR Studies of Novel Pyridylpyrazole Acid Derivatives Based on Amide Bridge Modification of Anthranilic Diamide Insecticides
    作者:Bao-Lei Wang、Hong-Wei Zhu、Yi Ma、Li-Xia Xiong、Yong-Qiang Li、Yu Zhao、Ji-Feng Zhang、You-Wei Chen、Sha Zhou、Zheng-Ming Li
    DOI:10.1021/jf4012467
    日期:2013.6.12
    Anthranilic diamides are one of the most important classes of modern agricultural insecticides. To discover new structure-modified compounds with high activity, series of novel carbonyl thioureas, carbonyl ureas, oxadiazoles, carbonyl thiophosphorylureas, oxadiazole-containing amides, and thiazoline-containing amides were designed through the modification of the amide bridge based on the structure of chlorantraniliprole and were synthesized, and bioassays were carried out. The compounds were characterized and confirmed by melting point, IR, H-1 NMR, and elemental analyses or HRMS. Preliminary bioassays indicated that some compounds exhibited significant insecticidal activities against oriental armyworm, diamondback moth, beet armyworm, corn borer, and mosquito. Among them, trifluoroethoxyl-containing carbonyl thiourea 20a showed best larvicidal activity against oriental armyworm, with LC50 and LC95 values of 0.1812 and 0.7767 mg/L, respectively. Meanwhile, 20c and 20e showed 86 and 57% death rates against diamondback moth at 0.005 mg/L, and the LC50 values of the two compounds were 0.0017 and 0.0023 mg/L, respectively, which were lower than that of the control chlorantraniliprole. The relationship between structure and insecticidal activity was discussed, and the HF calculation results indicated that the carbonyl thiourea moiety plays an important role in the insecticidal activity. The present work demonstrated that the trifluoroethoxyl-containing carbonyl thioureas can be used as lead compounds for further development of novel insecticides.
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同类化合物

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